Download Analysis of carbohydrates and glycoconjugates by

ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
BY MATRIX-ASSISTED LASER DESORPTION/IONIZATION MASS
SPECTROMETRY: AN UPDATE FOR THE PERIOD 2005–2006
David J. Harvey*
Department of Biochemistry, Oxford Glycobiology Institute,
University of Oxford, Oxford OX1 3QU, UK
Received 01 December 2008; received (revised) 26 June 2009; accepted 13 July 2009
Published online 10 March 2010 in Wiley Online Library (wileyonlinelibrary.com). DOI 10.1002/mas.20265
This review is the fourth update of the original review, published
in 1999, on the application of MALDI mass spectrometry to the
analysis of carbohydrates and glycoconjugates and brings
coverage of the literature to the end of 2006. The review covers
fundamental studies, fragmentation of carbohydrate ions,
method developments, and applications of the technique to the
analysis of different types of carbohydrate. Specific compound
classes that are covered include carbohydrate polymers from
plants, N- and O-linked glycans from glycoproteins, glycated
proteins, glycolipids from bacteria, glycosides, and various other
natural products. There is a short section on the use of MALDITOF mass spectrometry for the study of enzymes involved in
glycan processing, a section on industrial processes, particularly
the development of biopharmaceuticals and a section on the use
of MALDI–MS to monitor products of chemical synthesis of
carbohydrates. Large carbohydrate–protein complexes and
glycodendrimers are highlighted in this final section. # 2010
Wiley Periodicals, Inc., Mass Spec Rev 30:1–100, 2011
Keywords: MALDI; carbohydrates; glycoproteins; glycolipids
I. INTRODUCTION
This review is a continuation of the four earlier ones in this series
(Harvey, 1999, 2006, 2009) on the application of MALDI
mass spectrometry to the analysis of carbohydrates and
glycoconjugates and is intended to bring the coverage of the
literature to the end of 2006. MALDI continues to be a major
technique for the analysis of carbohydrates although electrospray
is becoming increasingly popular. Figure 1 shows the year-byyear increase in articles reporting use of MALDI for the period
1991–2006. As the review is designed to complement the earlier
work, structural formulae, etc. that were presented earlier are not
repeated. However, a citation to the structure in the earlier work is
indicated by its number with the prefix ‘‘1’’ (i.e., 1/x refers to
structure x in the first review and 2/x to the second). Other reviews
and review-type articles directly concerned with, or including
MALDI analysis of glycoconjugates to have been published
during the review period include general reviews on miniaturized separation techniques including LC/MALDI-TOF/TOF
————
*Correspondence to: David J. Harvey, Department of Biochemistry,
Oxford Glycobiology Institute, University of Oxford, Oxford OX1
3QU, UK. E-mail: [email protected]
Mass Spectrometry Reviews, 2011, 30, 1– 100
# 2010 by Wiley Periodicals, Inc.
(Mechref & Novotny, 2006), solid-phase tools such as microarrays (Larsen et al., 2006), capillary electrophoresis-MS
(Campa et al., 2006; Huck et al., 2006), atmospheric pressure
MALDI (Creaser & Ratcliffe, 2006). More specific reviews
include those on the analysis of polysaccharides (Cui, 2005),
glycoproteins and attached glycans (Aitken, 2005; Morelle &
Michalski, 2005; Budnik, Lee, & Steen, 2006; Geiser, Silvescu,
& Reinhold, 2006; Geyer & Geyer, 2006; Harvey, Dwek,
& Rudd, 2006; Haslam, Khoo, & Dell, 2006a; Haslam, North, &
Dell, 2006b; Kondo et al., 2006; Morelle et al., 2006a),
N- (Harcum, 2005; Harvey, 2005d,e; Medzihradszky, 2005;
Bardor et al., 2006; Jang-Lee et al., 2006) and O-linked
(Peter-Katalinic, 2005) glycosylation, bacterial glycoproteomics
(Hitchen & Dell, 2005), protein glycation (Lapolla et al., 2006;
Niwa, 2006; Silván et al., 2006), GPI anchors (Baldwin, 2005),
proteoglycans (Didraga, Barroso, & Bischoff, 2006), glycosylaminoglycans (Gama & Hsieh-Wilson, 2005; Pojasek, Raman, &
Sasisekharan, 2005; Sasisekharan et al., 2006), glycosphingolipids (Levery, 2005; Zheng, Wu, & Hancock, 2006b), and
flavonoids (de Rijke et al., 2006). The book on mass spectrometry
in biophysics by Kaltashov and Eyles (2005) also contains
information.
II. THEORY
Knochenmuss (2006) has summarized ion formation mechanisms in UV MALDI and emphasized that a two-step mechanism
of ionization during or shortly after the laser pulse, followed
by secondary reactions in the expanding plume of desorbed
material is gaining acceptance. He concludes by saying that: ‘‘To
the extent that local thermal equilibrium is approached in the
plume, the mass spectra may be straightforwardly interpreted in
terms of charge transfer thermodynamics.’’
Gas-phase cationization has been demonstrated in an
experiment in which two target spots were prepared and
illuminated simultaneously with the laser. One spot contained
polyethylene glycol (PEG) and dihydroxybenzoic acid (DHB,
1/26), whereas the other contained DHB and lithium hydroxide.
Even though the PEG and lithium did not come into contact on the
target, [M þ Li]þ ions were observed in the spectrum. However,
because of difficulties in removing residual Naþ and Kþ from the
DHB, the authors could not conclude that gas-phase cationization
was the only or major process operating under normal MALDI
conditions (Erb, Hanton, & Owens, 2006).
&
HARVEY
A. High-Pressure and Atmospheric Pressure
MALDI (AP-MALDI)
Atmospheric pressure MALDI produces ions with less internal
energy than vacuum MALDI and has been used to produce
spectra of sialylated N- and O-linked glycans and gangliosides
without substantial loss of the sialic acid that is a regular feature
of vacuum MALDI (Zhang, Fu, & Ning, 2005a). A mixture of
DHB and 2,5-dihydroxyacetophenone (DHA, 1/43) was used as
the matrix and spectra were recorded with an FT-ICR mass
spectrometer.
IV. MATRICES
A. Theory of Matrix Action
FIGURE 1. Number of articles published on the application of
MALDI–MS to carbohydrate research by year.
Sodium cation affinities of hydroxybenzoic acid isomers
have been published (Chinthaka et al., 2006). In general the most
stable binding conformations involved formation of a hexacyclic
chelation ring involving the carboxyl carbonyl group and a
hydroxy group in the 2-position. Proton affinities and gas-phase
basicities for the DHB isomers have been calculated using
density functional theory and shown to be in good agreement with
values obtained by FT-ICR (Rebber et al., 2006). Mesaros et al.
(2006) have studied the photophysics of common MALDI
matrices and found that 2,4,6-trihydroxyacetophenone (THAP,
1/44) and DHB release heat to the medium more efficiently than
matrices such as harmane (1/34) and nor-harmane (1/35) and
behave as ‘‘hotter’’ matrices.
The observation that thin MALDI samples can perform
differently than thicker samples on metal substrates has been
investigated by Knochenmuss, McCombie, and Faderl (2006) for
three electrosprayed matrixes, DHB, sinapinic acid (SA, 1/48),
and a-cyano-4-hydroxycinnamic acid (CHCA, 1/23), on stainless steel and gold substrates. Thin sample enhancement was
found in both polarities for all three matrices on a steel substrate.
On gold, only CHCA showed enhancement. Two models were
used to evaluate the data. The first was based on one-photon
photoelectron emission from the metal, and the second on twophoton matrix ionization at the metal interface. The surfaceenhanced matrix photoionization model best fitted the evidence,
including the fluence-dependence of electron emission from
DHB on steel.
III. INSTRUMENTATION
A pyroelectric lead–lanthanum–zirconate–titanate ceramic
plate has been developed as a MALDI target which allows
spectra of thermally unstable compounds such as carbohydrates
to be obtained without the use of a matrix (Sato et al., 2005). a(4/24) and b-cyclodextrins (4/6) in the presence of sodium iodide
gave strong [M þ Na]þ ions with no sign of fragmentation.
2
Although incorporation of the analyte into the crystal has been
thought to be necessary for the MALDI process to occur, a recent
study has shown that this probably is not the case and that
intimate contact between analyte and the crystal surface is more
important. The study showed that the strength of the MALDI
signal was approximately inversely proportional to crystal size
suggesting that contact between the analyte and the matrix
surface was more important (Trimpin, Räder, & Müllen, 2006).
B. Simple Matrices
2-[(2E)-3-(4-tert-butylphenyl)-2-methylprop-2-enylidene]malononitrile (DCTB, 1) has been shown to be an effective matrix for
hydrophobic compounds but less so for compounds soluble in
water. Nevertheless, derivatized sugars and glycosides could be
induced to fly with the formation of the normal [M þ metal]þ ions
(Wyatt, Stein, & Brenton, 2006).
Pencil ‘‘lead’’ (a mixture of graphite, clay, and waxes) has
been shown to be an effective matrix for several types of
compound including cyclodextrin. The matrix has the advantage
of the absence of low mass matrix ions that characterize the
spectra recorded from most other matrices making it ideal for
small molecules although carbon clusters are often seen and,
depending on the pencil, various constituents of the ‘‘lead’’ can
give signals (Black et al., 2006).
Carbon nanotubes were reported in 2003 as effective
matrices for carbohydrates (Xu et al., 2003). However, a problem
was keeping them on the MALDI target. This problem has
been solved by attaching them to the target with polyurethane
adhesive prior to adding the glycan solution (Ren et al., 2005).
This procedure retained the property of the matrix to produce
signals without the low-mass matrix ions. Oxidized carbon
nanotubes have been reported to give better results than carbon
nanotubes themselves because of their greater solubility in water
(Pan et al., 2005). They have been used to record MALDI spectra
from honeysuckle constituents (Chen et al., 2006c).
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Schulz et al. (2006) have compared the degree of analyte
fragmentation in AP-MALDI as a function of the matrix and
laser fluence. Several analytes were employed and the matrix
hardness/softness was found to be consistent when comparing
the analytes. The consensus ranking from hardest to softest
was: CHCADHB>SA THAP > 6-azo-2-thiothymine (ATT,
1/45) > hydroxypicolinic acid (HPA, 1/60) although the exact
ranking could be fluence dependent. Of several matrix properties,
sublimation or decomposition temperature (determined using
thermogravimetry), analyte initial velocity, and matrix proton
affinity, the best correlation was found with the matrix proton
affinity.
&
liquid matrices 1-methylimidazolium (4 þ 1/23) a-cyano-4hydroxycinnamate and tetrabutylammonium (Bu4N þ 1/26)
2,5-dihydroxybenzoic acid have produced signals from sucrose
octasulfate (5) and an octasulfated pentasaccharide as their
sodium salts. No ion pairing was necessary but some loss of
sulfate was seen (Laremore et al., 2006).
C. Binary Matrices
Lewandrowski, Resemann, and Sickmann (2005) have noted that
a mixed matrix of DHB and ATTwas useful in reducing in-source
fragmentation of sialylated glycans. A novel MALDI matrix
consisting of DHB and aniline has been reported to produce a
significant increase in signal for N-linked glycans compared with
the signal obtained with DHB alone (Snovida, Chen, & Perreault,
2006). The presence of aniline produced an on-target derivatization of the glycans via Schiff base formation with the reducing
end GlcNAc residue without the need for prolonged incubation
periods and elevated temperatures. The reaction appeared to be
occurring slowly even after the sample-matrix spot had dried and
could be used to differentiate glycans and peptides because the
latter compounds did not react.
The use of added quaternary ammonium or phosphonium
salts to matrices has allowed fragile sulfated and sialylated carbohydrates to be analyzed without decomposition.
For sulfates such as heparin disaccharide (a-DUA-2S(1 ! 4)GlcNS-6S), the combination of 2-amino-5-nitropyridine
(2/20) and tetraphenylphosphonium bromide (2) gave the best
results. Signals were produced both in positive and negative ion
modes. In positive ion mode, species such as [M þ Pnþ1]þ were
observed where n ¼ the number of acid groups. For sialylated
glycans such as gangliosides, a combination of THAP with
dimethylpalmitylammonium bromide (3) was the system of
choice (Ueki & Yamaguchi, 2005).
E. Negative Ions from Neutral Glycans
In general, neutral carbohydrates do not give negative ions with
the common matrices such as DHB. However, they can be made to
form adducts with anions such as chloride with b-carboline
matrices, such as nor-harmane (1/35) if ammonium chloride is
added (Suzuki, Yamagaki, & Tachibana, 2006). These authors
(Suzuki, Yamagaki, & Tachibana, 2005) have also used
ammonium chloride with a harmine (1/36) matrix to produce
[M þ Cl] ions and noted that the best results were obtained when
the ammonium chloride was added in the same amount as the
matrix. A layered target consisting of matrix, analyte and additive
gave the best results. Although addition of salts is usually
detrimental to signal strength in positive ion mode, the authors of
this work report that the ionization efficiency for the production of
[M þ Cl] ions increases in the presence of an excess of
ammonium chloride. Laštovicková and Chmelı́k (2006) have
obtained negative ion spectra of carbohydrates such as inulin (6)
directly from the five matrices DHB, THAP, CHCA, 3-aminoquinoline (3-AQ, 1/24) and HABA. Of these, THAP was by far the
best. 3-AQ gave a spectrum displaying smaller carbohydrates.
Spectra were recorded with a 4700 TOF/TOF instrument.
Carbohydrates such as inulin without a reducing terminus gave
[M H] ions but reducing sugars could be identified by formation of an [M-120] ion as the result of a cross-ring fragmentation.
D. Liquid Matrices
Two reviews on ionic liquid matrices have appeared (Koel,
2005; Tholey & Heinzle, 2006) and two other more general
reviews (Jain et al., 2005; Liu, Jönsson, & Jiang, 2005)
have included their use. Although polysulfated sugars usually
do not give signals under conventional MALDI conditions, the
Mass Spectrometry Reviews DOI 10.1002/mas
3
&
HARVEY
V. DERIVATIVES
Derivatization of carbohydrates, mainly of the reducing terminal
by reductive amination, has been reviewed (Anumula, 2006).
A. Reducing Terminal Derivatives
Sekiya et al. (2005b) have reported that N-linked glycans, when
derivatized with 2-aminpyridine (2-AP, 1/52) but not with 2aminobenzamide (2-AB, 1/56) and when ionized from DHB,
produce, in addition to the normal [M þ Na]þ ions, additional
[M þ H]þ ions that are accompanied by another ion two mass
units higher. This apparently reduced product does not
accompany the [M þ Na]þ ion, is not seen with nor-harmane as
the matrix or on electrospray ionization. However, the abundance
of the [M þ H þ H2]þ ion was enhanced when the reductive
matrix 1,5-diaminonaphthalene (1/70) was used. The authors
proposed, on the basis that all ions in the MS/MS spectra were
shifted by two mass units from their positions in the spectra of the
[M þ H]þ ions, that the reaction involved reduction of the
pyridine ring of the 2-AP derivative.
A comparison of ions formed by three different derivatives
have shown that 2-AB and phenylhydrazone derivatives
produced [M þ Na]þ under MALDI conditions whereas 1phenyl-3-methyl-5-pyrazolone (PMP, 7) produced a mixture of
[M þ Na]þ, [M þ H]þ and [M H þ 2Na]þ ions. Phenylhydrazones and PMP derivatives produced more abundant cross-ring
cleavage ions in the PSD spectra of complex glycans whereas, for
high-mannose glycans, more informative spectra were provided
by the 2-AB derivatives and phenylhydrazones (Lattová et al.,
2005). Formation of phenylhydrazones, either ‘‘in-tube’’ or on
the MALDI target has been reported to improve detection of
released glycans in the presence of peptides (Lattová et al., 2006).
The spectra of a mixture of these compounds showed both an
increase in the signal from the glycans and a decrease in the
abundance of the peptide signals.
A multifunctional tag combining UV activity with bioaffinity has been described (Hsu, Chang, & Franz, 2006). The tag
(8) was synthesized by activating biotin (9) with 1,10 -carbonyl
diimidazole and coupled to one of the aminomethyl groups of
xylylenediamine. The other amino group was available for
reductive amination of the carbohydrate. The tag was used for
labeling linear oligosaccharides, milk sugars, and high-mannose
glycans from ribonuclease B. Quaternization of the amino group
with methyl iodide gave a positively charged species and an
increase in sensitivity of 10-fold such that amounts as little as
100 fmol on-probe could be detected. The presence of the tag
did not affect fragmentation which occurred by cleavage of
the sugar.
4
Xia et al. (2005a) have derivatized a range of glycans with
2,6-diaminopyridine (10) by reductive amination to give a
fluorescent derivative with a free amino group that could be
conjugated with a range of other compounds such as Nhydroxysuccinimide-activated glass slides, maleimide-activated
proteins, carboxylated microspheres and biotin (10). Products
were ionized by MALDI-TOF–MS.
A method for removing the derivative from reductively
aminated glycans has been reported and involves incubation at
308C with a solution of hydrogen peroxide/acetic acid.
Recoveries were in the region of 90% (Suzuki, Fujimori, &
Yodoshi, 2006).
B. Reducing-Terminal Derivatives Prepared by
Other Methods
N-glycans are released with protein-N-glycosidase F (PNGase F)
as glycosylamines that are rapidly hydrolyzed to the native
sugars, particularly at low pH. Consequently, if the reaction is
performed rapidly, they can be labeled by reaction with carbonyl
compounds in what is essentially the reverse of the normal
reductive amination procedure. Kamoda et al. (2005) have made
use of this reaction to prepare in situ Fmoc derivatives by reaction
with 9-fluorenylmethyl chloroformate (11) which they claim
gave a fivefold increase in fluorescence detection compared with
2-aminobenzoic acid (2-AA, 1/57) derivatives. Furthermore, the
free sugars could be recovered by incubation with morpholine in
dimethylformamide. The derivatives gave good MALDI-TOF
spectra from DHB.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
C. Derivatives of Other Sites
A solid-phase method for permethylation of small amounts of
carbohydrates has been developed and consists of microcolumns
packed with sodium hydroxide powder through which is passed a
solution of the carbohydrates in DMSO containing traces of
water. Effective permethylation was reported to take less than
1 min and both oxidative degradation and peeling reactions
were minimized. The need for excessive clean-up was also
avoided although the glycans had to be separated from the DMSO
with chloroform in the conventional manner. MALDI-TOF
spectra were then obtained directly from DHB (Kang et al.,
2005).
Permethylation of carbohydrates frequently produces compounds 30 mass units higher than that of the product which,
until now have not been characterized. These compounds have
now been identified as containing a methoxy-methyl group in
place of one of the methyl groups, its source being reaction with
iodomethyl methyl ether produced as a by-product of the
methylating reagents (Robinson, Routledge, & Thomas-Oates,
2005). Permethylation in general has been reviewed by Ciucanu
(2006).
The problem of signal suppression of small glycopeptides in
the presence of larger peptides has been successfully addressed
by formation of derivatives with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC). Glycopeptides from human
antithrombin, chicken ovalbumin, and bovine a1-acid glycoprotein could be detected in low fmol amounts (Ullmer, Plematl,
& Rizzi, 2006).
Sialic acids have been stabilized for MALDI analysis by
conversion to amides by reaction with ammonium bicarbonate/
ammonium chloride in the presence of 4-(4,6-dimethoxy-1,2,3triazil-2-yl)-4-methylmorpholinium chloride (DMT-MM, 12)
for 24 hr at 508C (Sekiya, Wada, & Tanaka, 2005). Masses were
1 unit/sialic acid less than those of the underivatized molecules
and their MS/MS spectra (positive ion) were very informative
with a wealth of B- and Y-type glycosidic cleavage products.
Methyl ester formation can achieve similar stabilization; this
reaction, or its equivalent, has been proposed as a necessary step
for detecting sialylated glycans with the Shimadzu quadrupole
ion trap-TOF (QIT-TOF) instrument where there is considerable
loss of sialic acid (1/11) as the result of post-source decay
(Mandato et al., 2006).
&
0.5 mg) in 2H2O (200 mL) containing 10% 2H3-acetonitrile (the
acetonitrile was necessary to ensure the complete solubility of the
matrix). The solution was lyophilized and redissolved in 2H2O
(100 mL) plus 2H3-acetonitrile (25 mL) immediately prior to
spotting 0.5 mL onto an ice-cold, stainless steel target. The target
was stored in an airtight polyethylene container at 208C over
Dryrite and, after 24 hr, was transferred to the spectrometer inlet.
To minimize the condensation of atmospheric water onto the cold
target, this transfer was made with the inlet to the mass
spectrometer enclosed inside a nitrogen-flushed glovebox. The
method was applied to several sugars including malto- and xylopyranoses, a- (4/24) and b-cyclodextrins (4/6), stachyose (1/19),
chitotetraose (13), and erythromycin (4/4).
VI. CLEAN-UP OF SAMPLES PRIOR TO
MALDI ANALYSIS
A. Trapping of Glycans and Glycoproteins
Lee et al. (2005e) have prepared magnetic beads linked to 4aminophenylboronic acid (14) and used the ability of the boronic
acid to form cyclic boroxanes with carbohydrates to isolate
glycoproteins from solution. The bound glycoproteins were
removed with a magnet and transferred directly to the MALDI
target from which spectra were recorded from sinapinic acid.
CHCA was used for tryptic peptides derived directly from the
bound glycoproteins. Similar beads have been used to enrich
glycated insulin (Farah et al., 2005). Sparbier, Wenzel, and
Kostrzewa (2006) have used magnetic beads functionalized with
ConA, wheat germ agglutinin (WGA) or 3-aminophenyl-boronic
acid to extract glycoproteins from human serum. Analysis of the
enriched serum proteins by tryptic digestion and MALDI-TOF/
TOF MS/MS analyses revealed the specific binding of nine
glycosylated proteins by ConA, eight glycosylated proteins by
WGA and eight glycoproteins by boronic acid. Only four nonglycosylated peptides were identified. Each bead type presented
its own individual binding profile overlapping with the profiles
of the two others. A method has been reported for enrichment of
O-GlcNAc-modified peptides by use of lectin affinity chromatography with wheat-germ agglutinin as the lectin (Vosseller
et al., 2006). The method was successfully used to enrich 145
unique O-GlcNAc-modified peptides from a post-synaptic
density preparation.
D. Carbohydrates Labeled with Stable Isotopes
Hydrogen–deuterium exchange can be used for studies of
carbohydrate structure and carbohydrate–protein interaction but
has been plagued by back-exchange of deuterium by hydrogen.
Price (2006) has now reported a method for optimization of the
deuteration reaction and for minimizing back exchange.
Typically, the exchange reactions involved mixing the carbohydrate sample (0.2–0.3 mg) and DHB (0.5 mg; oxalic acid,
Mass Spectrometry Reviews DOI 10.1002/mas
Nanoparticles whose surfaces have aminooxyl groups have
been developed for extracting carbohydrates from biological
5
&
HARVEY
matrices (Niikura et al., 2005). Reducing carbohydrates reacted
with the amino groups of the nanoparticles to form oximes
and the complexes were isolated by centrifugation. The glycans
were then released under acidic conditions. The method was
demonstrated with N-glycans released from ovalbumin. Before
nanoparticle treatment, no glycans were observed in the reaction
mixture but after treatment, only signals from the glycans were
present.
A method for trapping released glycans by chemical
reaction with a water-soluble polymer carrying reactive amino
groups has been developed (Nishimura et al., 2005). After
isolating the complex, the sugars could be released and examined
by MALDI-TOF. Experiments were conducted with N-glycans
released from human immunoglobin (IgG) and profiles similar to
those obtained by HPLC were observed.
B. Use of Resins
Yu et al. (2005c) from Waters Corporation, Milford, MA, have
reported the use of hydrophilic interaction chromatography
(HILIC) sorbent to clean sugars after PNGase release. The
sorbent was packed into a 96-well microelution device which was
operated with a vacuum manifold. Each well was washed with
Milli Q water and conditioned with 200 mL of 90% MeCN. The
deglycosylated sample was diluted with MeCN (20 mL glycan
solution to 180 mL MeCN to bring the organic concentration to
90%) and loaded onto the HILIC plate. Salts, detergent, and
protein residues were washed out with 200 mL of 90% MeOH/
water after which the glycans were eluted with 20–50 mL 10 mM
ammonium citrate in 25% MeCN (pH 8). Recovery was
estimated to be 70% using a RapiGest surfactant to denature
the glycoproteins prior to enzymatic glycan release (see below)
and both MALDI-TOF and MALDI-Q-TOF spectra were
reported from DHB for folate-binding protein, ovalbumin and
IgG glycans. HILIC clean-up has also been demonstrated by
Thaysen-Andersen and Højrup (2006) for glycopeptides from
bovine fetuin.
Many other resins have been used in the review period; some
of these are C18 to remove peptides (Parry et al., 2006b),
cellulose cartridges (Higai et al., 2005) and GlycoClean H
cartridges (Prozyme, San Leandro, CA), (Wong, Yap, & Wang,
2006) for N-glycans. High salt content has been removed with a
Microcon YM-10 centrifugal filtering device with a low-binding,
anisotropic, hydrophilic cellulose membrane with a nominal
mass limit of 10,000 (Mechref, Muzikar, & Novotny, 2005).
VII. QUANTIFICATION
amine stock solution and a 10% acetic anhydride solution in
dioxane. Treatment of the reaction mixture with 10 mL of a 26%
aqueous ammonia solution resulted in the hydrolysis of O-acetyl
groups and gave N-acetylglucosamine-6P as a single product.
Spectra were recorded in negative ion reflectron mode with
THAP as the matrix and good linearity and reproducibility were
reported.
VIII. FRAGMENTATION
By use of an enzymatic reaction, biantennary N-linked glycans
have been prepared in which one of the galactose rings contained 13C. Positive ion fragmentation with a MALDI-QIT-TOF
instrument showed preferential elimination of Gal-GlcNAc
moieties from the 6-antenna. This represents one of the few
studies in which stable isotope labeling has been used to study
details of the fragmentation mechanisms undergone by N-linked
glycans (Kato et al., 2004).
A. Post-Source Decay (PSD)
Post-source decay (PSD) studies on isomeric trehaloses have
shown that Y-type fragments are most abundant from the
a,a-isomer (3/39) as predicted from theoretical calculations.
Use of hydroxy-deuterated trehaloses showed an isotope effect
that was greatest for the b,b-isomer (17) but this could not be
explained purely on vibrational effects and was probably related
to molecular conformation (Yamagaki, Fukui, & Tachibana,
2006). Takashiba et al. (Takashiba, Chiba, & Jigami, 2006) have
studied the fragmentation of phosphorylated high-mannose
glycans from yeast mannan and noted that, whereas the HPO3Man bond is stable, the mannose-a-1-PO3 (18) bond is not. The
position of the phosphate residue in the 3-antenna could be
determined by the masses of Y-type fragments (positive ion
mode). PSD spectra of g-cyclodextrin (1/65) and the isomeric
maltosyl-a-cyclodextrin (19) contained fragment ions at the
same masses (loss of glucose fragments) but at different relative
abundances, allowing the isomers to be differentiated (Yamagaki,
2005).
A method for quantification of glucosamine-6-phosphate (15) as
an assay for glucosamine-6-phosphate synthase has been
developed (Maillard et al., 2006). N-(13C2)-acetylglucosamine6-phosphate (16) was used as the internal standard because
it could be prepared with use of the commercially available
13
C2-acetic anhydride. However, this method necessitated
N-acetylation of the analyte in the enzyme-buffered mixture
under conditions that were compatible with MALDI analysis.
The adopted conditions involved the use of a 0.7 M trimethyl6
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
B. Collision-Induced Dissociation (CID)
High-energy CID spectra obtained with a TOF/TOF instrument
have again been shown to produced enhanced abundance of
cross-ring cleavage, particularly X-type, ions (Lewandrowski,
Resemann, & Sickmann, 2005; Yu, Wu, & Khoo, 2006). Some
protonated fragment ions were observed in the CID spectra of
sodiated precursors when DHB was used as the matrix but the
reason for their formation was unclear. Kurogochi and Nishimura
(2004) had previously reported the formation of such ions and
observed that they could be suppressed with CHCA. However,
it was also noted that this matrix suppressed formation of the
cross-ring products.
Mechref, Kang, and Novotny (2006) have used permethylation and the high-energy fragmentation available with the 4700
TOF/TOF instrument to produce cross-ring fragments from
sialylated glycans and have reported that 0,4A2, 3,5A2, and
2,4
A3/2,4X1 ions at m/z 458.2, 486.3, and 588.4 are present only in
the spectra of glycans containing an a-(2 ! 6)-linked sialic acid.
In branched structures, ions were found that enabled branchspecific linkage to be determined.
A TOF instrument with a curved field reflectron has been
modified by the inclusion of a collision cell to enable high-energy
spectra to be obtained (Belgacem et al., 2006). The resulting
spectrum of Man8GlcNAc2 (20) contained abundant X-type
cleavage fragments that were not seen in the low energy
spectrum.
Most fragmentation of neutral glycans is acquired in positive
ion mode because of the reluctance of the compounds to form
negative ions. However, Wuhrer and Deelder (2005) have
reported that N-glycans labeled with 2-AB give strong [M H]
ions in negative ion mode from an ATT matrix. Fragmentation of
these ions in a TOF/TOF mass spectrometer by laser-induced
Mass Spectrometry Reviews DOI 10.1002/mas
&
dissociation (LID) gave spectra dominated by C and cross-ring
fragments reminiscent of those from PSD spectra of [M þ Cl]
ions reported by Yamagaki, Suzuki, and Tachibana (2005) and
low-energy electrospray-CID spectra of various adducts reported
by Harvey (2005a,b,c). Fragments from these negative ions
provide much more informative spectra than those in positive ion
spectra.
Comparisons of the MS2 fragmentation of [M þ H]þ and
[M þ Na]þ ions from 2-AP-labeled complex N-linked glycans
in a MALDI-QIT instrument have shown that, whereas the
[M þ H]þ ions yielded mainly Y-type cleavage ions, the
[M þ Na]þ ions gave a wealth of B-, Y- and cross-ring product
ions that provided much more structural information. Isomeric
monogalactosylated biantennary glycans (21, 22) could be
differentiated by relative intensity differences in some of the
fragment ions in the MS2 spectra of the [M þ Na]þ ions (Ojima
et al., 2005). MSn spectra recorded with this instrument have
also allowed isomeric milk sugars to be differentiated (Suzuki
et al., 2005b).
Fukui et al. (2006) have performed quantum-mechanical
calculations on sodiated ions of small oligosaccharides and have
attempted to compare their results with the observed spectra with
an AXIMA QIT instrument to determine the Naþ affinity for
several binding positions and the dependence of fragmentation
on the location of sodium. The Na position was less crucial in
terms of the resulting fragment ions for the loss of Fucp and
Neup5Ac because of the acidic functionality and electronegativity of the Neup5Ac and Fucp residues. The calculated
structures for the oligosaccharides containing Manp as a
reducing end and GlcpNAc indicated an increase in stability
with an increasing number of oxygen atoms interacting with the
Naþ ion. The preferred calculated position of Na was in the
vicinity of GlcNAc residues, which was consistent with the
experimental results.
7
&
HARVEY
1. Multiple Successive Fragmentation (MSn)
Takemori, Komori, and Matsumoto (2006) have developed a
method for glycoprotein analysis that involves in-gel tryptic
digestion and analysis of the resulting tryptic glycopeptides with
a MALDI-QIT-TOF MS. Fragmentation at the MS2 and MS3
stages involved mainly the glycan portion of the molecules and
the technique was used to characterize N-linked glycopeptides
from Drosophila cuticle protein.
The advantages of using negative ion MS/MS for sugar
analysis have been stressed and applied to the ion-trap MSn
fragmentation of mono-to hexa-saccharides that mimic the
terminal epitopes of the O-antigens from Vibrio cholerae O:1,
serotypes Ogawa and Inaba. The two strains are differentiated by
the presence of a methoxy group at C2, the chain linkage position,
in the Ogawa strain. The fragmentation patterns allowed the two
serotypes to be differentiated (Bekesová et al., 2006). The
compounds could also be differentiated in positive ion mode with
a TOF/TOF instrument (Kovácik et al., 2006). Reinhold’s group
have made considerable use of this technique. Several examples
are included in the tables below and, in addition, they have
developed software for analysis of the resulting spectra as
described in the section on Computer Analysis of Spectra.
C. Other Methods
Laser-induced (157 nM) photofragmentation has been compared
with CID with a TOF/TOF instrument. Cation-derivatized
carbohydrates (e.g., derivatized with Girard’s T reagent, 1/55)
produced spectra containing abundant cross-ring cleavage ions
with better coverage than provided by low or high energy CID.
On the other hand, native (underivatized) carbohydrates gave
better results by CID (Devakumar, Thompson, & Reilly, 2005).
Normal-phase HPLC coupled off-line to MALDI-TOF/TOF
MS/MS has been reported to be a good method for isomer
differentiation (Maslen et al., 2006). The TOF/TOF instrument
produced abundant cross-ring fragment ions revealing linkage
information. Two ions were found from 2-AA-derivatized
paucimannosidic glycans that were diagnostic for the presence
of an a-(1 ! 3)-linked fucose residue. Formation of one of these
was proposed to involve direct interaction of the acid group of the
derivative with the fucose as proposed in Scheme 1.
D. Internal Residue Losses
Additional problems have been reported for fragmentation of
protonated glycans as the result of internal rearrangements
(Wuhrer et al., 2006c). Biantennary glycans (4/23) with either
the Gal-b-(1 ! 4)-[Fuc-a-(1 ! 3-]-GlcNAc-b-1 ! or GalNAcb-(1 ! 4)-[Fuc-a-(1 ! 3-]-GlcNAc-b-1 ! antennae, free or 2AB labeled, showed migration of fucose between antennae so
that difucosylated antennae could be deduced erroneously. The
transfer did not occur from the core fucose, and was not observed
for sodiated adducts or for permethylated glycans.
E. Fragmentation of Negative Ions
In-source decay (ISD) of [M H] ions from small neutral
carbohydrates can be produced from the matrix nor-harmane and
these ions fragment to give abundant cross-ring cleavage
products yielding linkage information. PSD fragmentation of
[M þ Cl] ions is similar with all fragments being deprotonated
following loss of HCl (Yamagaki, Suzuki, & Tachibana, 2005).
PSD fragmentation of the [M þ Cl] ion from lactooligosaccharides (e.g., 23, 24) produces prominent A-type cross-ring
cleavage ions from the reducing-terminal glucose residues
whereas CID fragmentation in an ion trap is dominated by Ctype glycosidic cleavages similar to those seen with Q-TOF
instruments. The differences have been attributed to collisional
cooling of the [M þ Cl] ions in the trap and the possibility that
these ions decompose in the flight tube in the PSD experiment to
give deprotonated molecules that then rapidly decompose
(Yamagaki, Suzuki, & Tachibana, 2006a,c). The very specific
fragmentation processes occurring in the negative ion spectra of
neutral sugars results in ions that are specific to certain isomers.
Yamagaki, Suzuki, and Tachibana (2006b) have shown that
measurements of the ratio of such ions in mixtures of isomers can
be used to estimate the percentage of each because there is a
linear relationship between ion abundance and percent of a
compound in a mixture. Furthermore, it was noted that C ions are
often very abundant adjacent to HexNAc residues and a
mechanism involving transfer of the amide proton to the negative
site at the cleaved oxygen was proposed.
F. Infrared Multiphoton Dissociation (IRMPD)
A comparison of the CID and IRMPD spectra of 39 mucin-type
O-glycans has shown that they yield nearly identical spectra
corresponding to the lowest energy fragmentation pathways
(Zhang, Fu, & Ning, 2005b). However, fragmentation efficiency
of IRMPD was reported to be better that that for CID for the larger
glycans (above m/z 1400). Both IRMPD and CID produced
similar fragmentation patterns from N-glycans although IRMPD
has been reported to yield more cross-ring cleavage products with
the mannose branch points being particularly susceptible to
cleavage (Lancaster et al., 2006).
SCHEME 1
8
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
G. LIFT-TOF
H. Computer Analysis of Spectra
Kamekawa et al. (2006) have investigated a combination of
frontal affinity chromatography (FAC) and MALDI LIFT-TOF/
TOF MS of four groups of the 2-AP derivatives of structural
isomers and have shown that most can be differentiated by mass
spectrometry. However, two pairs, lacto-N-tetraose/lacto-N-neotetraose (LNT/LNnT, 23/24) and lacto-N-hexaose/lacto-N-neohexaose (LNH/LNnH, 25/26) that differed in having either a
b-(1 ! 3)- or b-(1 ! 4)-linked galactose residue at the reducing
terminus (type 1 and type 2 chains, respectively) could not. FAC,
however, did differentiate these isomers; a galectin from the
marine sponge Geodia cydonium (GC1) and a plant seed lectin
from Ricinus communis (RCA-I) were used for identification of
these chains, respectively emphasizing the importance of the
combination of FAC with mass spectrometry.
Following the demise of CarbBank, there have been several
initiatives to construct glycan databases and tools for glycomics.
One such source is the Kyoto Encyclopedia of Genes and
Genomes (KEGG, http://www.genome.jp/kegg/glycan). This
resource contains a database of carbohydrate structures
(GLYCAN), glycan-related biochemical pathways and a map
illustrating all possible variations of carbohydrate structures
within organisms (composite structure map, CSM). GLYCAN
also includes a structure drawing tool (KegDraw) and a glycan
search and alignment tool (KEGG Carbohydrate matcher,
KCaM) (Hashimoto et al., 2006). A similar web source is
GLYCOSCIENCES.de portal (http://www.glycosciences.de). Its
database contains references, structures, compositions, NMR
shifts, mass spectral fragments (theoretically calculated), and
protein database references (Lütteke et al., 2006). Similar
information can be found from the Consortium for Functional
Glycomics (http://www.functionalglycomics.org) (Raman et al.,
2006). Reviews of available databases relating to glycomics have
been published (Raman et al., 2005; von der Lieth, Lütteke, &
Frank, 2006) and web-based tools available for glycan analysis
are discussed in a review by Pérez and Mulloy (2005).
A program called ‘‘Cartoonist’’ has been developed to
annotate MALDI spectra with structures chosen from a library.
The software takes account of the biosynthetic pathways
involved and gives each plausible structure a confidence score
(Goldberg et al., 2005). ‘‘CartoonistTwo’’ proposes structures for
O-linked glycans by automatically analyzing fragmentation
spectra and is reported to be an improvement on previous
versions of the software because of its scoring function which is
more able to differentiate similar structures. In an evaluation with
O-glycans from Xenopus egg jelly, the software’s predictions
agreed with manual determination in 50% of the spectra. The
first or second highest scoring structure agreed with manual
determination 90% of the time (Goldberg et al., 2006).
The StrOligo algorithm (Ethier et al., 2002, 2003) for
assigning structures to N-linked glycans, developed by the
Manitoba group and described in the earlier review (Harvey,
2008a), has been compared with more conventional techniques in
an investigation of N-glycans, as 2AB derivatives, from human
integrin a5b1 (Ethier et al., 2005). The algorithm identified many
of the constituent glycans but polysialylated glycans were
problematic and isomeric compounds could not be resolved.
The authors recommended using it in combination with more
traditional techniques such as exoglycosidase digestion and
multistage MS/MS.
The program GlycoX is designed to predict the compositions of glycans and glycosylation sites of glycans attached to
small peptides of the type obtained by pronase digestion (An
et al., 2006b). The program takes, as input, the exact mass of the
peptide and the glycan spectra in the form of a mass/intensity
table and computes both the site and the glycans attached to that
site. It has predicted correct glycan compositions for several
model glycoproteins. N-glycosylation sites can be predicted
with the NetNGlyc server at http://www.cbs.dtu.dk/services/
NetNGlyc/.
In a series of three articles from Reinhold’s laboratory, a
MSn method is described for structural analysis of permethylated
X-Type fragments have also been reported from 2-ABderivatized tetra-, penta-, and hexa-saccharides recorded on a
TOF/TOF instrument with LIFT technology (Morelle et al.,
2005b). Weak X-type fragments were also present in fragmentation spectra of permethylated glycans studied by Wuhrer and
Deelder (2006) in experiments that involved the CID fragmentation of ISD fragments produced in the ion-source of a LIFT MS/
MS instrument. Permethylation allowed distinction between
terminal, monosubstituted and disubstituted monosaccharides
and indicated the oligosaccharide sequence. Substitution positions were deduced based on characteristic cross-ring
fragmentation induced by the high-energy collision-induced
fragmentation. As an example of the results, fragmentation of the
B-ion ion resulting from loss of the reducing terminal GlcNAc
residue enabled two isomeric Man3GlcNAc2 N-linked isomers
(27, 28) to be differentiated. LIFT-TOF spectra of [M H] ions
generated from N-acetylheparosan (29) oligosaccharides have
been shown to produce mainly C, Z, and B, Y glycosidic
cleavages with some low abundance cross-ring fragments
(Minamisawa, Suzuki, & Hirabayashi, 2006).
Mass Spectrometry Reviews DOI 10.1002/mas
9
&
HARVEY
glycans whose fragmentation spectra are recorded with a
QIT spectrometer (Ashline et al., 2005; Lapadula et al., 2005;
Zhang, Singh, & Reinhold, 2005). An algorithm named Oligosaccharide Subtree Constraint Algorithm (OSCAR) uses a database of the masses of 12,378 glycans containing hexose(0–12),
HexNAc(0–12), dHex(0–5), and Neu5Ac(0–5) and 4,542,720 possible fragments. Masses of ions from various fragmentation
pathways are used as the input and the algorithm computes and
presents the one or more structures that satisfy the fragmentation
data.
A strategy for combined MS3 and library search procedures
has been developed by Kameyama et al. (2005) for structural
analysis of N-glycans. The library consists of MS2 and MS3
spectra of all fragment ions from the MS2 spectra. In use, the
computer selects which fragment ion from the MS2 spectrum
would yield the most informative MS3 spectrum and the method
was used to assign structures to N-glycans from human IgG.
Kameyama et al. (2006) have constructed a library of
simulated fragmentation spectra in an attempt to overcome the
need for a large number of reference compounds. Di-, tri-, and
tetra-antennary N-glycans were labeled in each antenna with
13
C6-D-galactose to identify characteristic fragment patterns for
each branch type of N-linked oligosaccharides. On the basis of
the resulting characteristic fragment patterns, the authors could
simulate CID spectra for isomeric oligosaccharides and were
able to use the library to identify an N-linked glycan with
dissimilar antennae.
The biosynthetic pathways of N-linked glycans involve a
relatively small number of enzymes and monosaccharides. Many
of the enzymes can use multiple N-glycans as substrates, thus
generating a large number of glycan intermediates and making
the biosynthetic pathway resemble a network with diverging and
converging paths. Thus, the N-glycans on any one particular
glycoprotein include not only terminal glycans, but also
intermediates from the biosynthetic pathway. The program
GlycoVis has been designed to assess the glycan distribution
and potential biosynthetic route to each N-glycan taking into
account the substrate specificities of the enzymes involved. The
input to the program is the glycan distribution data and the
program outputs a reaction pathway map which labels the relative
abundance levels of different glycans with different colors. The
program also traces all possible reaction paths leading to each
glycan and identifies each pathway on the map. Use of the
program is illustrated with MALDI-TOF data from permethylated glycans from IgG and tissue plasminogen activator (TPA)
(Hossler et al., 2006).
A Glycan Finder program written in Igor Pro version 5.04B
software available from WaveMetrics, Inc., Portland, OR, for
assigning compositions to milk oligosaccharides has been
developed (Ninonuevo et al., 2006). The algorithm examines a
list of experimentally measured masses and searches for all
possible monosaccharide combinations matching the experimental mass within a specified tolerance level (mass error). In addition
to providing information regarding the possible monosaccharide
composition, the program sorts each measured mass on the basis of
its HPLC retention time and relative intensity.
An algorithm GLYCH has been developed to interpret the
high-energy MS/MS spectra of carbohydrates based on their
fragmentation spectra (Tang, Mechref, & Novotny, 2005). In
10
particular, cross-ring and internal cleavages are accommodated
to a greater extent than in other algorithms. The program first
applies a scoring scheme to identify potential bond linkages
between monosaccharides, based on the appearance pattern of
cross-ring ions. Next, it uses a dynamic programming algorithm
to determine the most probable oligosaccharide structures from
the mass spectrum and, finally, it re-evaluates these oligosaccharide structures, taking into account the double (internal)
fragmentation ions. The algorithm appears to work best for linear
structures but is still under development. A copy of the software is
available from the authors.
Lewandrowski, Resemann, and Sickmann (2005) have
shown that the high-energy CID spectra obtained with a TOF/
TOF instrument gave better scoring than spectra produced by
LID when using existing glycan databases such as GlycoSuitDB
and Glycosciences DB.
IX. STUDIES ON SPECIFIC CARBOHYDRATE TYPES
A. Polysaccharides
Most of the applications articles relating to this large group of
compounds are summarized in Tables 1–3. Only a few reports
containing information on specific methods are described below.
Analysis of most compounds by MALDI–MS is only possible
after depolymerization; methods are given in column 3 of the
tables.
Of several matrices (b-carboline, nor-harmane-DHB,
THAP and sinapinic acid) tested for UV-MALDI-TOF analysis
of b-(1 ! 3)- and b-(1 ! 4)-xylans from the red seaweed
Nothogenia fastigiata, only nor-harmane gave satisfactory
signals (positive ion mode) but with distribution profiles lower
than those determined earlier by NMR suggesting a decrease in
ionization efficiency with increasing molecular weight. Because
the glycans retain a small amount of calcium, the influence of
Ca2þ was investigated. Added sodium chloride was shown not to
change the distribution profile whereas calcium chloride suppressed the signals (Fukuyama et al., 2005). Choi and Ha (2006)
report that the relative abundance of the [M þ Na]þ ion from the
malto-oligosaccharides containing from three to seven residues
increases to a maximum for the hexamer and attribute their
findings to the increased chance for sodium bridges to form
between adjacent sugar rings for the larger oligomers.
Continuous spray deposition of aqueous solutions of
partially depolymerized methyl cellulose (30) from an HPLC
column has been reported to improve sensitivity of detection by
up to an order of magnitude compared with standard preparation
techniques (Momcilovic et al., 2005b). Furthermore, the analyte
was more evenly distributed over the target surface, resulting in
higher reproducibility. However, it provided a less accurate
estimation of average molar masses than the droplet deposition
technique. A MALDI-TOF–MS method has been developed for
Mass Spectrometry Reviews DOI 10.1002/mas
TABLE 1. Use of MALDI–MS for examination of carbohydrate oligomers and polymers from plants
(Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
&
11
HARVEY
TABLE 1. (Continued )
&
12
Mass Spectrometry Reviews DOI 10.1002/mas
&
1
Instrument type (matrix), compounds analyzed (derivatives), other techniques.
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
13
TABLE 2. Use of MALDI–MS for examination of carbohydrate polymers from bacteria
&
14
HARVEY
Mass Spectrometry Reviews DOI 10.1002/mas
&
1
Instrument type (matrix), compounds analysed (derivatives), other techniques.
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
15
&
HARVEY
TABLE 3. Use of MALDI–MS for examination of carbohydrate polymers from fungi, algae, etc.
1
Instrument type (matrix), other techniques.
the evaluation of the degree of substitution (DS) in partially
depolymerized carboxymethyl cellulose. A matrix of ammonium
sulfate and DHB gave good quality spectra without the usual
‘‘sweet-spots’’ at the crystalline rim of the MALDI target. It was
shown that the degrees of substitution calculated from spectra
acquired from the center region of the MALDI target spot
were in better agreement with those provided by the supplier
than were the values obtained from the large crystals at the
target spot rim. This observation could be one explanation for the
higher DS values reported in other publications (Enebro &
Karlsson, 2006).
A new method for structural investigations of rhamnogalacturonans involves methyl esterification of the GalA groups
with tetrabutylammonium fluoride and iodomethane in DMSO
allowing cleavage at the esterified moieties by b-elimination
at elevated temperature. Oligosaccharide fragments containing
a single side chain were generated, providing a means to
thoroughly characterize the structural features of these complex
compounds. The degree of methyl esterification was estimated by
the use of 13C-methyl groups introduced from 13C-MeI. Products
were monitored by MALDI-TOF–MS and NMR (Deng, O’Neill,
& York, 2006).
Several techniques for the analysis of xyloglucan oligosaccharides from black currents have been compared. All three
separation techniques (HPAEC, RP–HPLC, and CE) showed
different elution orders for the oligomers obtained after enzyme
degradation. HPAEC and CE showed similar separation profiles,
while RP–HPLC was not able to separate all oligomers. MALDI16
TOF–MS and ESI–MSn were also compared. They could be
used either instead of, additionally to, or coupled either off line to
HPAEC or online to RP–HPLC or CE–MS. CE with laserinduced fluorescence proved to be the fastest way to quantify
xyloglucan oligomers but MALDI-TOF–MS could be used for
fast oligosaccharide profiling, because many samples could
be analyzed in a short time. For structural characterization
ESI–MSn outclassed PSD (Hilz et al., 2006).
Oligosaccharides produced by depolymerization of hydroxypropylmethyl cellulose, hydroxypropyl cellulose or methylcellulose with endoglucanase from Bacillus agaradhaerens
have been reacted with dimethyl-, diethyl-, and dipropyl-amine
by reductive amination. All three derivatives produced a
considerable increase in sensitivity, especially for small
(DP < 3) oligosaccharides, thus partially overcoming low mass
discrimination often seen with MALDI-TOF instruments
(Momcilovic et al., 2005a). Dimethylamine was the preferred
reagent.
Chan, Chan, and Tang (2006) have compared MALDI-TOF,
direct refractometric analysis, UV–vis absorption analysis of the
Aniline Blue-stained sample and GC/MS analysis of the hydrolyzed and trimethylsilyl (TMS)-derivatized sample for estimating the molecular weight of the extracellular polysaccharide
Curdlan (4/25). All samples were fractionated by gel permeation
chromatography. Even so, the results showed that results from the
MALDI measurements underestimated the molecular weight and
polydispersity of water-insoluble Curdlan (with and without
GPC fractionation) and were unreliable.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
1. Cyclodextrins (CD) and Related Compounds
Matrix-assisted laser desorption/ionization (MALDI)-TOF and
HPLC have been used to characterize a new class of methylated
b-cyclodextrins (Jacquet et al., 2005). A thin layer of CHCA was
used as the matrix and CDs with from two to eight methyl groups
were found. The thin layer method of sample preparation was
reported to give much more reproducible spectra than targets
prepared by the dried droplet method which produced increased
signals for the more highly methylated CDs. The effect was
attributed to the properties of the analyte-matrix crystals.
The ability of cyclodextrins to form inclusion complexes has
been used by Zhang et al. (2006) to obtain molecular weights of
explosives. The inclusion complexes were produced by stirring a
mixture of the two components at 508C for 72 hr followed by
48 hr at 08C. MALDI-TOF spectra were recorded from sinapinic
acid.
Amphiphilic b-cyclodextrins with alkylthio chains at
the primary-hydroxyl side and galactosylthio-oligo-(ethylene
glycol) units at the secondary-hydroxyl side have been
synthesized and shown to form nanoparticles and vesicles
(Mazzaglia et al., 2004). These compounds were shown by
MALDI-TOF to bind to the galactose-binding lectin from
Pseudomonas aeruginosa (PA-1) which was chosen for its low
molecular weight which is only three times that of the
cyclodextrin. The spectrum of an equimolar mixture of lectin
and the cyclodextrin derivative gave peaks for the individual
constituents and the 1:1 CD:PA-1 (m/z 16,588, sodium adduct)
and 2:1 complexes showing that the binding of CD to the lectin is
relatively strong, and involves effects other than inclusion by the
CD of lectin lipophilic side chains. A MALDI mass spectrum
under the same conditions for the glucosylated CD showed a
barely detectable peak corresponding to lectin–CD complex, and
no evidence for a 1:2 complex.
2. Milk Oligosaccharides
For a recent review of milk oligosaccharides, see Mehra and
Kelly (2006). Several methods for structural determination of
human milk oligosaccharides have been compared by Ninonuevo
et al. (2006). MALDI–FTICR and IRMPD were used to analyze
HPLC fractions and another system employed a microfluidic
HPLC-Chip/MS device from Agilent, Foster City, CA. One
hundred eighty-three sugars were identified; many had large
amounts of fucose. The authors concluded that HPLC-Chip/MS
profiling of oligosaccharides provides a rapid and accurate
method for determining the number of milk oligosaccharide
components and those that contain fucosylated and sialylated
residues in the low femtomole range. The microfluidic HPLCChip/MS device was found to be both robust and to give
reproducible results.
A method has been developed for examination of milk
oligosaccharides separated on high-performance (HP) TLC
plates and applied to human and elephant milk with a limit of
detection of approximately 10 pmol (Dreisewerd et al., 2006).
Glycerol was used as a liquid matrix, to provide a homogeneous
wetting of the silica gel and an infrared laser was used for volume
material ablation and particular soft desorption/ionization conditions. ‘‘Mobility profiles’’ were acquired by scanning the laser
Mass Spectrometry Reviews DOI 10.1002/mas
&
beam across the analyte bands. A liquid composite matrix of
glycerol and the ultraviolet (UV) MALDI matrix, CHCA, allowed direct HPTLC–MALDI–MS analysis with a 337 nm-UV
laser but with a 10-fold reduction in sensitivity.
Using a library of lectins, Nakajima et al. (2006) have identified several oligosaccharides from bovine colostrum. Two
compounds that evaded identification by the lectins were
characterized as GalNAc-b-(1 ! ?)-Gal-b-(1 ! 4)-Glc, where
? represents an undetermined linkage, and GalNAc-a-(1 ! 3)(Fuc-a-(1 ! 2)-Gal-b-(1 ! 4)-Glc by MALDI–QIT-TOF–MS.
Bifidobacterium infantis has been shown to ferment purified
human milk oligosaccharides as a sole carbon source, while
another gut commensal, Lactobacillus gasseri, did not ferment
the carbohydrates (Ward et al., 2006). MALDI spectra were
recorded with an FT-ICR instrument. A unique sialylated
tetrasaccharide (GalNAc-b-(1 ! 4)-[Neu5Ac-a-(2 ! 3)]-Galb-(1 ! 4)-Glc and several other carbohydrates have been
identified in the colostrum of the bottlenose dolphin (Tursiops
truncatus) by HPLC, NMR, and MALDI–QIT–MS (DHB)
(Uemura et al., 2005). Although these glycans have not been
reported from natural sources in the free state, they are common
constituents of gangliosides.
3. Other Polysaccharides
Enzymatically digested kappa-, iota-, and hybrid iota/nu
carrageenans, sulfated polymers of 4-linked a- and b-linked
D-galactose, from red algae have been examined by MALDITOF–MS in negative mode with nor-harmane as the matrix but
loss of sulfate meant that kappa- and iota carrageenans could not
easily be distinguished from each other as they differ only in
substitution position (Antonopoulos et al., 2005). The iota/nu
carrageenans, however, could be distinguished because their
repeating units were different. For all compounds, fragmentation
involved loss of anhydrogalactose from the non-reducing end
of the molecules. Autohydrolysis products of partially cyclized
mu/nu-carrageenan from Gigartina skottsbergii, recorded by
MALDI-TOF from nor-harmane, have shown a uinmodal
distribution of even and odd peaks suggesting fragmentation of
glycosidic linkages.
B. Glycoproteins
The growing use of chromatographic and electrophoretic
methods in combination with MALDI-TOF and TOF/TOF and
on-line permethylation techniques for glycan analysis have been
reviewed (Novotny & Mechref, 2005). A large number of studies
have been published in this area; most are summarized in Tables 4
(specific glycoproteins) and 5 (whole organisms or tissues).
1. Intact Glycoproteins
Glycoproteins have been extracted from biological matrices
by use of magnetic beads coated with either Concanavalin A or
di-boronic acid. The beads were employed specifically to bind
model proteins containing N-glycans of different oligosaccharide
types. Thus, Con A beads successfully isolated RNase B from
human serum but were less efficient at isolating glycoproteins
with complex glycans. No binding of glycoproteins to the
17
TABLE 4. Use of MALDI–MS for examination of N-glycans from specific glycoproteins
&
18
HARVEY
Mass Spectrometry Reviews DOI 10.1002/mas
&
(Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
19
HARVEY
TABLE 4. (Continued )
&
20
Mass Spectrometry Reviews DOI 10.1002/mas
&
(Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
21
HARVEY
TABLE 4. (Continued )
&
22
Mass Spectrometry Reviews DOI 10.1002/mas
Mass Spectrometry Reviews DOI 10.1002/mas
Glycan release and (peptide cleavage).
Instrument (matrix), other technique, sample (derivative).
2
1
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
23
TABLE 5. Use of MALDI–MS for examination of N-glycans from intact organisms, tissues or protein mixtures
&
24
HARVEY
Mass Spectrometry Reviews DOI 10.1002/mas
Mass Spectrometry Reviews DOI 10.1002/mas
Format: Release and (peptide cleavage).
Instrument (matrix), other technique, sample (derivative).
2
1
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
25
&
HARVEY
beads was observed under competing conditions in the presence
of an excess of free mannose. Similarly, the use of di-boronic
acid-functionalized beads was validated by the capturing of
different model glycoproteins (Sparbier et al., 2005). A concanavalin A-immobilized affinity column has been developed for
glycoprotein/glycopeptide extraction and demonstrated with
ribonuclease B containing high-mannose glycans. Optimum
separation was obtained with a-methyl-D-mannopyranoside in
the mobile phase.
Müller and Allmaier (2006) have evaluated the ability of
MALDI-TOF–MS to measure the mass of intact polyclonal
human IgM which consists of a cluster of individual glycosylated
molecules. The sample was extensively desalted with a C18
ZipTip and the best MALDI matrix was found to be THAP. Ions
in charge states of 3–9 were found (Fig. 2), the possible lower
charge stated being above the mass range of the instrument. An
average mass of 1025.3 28.2 kDa was determined for the intact
molecular cluster, which turned out to be in good agreement with
published data.
2. N-Linked Glycans
Mechref, Muzikar, and Novotny (2005) have stressed the
importance of a multimethodological approach to the structural
identification of these compounds, for example, MALDI, ESI,
and FAB mass spectrometry do not provide information on
the constituent monosaccharides; such information needs to
be obtained with parallel data from exoglycosidase digestion or
GC/MS.
a. Site occupancy. One hundred seventeen hydrophobic Nglycosylated glycoproteins have been identified from extracts of
FIGURE 2. Positive ion MALDI-TOF spectrum of intact polyclonal
human IgM recorded from THAP. From Müller and Allmaier (2006) with
permission from John Wiley and Sons Ltd.
26
Caenorhabditis elegans using a proteomics approach. These
yielded 195 glycopeptides containing 199 Asn-linked glycans.
Attachment sites were identified by MALDI-TOF by utilizing the
Asn–Asp conversion after deglycosylation with PNGase F. The
glycans themselves were not identified (Fan et al., 2005b).
Similar studies using the Asn–Asp conversion has determined
that four of the six potential sites of lysosomal hydrolase
mannose 6-phosphate uncovering enzyme are glycosylated
(Wei et al., 2005b), that folate binding protein is glycosylated
at Asn-49 and -141 (Chen, Lee, & Stapels, 2006), that all three
sites (Asn-211, -262, and -303) are glycosylated in decorin from
human lung (Didraga et al., 2006b), that human recombinant
sRAGE is glycosylated at the two predicted N-glycosylation
sites, Asn-25 (completely glycosylated) and Asn-81 (partially
glycosylated) (Ostendorp et al., 2006), that five of the six
potential sites of the sGP glycoprotein of Ebola virus (Asn-40,
-204, -228, -57, and -268) are glycosylated with the remaining
one (Asn-238) being glycosylated only infrequently (Falzarano
et al., 2006) and that Asn-79, -99, and -127 from the allergens Ves
v 2 from Vespula vulgaris wasp venom are glycosylated (Skov
et al., 2006). The Asn to Asp conversion, coupled with the use of
18
O labeling and MALDI-TOF–MS was used by Tie et al. (2006)
to show that vitamin K-dependent carboxylase is N-glycosylated
at Asn-459, -605, and -627.
Okuyama et al. (2005) have determined glycosylation sites
of a-glucosidase from Schizosaccharomyses pombe by cleaving
the glycans with Endo F to leave a GlcNAc residue at the
glycosylation site and observing a 203 mass unit increment from
the mass of the tryptic or V8 peptide that contained the putative
N-glycosylation site. Glycosylation was detected at seven of
the potential 27 sites. Some information on site occupancy and
the types of glycan attached has similarly been obtained by
use of the endoglycosidase, Endo-H which also cleaves the
chitobiose core leaving the reducing terminal GlcNAc residue
attached to the protein or the peptide following tryptic digestion.
Using this approach, Liou et al. (2006) have shown that, of the
three potential glycosylation sites of NPC2, the protein
deficient in Niemann-Pick C2 disease, Asn-19 is not glycosylated, Asn-39 is linked to Endo-H-sensitive glycans whereas
Asn-116 is variably glycosylated. Similarly, Utz et al. (2006)
have used Endo-H to determine that procyclin from the protozoan
parasite Trypanosoma congolense has 13 N-linked sites; ESI MS
was used to show that these were occupied by high-mannose
glycans.
Glycosylation sites have been identified by diagonal
chromatography which involves two successive identical chromatographic steps with a chemical or enzymatic (in this case
PNGase F), step between. The different elution pattern of
the second step allows modified peptides to be identified
(Ghesquière et al., 2006). The method was demonstrated with
a1-acid glycoprotein and used to identify 117 sites in glycoproteins from depleted mouse serum.
b. N-linked glycan composition from glycopeptide analysis. A
new acid labile surfactant (RapiGest SF, sodium 3-[(2-methyl-2undecyl-1,3-dioxolan-4-yl)methoxyl]-1-propanesulfonate), produced by Waters Corporation has been introduced for denaturing
proteins prior to trypsin digestion (Yu et al., 2005b,c). It can
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
easily be degraded with acid after digestion and the products
do not interfere with subsequent MALDI analysis. Imre et al.
(2005) have shown by MALDI-TOF analysis that complete
digestion of human a1-acid glycoprotein (AGP) occurred with
RapiGest in the incubation mixture enabling very different
glycan profiles to be seen at each of the five glycosylation sites by
LC-MS/MS.
Thermal-assisted partial acid hydrolysis and TFA used to
produce glycopeptide ladders from horseradish peroxide tryptic
peptides is described in two very similar articles (Lee et al.,
2005a,c). Hydrolysis occurred mainly on the carbohydrate
portion; thus the ladders gave information on composition by
MALDI-TOF analysis. The ladders shifted to lower m/z values
with increasing reaction times. The method was later extended
to the glycoproteins ribonuclease B, avidin, human a1-acid
glycoprotein, and bovine fetuin (Lee et al., 2005b). Ladders
were obtained from ribonuclease B and avidin with one
glycosylation site but very little resolution of the hydrolysis
products could be observed from the larger glycoproteins with
several N-linked sites.
A new method based on a two-stage proteolytic digestion
has been described for characterization of glycosylated proteins
separated by gel electrophoresis (Larsen, Højrup, & Roepstorff,
2005). The first stage involved in-gel proteolysis using a
sequence-specific endoproteinase such as trypsin and a small
aliquot of the derived peptide mixture was analyzed by mass
spectrometry for protein identification based on peptide mass
mapping. The remaining peptides/glycopeptides were then incubated with a non-specific proteinase, such as proteinase K
which cleaves the majority of the tryptic peptides into smaller
peptides. The presence of a glycan created steric hindrance that
resulted in a small peptide tag attached to the glycan. Masses
were typically around 1,200 Da. Remaining peptides were
removed with a Poros R2 microcolumn packed into a GELoader
tip (glycopeptides pass through) and the glycopeptides were
trapped on a second GELoader tip microcolumn packed with
graphite powder. These glycopeptides could efficiently be
washed to remove low molecular weight contaminants and
subsequently eluted using 30% acetonitrile, 0.2% formic acid.
The method, combined with MALDI-TOF monitoring of the
glycopeptides was used to examine N-glycans from ovalbumin,
ovomucoid, and ovoglycoprotein.
Glycopeptides are often difficult to detect in the presence of
peptides; thus, when no tryptic peptides with predicted Nglycosylation sites were detected from the human CB1
cannabinoid receptor expressed in Pichia pastoris. Kim et al.
(2005b) suggested that the glycosylation sites were occupied.
Nevertheless, MALDI-TOF spectra of two glycosylated peptides
have been recorded from tryptic digests of arylphorin from the
Chinese oak silkworm (Jung, Kim, & Kim, 2005). A method for
separating sialylated tryptic glycopeptides from peptides using
capillary electrophoresis has been described (Snovida et al.,
2006a). The glycopeptides were first fractionated with a short
C18 column and then by CE with the effluent deposited directly
onto the steel MALDI target which acted as the electrode. The
technique was applied to glycopeptides from a1-acid glycoprotein and allowed the four glycosylation sites to be characterized.
Amon, Plematl, and Rizzi (2006) have developed a similar
system for deposition of the effluent from a CE column directly
Mass Spectrometry Reviews DOI 10.1002/mas
&
onto the MALDI target but, in this case, the electrode was a metal
tube surrounding the fused silica capillary with the current being
maintained through a liquid junction.
c. Glycan release. Still the most popular method of analysis of
N-glycans is to release them from the glycoprotein, either
chemically, usually with hydrazine, or enzymatically and to use
either mass spectrometry (MALDI, ESI, FAB) or HPLC after
fluorescent labeling.
i. Chemical release. Hydrazine release requires re-acetylation of the amino-sugars with acetic anhydride in the presence
of an excess of sodium hydrogen carbonate which later has to be
removed. Tanabe and Ikenaka (2006) have developed an incolumn method for hydrazine removal and re-N-acetylation
simultaneously using a single graphitic carbon column which
they claim overcomes many of the problems with the standard
method. After loading the hydrazine reaction solution, the
column was washed with 15 mL of 50 mM ammonium acetate
buffer and the glycans were eluted with 5 mL triethylamine
acetate buffer/acetonitrile (pH 7) containing 2% acetic anhydride. Yields were comparable to those of the standard method
whereas they were lower if an ammonium acetate buffer was used
for the re-N-acetylation step.
ii. Enzymatic release. Protein N-glycosidase F (PNGase F)
remains the most commonly used enzyme for glycan release,
with PNGase A being used if glycans are fucosylated at the 3position of the core GlcNAc residue. However, some glycoproteins show resistance to both enzymes as with N-glycans from
C. elegans with the unusual Gal-b-(1 ! 4)-Fuc at the 3- and 6positions. In this case, hydrazine was used instead (Hanneman
et al., 2006). Endo D from Streptococcus pneumoniae has been
reported to hydrolyze the core of complex N-glycans between
the GlcNAc residues, unlike Endo-H that preferentially hydrolyzed high-mannose structures (Yamamoto, Muramatsu, &
Muramatsu, 2005).
As an alternative to endoglycosidase release, Liu et al.
(2006a) have used pronase E at high concentration and at
extended time periods (up to 72 hr) to reduce the protein or
glycoproteins to single amino acids with only Asn attached to the
N-glycans. The resulting glycopeptides were then permethylated
under which conditions the Asn underwent b-elimination to give
a stable product. Pronase is much cheaper than PNGase, the usual
enzyme used for glycan release and the method produced
excellent results with ribonuclease B, chicken ovalbumin and
avidin. New linear glycans were also identified from Campylobacter jejuini. Another high-throughput method for release and
analysis, with full experimental details has been described by
Keck, Briggs, and Jones (2005).
In-gel methods: A method for examination of N-glycans
from plasma glycoproteins has been reported (Sagi et al., 2005),
basically following the in-gel method earlier described by Küster
et al. (1997) but with a few modifications. Clean-up of the glycans
was effected with graphatized carbon mini-cartridges rather than
with the three-bed resin technique described by Küster et al. and
the method was shown to be compatible with silver-stained
SDS–PAGE gels. Sialylated glycans were examined in linear
TOF mode to minimize observed losses of sialic acids and THAP
was shown to be the best matrix, broadly in line with previous
observations. Alternatively, the acids were stabilized by methyl
27
&
HARVEY
ester formation (Powell & Harvey, 1996). Quantitation was
initially performed by HPAEC-PAD but the glycan profiles of the
methyl esters were shown to be comparable with the exception of
the trisialo-triantennary glycan that gave a weaker signal by
MALDI analysis. The method was applied to investigations of
congenital disorders of glycosylation.
On-target methods: High-mannose glycans have been
detected and characterized from endo-polygalacturonase A from
Aspergillus niger by MALDI-TOF mass measurements before
and after on-target digestion with Endo-H and/or a-mannosidase
(Woosley et al., 2006a,b) and a MALDI-TOF profile of
glycoforms of recombinant human thyrotropin (31 kDa) has
been obtained after enzymatic desialylation on the MALDI plate
(Morelle et al., 2006b) with DHB as the matrix.
Other enzymatic release methods: Palm and Novotny (2005)
have immobilized PNGase F on a porous polymer-based
monolithic capillary column that included N-acryloxysuccinimide for enzyme immobilization. The reduced, but not alkylated,
glycoproteins, ribonuclease B, asialofetuin and ovalbumin, were
passed through the column and deglycosylation was reported to
be complete in seconds to a few minutes from 0.1 to 20 mg of
glycoprotein. The enzyme activity was reported to be reproducible for at least 8 weeks. No cleanup was needed for the
released glycans to give good signals when examined by
MALDI-TOF from DHB. Although the system worked well for
small and medium-sized glycoproteins, the authors had some
reservations about its effectiveness for larger glycoproteins.
However the possibility of direct interfacing with HPLC was
proposed.
d. N-glycan profiling. Matrix-assisted laser desorption/ionization (MALDI), with its production of only singly charged ions
from N-glycans remains the best mass spectrometric method for
glycan profiling. Although some investigators prefer ESI or LC/
MS-based methods, claiming that they provide more consistent
long-term reproducibility and are able to record spectra of
sialylated glycans, ESI spectra can present the analyst with
several problems. Frequently, multiple ions, such as [M þ H]þ
and [M þ Na]þ are produced in positive ion mode and a number
of anionic adducts, some not identified, are frequently formed
when negative ion spectra are acquired. Furthermore, ESI spectra
can also contain multiply charged ions and abundant in-source
fragments, some of which (Y-type ions) are isobaric with native
glycans. MALDI-TOF spectra of neutral glycans, on the other
hand, although often containing [M þ K]þ ions in addition to the
normal [M þ Na]þ species, are usually free of these problems
although it should be noted that acidic glycans can still present
problems as the result of in- and post-source fragmentation.
Many examples of the use of MALDI analyses are listed in
Tables 4 and 5. Following analysis by MALDI-TOF–MS, Monk
et al. (2006) have added a word of caution about the true
glycosylation of T cells when they noted that, despite stringent
washing, CD25þ and CD25 CD4þ T cells may sequester
glycans from the culture medium, thereby yielding unrepresentative N-glycan profiles and false inferences about endogenous glycosylation patterns. Some glycans appeared to originate
from glycoproteins in fetal calf serum and were absent from cells
prepared in phosphate-buffered saline (PBS). Glycans from cells
grown in serum-free media were intermediate between these two
28
examples suggesting that commercial serum-free media appears
to contain glycoproteins that are also sequestered by T cells.
Although the masses measured by MALDI analysis lead
directly to the glycan composition in terms of its monosaccharide
content, information on the nature of the monosaccharides, many
of which are isobaric, is lacking from MALDI spectra and must
be obtained by additional techniques such as exoglycosidase
sequencing. Although usually performed as a separate operation,
some investigators carry out such digestions directly on the
MALDI target. Thus, for example, Faid et al. (2006) have
performed digestions in sodium phosphate buffer and DHB
matrix. Reactions terminated by addition of the matrix.
Sulfated and phosphorylated glycans have the same nominal
mass and are not resolved with low resolution TOF instruments.
However, it has been reported that they can be differentiated by
MALDI-TOF because sulfated glycans are invariably detected as
their sodium salts (the free sulfates presumably having been
eliminated) whereas phosphates can be observed as the free acids
(Fig. 3) (Harvey & Bousfield, 2005).
e. Applications of MALDI to the detailed structural determination of N-linked glycans. Most of this work is summarized in
Tables 4 and 5 and in the section on biopharmaceuticals
(Table 16). Only work leading to the identification of some of
the more unusual glycans is reported here.
Long fucosylated poly-N-acetyllactosamine chains have been
characterized in tetra-antennary glycans of mannan-binding lectin
on the surface of human colorectal carcinoma SW1116 cells. They
were thought to be responsible for binding to microbes (Terada
et al., 2005). In-source fragmentation and MALDI-Q-TOF CID
analyses were used in their structural identification. Geyer et al.
(2005) have identified several novel N-glycans from keyhole
limpet hemocyanine in a study of cross-reactivity with glycoconjugates from Schistosoma mansoni. Most glycans were
paucimannosidic, high-mannose, or hybrid but unusual features
included one and two galactose residues attached to the a-(1 ! 6)linked core fucose (31, 32) and galactose attached directly to the
antennae-mannose residues (33). Glycans from the worm stage
of this parasite have been found to be biantennary with the
antennae consisting of repeats of GalNAc-b-(1 ! 4)[Fuc-a(1 ! 3)]GlcNAc-b(1 ! 3) (Wuhrer et al., 2006b). C. elegans has
N-glycans with Gal-b-(1 ! 4)-Fuc in both 3- and 6-positions of
the core GlcNAc (Hanneman et al., 2006), as determined by MSn
fragmentation with a MALDI-Q-TOF instrument. The glycans
also contain phosphorylcholine (3/11) substitution. MALDI-QTOF–MS/MS and PSD have shown that glycan profiles in this
species are different at each developmental stage (Cipollo et al.,
2005). Young larvae were shown to possess N-acetyllactosamine
extensions to the antennae not seen in adults. PSD analysis showed
that phosphocholine could be substituted on either core or terminally linked GlcNAc, structures not yet seen in any other organism.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
FIGURE 3. Positive ion MALDI-TOF spectra of (a) N-glycans from equine luteinizing hormone recorded
from DHB and (b) the same sample after incubation with alkaline phosphatase. Key to symbols: (&)
GlcNAc, (*) mannose, (}) galactose, ( ) fucose, (^) GalNAc. From Harvey and Bousfield (2005) with
permission from John Wiley and Sons Ltd.
Linear glycans of Glc1GalNAc5 attached to Asn by
bacillosamine (2,4-diamino-2,4,6-trideoxy-D-glucose 34) have
been identified in the bacterium Campylobacter jejuni 11168H
(Liu et al., 2006a). The enzyme PglC has been shown to be
responsible for synthesizing undecaprenyl pyrophosphate bacillosamine, an intermediate in the biosynthesis of N-linked glycans
in this bacterium (Glover et al., 2006) and the compound has been
synthesized (Weerapana et al., 2005). Sulfated high-mannose
glycans have been identified by negative ion MALDI-TOF
analysis with nor-harmane as the matrix for the first time in
Trypanosomatids; they were found in the glycoprotein crusipain
from Trypanosoma cruzi (Barboza et al., 2005). Biantennary
glycans with N-acetyllactosamine extensions to the antennae
were also found. The nematode Trichinella spiralis has been
found to synthesizes tetra-antennary glycans whose antennae are
capped with tyvelose (3,6-dideoxy-arabino-hexose, 1/15) (Bruce
& Gounaris, 2006).
f. Glycoproteomics. Uematsu et al. (2005) have developed a
deuterated reagent, caoWR, Na-((aminooxy)acetyl)tryptophanylarginine methyl ester (35) for labeling N-glycans for proteomic
studies and used it to compare glycans released from murine
Mass Spectrometry Reviews DOI 10.1002/mas
dermis and epidermis. The dermal glycans were labeled with the
2
H3 version of the derivative while the epidermal glycans
received the protonated form. High-mannose glycans were found
to be characteristic of epidermal glycoproteins.
3. O-Linked glycans
a. Determination of site occupancy. New methods for the
determination of the site of attachment of O-glycans have been
reported. Thus, a method based on the ladder sequencing
technique developed by Chait et al. (1993) has been developed
by Suzuki et al. (2006d). The glycopeptides were reacted with a
mixture of phenylisocyanate and phenylisothiocyanate and
then reacted with TFA in methanol under mild conditions
to remove the terminal residue from the phenylisothionate
derivative (the phenylisocyanate derivative was stable). The
cycle was then repeated several times to produce a ladder of
glycopeptides/peptides capped with phenylisocyanate which
29
&
HARVEY
FIGURE 4. MALDI-TOF–MS spectra of a synthetic glycopeptide after five repeated ladder sequencing
cycles under mild acid hydrolysis conditions. The ions with ~ and ^ indicate methylated ions and sodium
adduct ions, respectively. From Suzuki et al. (2006d) with permission from the American Chemical Society.
were examined by MALDI-TOF to give a spectrum from which
the peptide sequence and glycosylation could be determined
(Fig. 4).
The O-linked site of adenovirus type 5 fiber protein has been
located by a two-stage process. Proteolysis with trypsin and Glu
C localized the site to the Ile101 –Glu110 peptide and subsequent
b-elimination of the attached GlcNAc with a mixture of
2-propanol/dimethylamine/ethanethiol indicated Ser-109 as the
attachment site. The b-elimination procedure added 44 mass
units to the originally glycosylated amino acid which was
detected by MALDI-TOF–MS (Cauet et al., 2005).
b. Release of O-linked glycans. b-Elimination is still the
preferred method for releasing O-glycans. The classical
technique, involving sodium hydroxide, gives a solution from
which much sodium must be removed. A modification, using
ammonium hydroxide as the base, introduced by Huang et al.
(2002) gives a cleaner product and has been used by Steiner
et al. (2006) to release S-layer O-glycans from Geobacillus
stearothermophilus. Clean-up was with a carbon column. Taylor,
Holst, and Thomas-Oates (2006) have developed a method for
reductive b-elimination to release O-glycans from within SDS–
PAGE gels, stained either with Coomassie blue or silver. The
glycans were released with sodium borohydride and sodium
hydroxide at 508C for 16 hr before being extracted with water.
Glycans from as little as 5 mg of glycoprotein could be analyzed.
The method was developed with bovine submaxillary gland
glycoproteins and then applied to glycans from Mycobacterium
avium capsular proteins.
c. Applications of MALDI to the structural determination of
O-linked glycans. Work on this topic is mainly summarized in
Tables 6 (specific glycoproteins) and 7 (tissues and organisms).
Only a few examples of the more unusual compounds are given
here. Thus, a novel glycoprotein, named Flagellasialin, found in
30
the sperm flagella of sea urchin contains glycosylation at eight of
the possible twelve sites. The glycans consist of three a2 ! 9linked sialic acids (Neu5Ac), terminating in sulfate and attached
at the 6-position to a GalNAc residue which is attached to the
protein (Miyata et al., 2006). MALDI-TOF analysis was used
to define the glycosylation sites after desialylation. Two new
O-glycans, GalNAc and Gal-b-(1 ! 3)-GalNAc carrying 2aminoethyl-phosphate on the 6-position of the GalNAc group
have been identified in glycoproteins from the nests of the
common wasp (Vespula germanica) (Maes et al., 2005). Bovine
lens MP20 has been found to contain hexoses that are resistant to
enzymatic cleavage. Tryptic glycopeptides were examined by
MALDI-TOF/TOF–MS and their fragmentation spectra were
consistent with the presence of a hexose with a C-glycosidic link
to tryptophan (Ervin et al., 2005). Bacterial glycoproteins are
rare but MALDI-TOF–MS has assisted in the identification of
heptose residues in the autotransporter protein Ag43 from E. coli
(Sherlock et al., 2006).
i. Glycosaminoglycans (GAGS) and related compounds.
MALDI-TOF–MS has been used to determine nanogram
amounts of defined hyaluronan oligomers obtained by enzymatic
digestion of high molecular weight hyaluronan with testicular
hyaluronate lyase (Busse et al., 2006). Stronger signals were
obtained in negative ion mode than positive but the signal-tonoise (S/N) ratio in both modes was found to be a reliable
measure of the amount deposited onto the target. An amount as
low as approximately 40 fmol could be determined and there was
a linear correlation between the S/N ratio and analyte between
approximately 0.8 pmol and 40 fmol. However, the detection
limits depended considerably on the size of the oligomer with
larger oligomers being less sensitively detectable. The use of the
liquid matrices consisting of 1-methylimidazolium a-cyano-4hydroxycinnamate and butylammonium 2,5-dihydroxybenzoate
for analysis of GAGS (Laremore et al., 2006) has been mentioned
above. Other studies are summarized in Table 8.
Mass Spectrometry Reviews DOI 10.1002/mas
&
TABLE 6. Use of MALDI–MS for examination of O-glycans from specific glycopeptides
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
31
32
Instrumentation (matrix and additive).
1
TABLE 8. Use of MALDI–MS for examination of glycosaminoglycans and related compounds
Instrumentation (matrix), other techniques, sample (derivatives).
1
TABLE 7. Use of MALDI–MS for examination of O-glycans from intact organisms or tissues
&
HARVEY
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
4. GPI Anchors
A combination of hydrophilic interaction liquid chromatography
and MALDI-Q-TOF has been used to characterize glycosylphosphatidylinositol (GPI)-anchored peptides (Omaetxebarria
et al., 2006). GPI-anchor-specific diagnostic ions were observed
by MS/MS at m/z 162, 286, 422, and 447, corresponding to
glucosamine, mannose ethanolamine phosphate, glucosamine
inositol phosphate, and mannose ethanolamine phosphate glucosamine, respectively. This method was used for analysis of GPI
peptides derived from low picomole levels of the porcine kidney
membrane dipeptidase.
5. Glycoproteins and Disease
Matrix-assisted laser desorption/ionization (MALDI)–MS is
being increasingly used to detect changes in glycosylation
accompanying various disease states with the aim of identifying
possible biomarkers for disease detection and/or monitoring.
Thus, Morelle et al. (2006c) have described a method for
qualitative analysis of N-glycosylation of human serum proteins
as a method for detecting disease biomarkers. N-linked
oligosaccharides were released from patient serum glycoproteins
with PNGase F and cleaned with a graphitized carbon column.
Half of the sample was desialylated with hot acetic acid and the
other half was reacted with methyl iodide to stabilize the sialic
acids. Samples are then examined by MALDI-TOF–MS. A
parallel structural study of the released oligosaccharides involved
exoglycosidase digestions, linkage analysis, and electrospray
ionization ion trap mass spectrometry (ESI-IT-MS) of permethylated glycans. Twenty-six, mainly complex glycans were
identified. Application to patients with cirrhosis showed an
increase in bisecting N-acetylglucosamine residues and core
fucosylation.
a. Cancer. Monitoring human serum for glycoproteins that
could be used as markers for cancer has been investigated by a
number of laboratories. An et al. (2006a) have used MALDI–
FTICR–MS to look for glycans specific to ovarian cancer and
have noted at least 15 peaks in their spectra that appear to be
associated with the tumor. Several of the ions, many of which
appear to be fragments, were isolated and fragmented further
using IRMPD to determine their structure. Zhao et al. (2006)
have used lectins to monitor the distribution of a-(2 ! 3)- and
a-(2 ! 6)-linked sialic acid in serum from cancer patients and
controls. Changed glycoproteins were identified and the
glycosylation sites and glycan structures were identified by
LC-MS/MS and MALDI-TOF–MS. The method was applied to
serum from pancreatic cancer patients where Asn-83 glycosylation of a1-antitrypsin was found to be down-regulated.
Increased a-(1 ! 3)-fucosylation of complex and, in particular,
triantennary glycans (36) from a1-acid glycoprotein have been
observed in cases of inflammation and the inflammation
associated with conditions such as rheumatoid arthritis and
cancer (Higai et al., 2005). Glycopeptides were obtained by GluC digestion from the glycoprotein that had been isolated from
serum and examined by HPLC. Glycans from the five N-linked
glycosylation sites were released with PNGase F and MALDITOF analysis of desialylated glycans showed an increase in
Mass Spectrometry Reviews DOI 10.1002/mas
&
biantennary glycans and of a-(1 ! 3)-fucosylated glycans at
each site. Increased fucosylation of haptoglobin has been
identified and proposed as a biomarker for pancreatic cancer
(Okuyama et al., 2006).
Naka et al. (2006) have devised a strategy involving release
of N-glycans from cell membrane fractions, labeling with 2-AB,
fractionating according to the number of sialic acids by serotonin
affinity chromatography, desialylating, further fractionating by
normal-phase HPLC and identifying the resulting glycans by
MALDI-TOF–MS. Application of the method allowed the
investigators to detect glycans with poly-N-acetyllactosamine
chains from histocytic lymphoma cells and hyperfucosylated
glycans from gastric adenocarcinoma cells. Pochec et al. (2006)
have detected increased amounts of sialylated tetra-antennary
glycans in a3b1-integrin from a human bladder carcinoma
cell line and shown that the glycoprotein exhibits significantly
higher binding than integrin from normal epithelial cells in a
ligand-binding assay. N-glycolylneuraminic (37) acid has
been identified as its 1,2-diamino-4,5-methylenedioxybenzene
(DMB, 38) derivative by MALDI-TOF–MS from ferritin
obtained from human hepatocarcinoma tissue. This acid is not
synthesized by humans and its origin from some external source
was postulated (Asakawa et al., 2006). SELDI protein chip
technology and its use in proteomic approaches to the detection
of disease biomarkers, with emphasis on cancer diagnosis has
been reviewed (Xiao et al., 2005).
b. Congenital disorders of glycosylation (CDGs). The use of
MALDI-TOF–MS for screening for CDGs has been summarized
in a review of known diseases of this type (Freeze & Aebi, 2005)
and Wada (2006) has also published a review on the use of mass
spectrometry for studying CDGs. A method for in-gel-release of
N-glycans from plasma glycoproteins from CDG patients has
been described above and applied to cases of CDG-IIx and
HEMPAS (Sagi et al., 2005).
c. Alcohol abuse. A review including the use of MALDI-TOF
for the detection of carbohydrate-deficient transferrin as a marker
of alcohol abuse has been published (Bortolotti, De Paoli,
& Tagliaro, 2006). Elevated levels of carbohydrate-deficient
transferrin have become used as a marker for prolonged overconsumption of alcohol and an immunological test kit (Axis-Shild
%CDT) is available. However results from the kit differ from
33
&
HARVEY
those obtained by HPLC. MALDI-TOF analysis of the transferrin
showed a considerable amount of tri-sialo-transferrin that was not
supposed to be present and which probably accounted for the
discrepancy between the two results (Aldén et al., 2005). A
comparison of MALDI-TOF and ESI-Q-TOF analyses for
detecting glycosylation differences of transferrin in chronic
alcohol abuse has concluded that the ESI-Q-TOF approach is
superior on account of its higher resolution (del Castillo Busto
et al., 2005). Other studies are summarized in Table 9.
34
Format: Instrument (matrix) other technique sample (derivative).
1
A review on the importance of measuring products of nonenzymatic glycation of proteins has been published (Lapolla,
Traldi, & Fedele, 2005) and the same group has published
updates on the role of mass spectrometry in the study of protein
glycation in diabetes (Lapolla et al., 2006) and related diseases
(Lapolla, Fedele, & Traldi, 2005). Although detection of advanced glycation end-products (AGE)-modified proteins is ideally
detected by MALDI-TOF–MS, detailed structural analysis is not
possible because of the broad, usually unresolved peaks. To
overcome the problem, Kislinger et al. (2005) used peptide
mapping of Glu C digestion products and have detected, for
example, methylimidazolone (39) and argpyrimidine (40)
attached to arginine and carboxyethyl (41) bound to lysine on
the peptide KVFGRCE from lysozyme when incubated with
methylglyoxyl (3/12). Other examples are given in the article.
Glycated peptides also occur naturally as the result of in vivo
proteolysis. In a study of such systems, model glycated peptides
were obtained from glycated proteins by proteinase K, endo-Lys
C or trypsin digests and examined by both MALDI-TOF and
LC/MS. Although the two techniques gave comparable results,
MALDI detected several products that were not seen by LC/MS
(Lapolla et al., 2005b). Glu C digestion and MALDI-TOF
analysis were also used by Farah et al. (2005) to show that insulin
could be glycated at two sites on exposure to glucose; the
glycated insulin was enriched with magnetic beads containing
immobilized 3-aminophenylboronic acid (42). Mennella et al.
(2006) have studied the effect of vicinal amino acids on the
reactivity of lysine towards various carbohydrates. The presence
of hydrophobic amino acids, such as Ile, Leu, and Phe strongly
increased reactivity. Contrasting results were obtained with basic
residues. The Lys–Arg dipeptide was among the most reactive
while the Lys–Lys was not. MALDI-TOF–MS was stated to be
particularly useful for product monitoring.
TABLE 9. Use of MALDI–MS for examination of glycosylation in disease
C. Glycated Proteins (Non-Enzymatic Attachment
of Sugars)
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
automatic sample spotting and applied to a group of 184
individuals. Articles relating to more biologically targeted
projects are listed in Table 10.
D. Glycolipids
1. Lipopolysaccharides (LPS)
Studies on these compounds are summarized in Table 11.
The fragmentation behavior of D-glucose- (1/4) and Dribose- (1/1) derived Amadori peptides as well as D-fructose(1/7) derived Heynes peptides have been studied by ESI- or
MALDI-CID (Frolov, Hoffmann, & Hoffmann, 2006). All three
sugar moieties displayed characteristic fragmentation patterns
which could be explained by consecutive losses of water and
formaldehyde. Glucose-derived Amadori products showed
losses of 18, 36, 54, 72, and 84 mass units whereas ions from
the D-fructose products contained an additional loss of 96 units.
Ribose-conjugated peptides lost 18, 36, and 54 units. Each
compound yielded diagnostic lysine-derived immonium ions that
were successfully used in a precursor ion scan analysis to identify
Amadori peptides in a tryptic digest of bovine serum albumin
(BSA) glycated with D-glucose on lysines 36, 160, 235, 256, 401,
and 548.
Optimization of conditions for obtaining maximum
sequence coverage of proteins for studies of various modifications such as glycation have been performed by Wa, Cerny, and
Hage (2006) with human serum albumin (HSA) as a model
protein. A mixture of CHCA and DHB was employed as the final
matrix. This matrix, when used with a tryptic digest, gave
information on only half of the peptides. However, the combined
use of three enzyme digests, trypsin, endoproteinase Lys-C, and
endoproteinase Glu-C increased this sequence coverage to
72.8%. The use of a ZipTip to fractionate peptides in these
digests increased the sequence coverage to 97.4%. By use of this
optimized procedure Lys199 was confirmed as a glycation site on
normal HSA, whereas Lys-536 and Lys-389 were identified as
additional modification sites on minimally glycated HSA.
In a study of tryptic peptides from glycated HSA, Brancia
et al. (2006) have shown that DHB is a more effective matrix than
CHCA leading to an increase in the coverage of the glycated
protein. It was found that, regardless of the high glucose
concentration employed for HSA incubation, glycation does not
go to completion. Tandem mass spectrometric data suggested
that the CID of singly charged glycated peptides leads to specific
fragmentation pathways related to the condensed glucose
molecule. The authors suggest that the specific neutral losses
derived from the activated glycated peptides can be used as a
signature for establishing the occurrence of glycation processes.
A quantitative method for measuring glycated and glutathionylated hemoglobin using linear MALDI-TOF with a
sinapinic acid matrix has been developed by Biroccio et al.
(2005) and shown to give results in good agreement with
HPLC measurements. The method was developed by the use of
Mass Spectrometry Reviews DOI 10.1002/mas
a. Intact LPS. These complex molecules often require elaborate
methods of sample preparation in order for them to produce
strong signals but, even so, spectra can only be obtained from the
smaller molecules. Larger compounds are examined after splitting into smaller fragments; usually the lipid A portion and the
repeat units of the O-chain. Because of the normally high amount
of phosphate, spectra are normally recorded in negative ion
mode from a variety of matrices although, as with other
carbohydrates, DHB appears to be the most popular. However,
Choudhury, Carlson, and Goldberg (2005) have found that the
phosphorylated oligosaccharides from P. aeruginosa serogroupO11 gave better negative ion signals from 3-AQ than from DHB.
Phosphates can be neutralized by methylation such as with
MeOH/HCl as used by Silipo et al. (2005d) in a study of
lipooligosaccharides (LOS) from Arenibacter certesii KMM
3941T.
Sturiale et al. (2005b) have optimized conditions for
obtaining strong signals from bacterial rough (R-type) LPS and
found that, in addition to [M H] ions, the spectra contained
abundant ions originating from cleavage between the Kdo moiety
and the lipid A (Fig. 5). Sample preparation involved suspending
the LPS in a mixture of methanol/water (1:1) containing 5 mM
ethylenediaminetetraacetic acid (EDTA, 43) with sonication to
aid dissolution. A few microliters of the solution was desalted on
a small piece of Parafilm1 with some grains of Dowex 50WX8200 cation-exchange beads that had been converted into the
ammonium form. 0.3 mL of this solution was transferred to the
MALDI target along with the same volume of dibasic ammonium
citrate in a thin layer with the matrix solution that consisted of
THAP (200 mg/mL) in methanol and nitrocellulose (15 mg/mL
in acetone/propanol (1:1 by volume)) mixed in a 4:1 ratio. The
method was illustrated by spectra of LPS from Shewanella
pacifica, Xanthomonas campestris, and Pseudoalteromonas
issachenkonii. A similar method for preparing the MALDI target
was used by Liparoti et al. (2006) in the first report of b-Kdo in the
inner core of LPS from Alteromonas macleodii ATCC 27126.
Procedures such as alkaline and acid hydrolysis, mild hydrazinolysis (de-O-acylation) followed by de-N-acylation with hot
KOH were used. Another first report is of the discovery of an
enzyme that hydrolyses one of the two KDO residues that are
attached to the tetra-acylated lipid A precursor of Helicobacter
pylori LPS (Stead et al., 2005).
35
&
HARVEY
TABLE 10. Use of MALDI–MS for the study of glycated proteins
36
Mass Spectrometry Reviews DOI 10.1002/mas
&
TABLE 11. Use of MALDI–MS for examination of bacterial glycolipids
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
37
HARVEY
(Continued )
&
38
Mass Spectrometry Reviews DOI 10.1002/mas
&
TABLE 11. (Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
39
HARVEY
TABLE 11. (Continued )
&
40
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
b. Lipid A. The CID fragmentation of KDO2-lipid A (44) has
been briefly reviewed (Murphy et al., 2005). A new method
for obtaining lipid A from whole bacterial cells involves
stirring the cells with isobutyric acid/ammonium hydroxide
for 2 hr at 1008C, washing the product with methanol
and extracting the lipid A with chloroform/MeOH/water
(3:1.5:0.25 by volume) (El Hamidi et al., 2005). The
method avoids the usual hot phenol extractions and produces
very little decomposition. It was applied to lipid A from
Haemophilus influenzae and Bordetella holmesii. DHB, THAP,
and ATT with ammonium citrate appear to be the preferred
matrices for these compounds but Casabuono et al.
(2006) have obtained better spectra with nor-harmane as
matrix than with DHB for studies of Lipid A from Mesorhizobium loti. Considerable heterogeneity was present in
the spectra as the result of different chain lengths of the acyl
groups
c. Medical aspects. Matrix-assisted laser desorption/ionization (MALDI)-TOF–MS has been reported to be better than
Mass Spectrometry Reviews DOI 10.1002/mas
&
some other methods for detecting subtle differences in isogenic
strains of Staphylococcus aureus differing in their resistance
to methicillin or teicoplanin. More important changes in
MALDI-TOF–MS spectra were found with strains differing in
methicillin than in teicoplanin resistance (Majcherczyk et al.,
2006).
2. Glycosphingolipids (GSL)
These compounds can be examined intact by MALDI–MS or the
sugar portion can be removed enzymatically to reduce heterogeneity caused by the lipid as exemplified by the release of
pseudo-LewisY glycolipids of S. mansoni cercaria by endoglycoceramidase II (from Rhodococcus spp.) (Meyer et al., 2005). A
semi-quantitative method for the determination of intact
glycosphingolipids using sphingosylphosphorylcholine (45) as
the internal standard and monitoring by MALDI-TOF–MS from
DHB has been developed for detecting GSLs deposited in Fabry
disease (Fujiwaki et al., 2006). It was used to study deposition of
41
&
HARVEY
FIGURE 5. Negative ion MALDI-TOF mass spectrum of native R-type LPS from Pseudoalteromonas
issachenkonii. From Sturiale et al. (2005b) with permission from John Wiley and Sons Ltd.
ceramide trihexoside (CTH, 46) in cardiac valves. Deuterated
standards for quantification of several GSLs have been
synthesized and evaluated by ESI MS (Mills et al., 2005).
Thin-layer chromatography (TLC) has been coupled
directly with a commercial orthogonal-MALDI-TOF instrument
for the analysis of gangliosides (Ivleva et al., 2005). The matrix
was sinapinic acid, spotted onto the TLC plate after development
of the plate. Application of a declustering potential during
MALDI analysis allowed control of the matrix adducts and
clusters. Stabilization of these sialylated molecules was provided by collisional cooling. Several investigators have developed
methods for stabilization of sialic acids in these compounds. A
method, reported by Dreisewerd et al. (2005) used the liquid
matrix, glycerol, with ionization involving an Er:Yag infrared
laser to provide soft ionization conditions. The ions of lower
42
internal energy produced by atmospheric pressure MALDI have
also been used to advantage to record spectra of intact gangliosides without loss of the sialic acid (Zhang et al., 2005c).
Nakamura et al. (2006) have also coupled TLC to a MALDI-QITTOF instrument and used it to record MS2 and MS3 spectra of
glycosphingolipids. Ions characteristic of both sugar and lipid
portions were obtained. The matrix, DHB, was coated onto a
target in 1:1 acetonitrile/water and spectra were recorded from
the regions that a parallel stained plate indicated contained
sample. TLC plates directly stained with primuline also yielded
spectra. Suzuki et al. (2006c) have reported that the use of lithium
adducts, increased laser power and a cooling gas flow can
increase the abundance of the fragment ions in this QIT system.
Other studies on glycosphingolipids are listed in Table 12.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
3. Mycobacterial Glycolipids
Glucose monomycolate is synthesized by mycobacteria upon
infection. Enomoto et al. (2005) have shown up-regulation of
synthesis at 308C. The compounds, with a variety of mycolic
acids from Mycobacterium smegmatis were identified by
MALDI-TOF–MS after isolation by TLC. Trehalose (3/39) is a
prerequisite for the production of mycolates that are important
constituents of mycobacterial cell walls. Corynebacterium
glutamicum, a mutant that is unable to synthesize trehalose is,
nevertheless able to synthesize mycolates when grown on other
glucose-containing oligosaccharides. The compounds, analyzed
by MALDI-TOF and NMR contained one mycolic acid
chain attached to C6 of the reducing-terminal glucose (Tropis
et al., 2005). Cord factor (trehalose-6,60 -dimycolate) from nine
species of mycobacteria has been successfully analyzed by
MALDI-TOF–MS (Fujita et al., 2005c). Spectra were very
complicated (Fig. 6) because of the heterogeneity in both mycolic
acid chains.
E. Glycosides and Other Natural Products
Much work on glycosides relies on ESI or FAB ionization with
fewer applications involving MALDI–MS. However, the technique is still valuable in this context as illustrated by the work
summarized in Tables 13 and 14.
TABLE 12. Use of MALDI–MS for examination of glycosphingolipids
X. GLYCOSYLATION AND OTHER
REACTION MECHANISMS
Mass Spectrometry Reviews DOI 10.1002/mas
Work involving glycosidases and glycosyl-transferases where
MALDI–MS has mainly been used for product characterization,
is summarized in Table 15. Freire, D’Alayer, and Bay (2006)
have reported that SELDI-TOF is a very convenient analytical
method for monitoring bioconjugation reactions. The transglycosylation reaction of GlcNAc to a recombinant mucin
protein, MUC6, catalyzed by ppGalNAc transferases were used.
XI. INDUSTRIAL APPLICATIONS
A. Biopharmaceuticals
The growing trend towards the production of biopharmaceuticals
has resulted in studies in a large range of organisms such as the
legume Medicago truncatula that has recently been proposed,
on the bases of MALDI-TOF analysis, as promising for the
production of these pharmaceuticals (Abranches et al., 2005).
Some of these organisms produce non-human glycosylation
which can be antigenic and much work has been reported on the
use of genetic engineering to remove the enzymes responsible for
biosynthesis of antigenic glycans, predominantly those containing 1 ! 2-linked xylose and a-galactose, and to introduce
enzymes that synthesize human-type glycosylation. Plant and
insect cells are frequently used as bioreactors and a review by
Harrison and Jarvis (2006) addresses N-glycosylation in
baculovirus-insect expression systems and the engineering of
43
&
HARVEY
FIGURE 6. MALDI-TOF mass spectrum of trehalose 6,60 -dimycolate, from Mycobacterium tuberculosis
H37Rv recorded from DHB. From Fujita et al. (2005c) with permission from the Society for General
Microbiology.
insect cells to produce ‘‘mammalianized’’ recombinant glycoproteins. Thus, for example, IgG1, human embryonic kidney
(HEK) cells transfected with GlcNAc-TIII produce glycans with
bisecting GlcNAc (Schuster et al., 2005). LEC10b mutant
Chinese hamster ovary (CHO) cells have been shown to be the
cell line of choice for producing recombinant glycoproteins
whose glycans contain a bisecting GlcNAc (Stanley et al., 2005).
Production of monoclonal antibodies (IgG) represents a
major investment by many biopharmaceutical companies.
Several new methods have been developed for their analysis.
Thus, Bailey et al. (2005) have described a method for rapid and
high-throughput analysis of recombinant monoclonal antibodies
(MAbs) and their post-translational modifications. MAb capture,
desalting and in situ reduction/alkylation were accomplished by
sequential adsorption of the analyte onto solid-phase beads
suspended in microtiter plate wells. The antibodies were eluted
and digested with trypsin in the presence of the acid-labile
surfactant RapiGestTM and the resulting peptides were fractionated by stepwise elution from reverse-phase pipette tips. The
fraction containing Fc N-glycopeptides was isolated and
analyzed by linear MALDI-TOF–MS. The results were in good
agreement with those obtained by normal phase HPLC analysis
of fluorophore-labeled N-glycans released by PNGase F. A
comparison of three techniques, ESIMS, MALDI-TOF–MS,
and anion-exchange chromatography with fluorescence (2-AA)
detection for quantitative analysis of the galactosylation present
on immunoglobulins has been published by Siemiatkoski et al.
(2006). A recombinant monoclonal IgG was enzymatically
modified in vitro to produce completely galactosylated and
degalactosylated forms of the immunoglobulin. Samples of
known galactosylation levels were prepared by mixing the
modified forms with the native form. Good repeatability and
linearity were demonstrated for all three assays (RSDs <1.0%,
correlation coefficients >0.99) which were evaluated in terms of
repeatability, limit of quantitation, selectivity, and linearity. The
44
MALDI-TOF assay was best at identification of afucosylated
glycoforms but was inferior to the others for analysis of sialylated
compounds. Other work on antibodies is summarized in Table 16.
Several studies on recombinant erythropoietin (EPO) have
been reported (see Table 16). EPOs from various manufacturers
differ in several respects, but predominantly in glycosylation.
All samples contain, as their major N-glycan, sialylated tetraantennary compounds. Aranesp (NESP), however, contains a
large percentage of O-acetylated sialic acids (Stübiger et al.,
2005a), unlike EPO from other sources. Stübiger et al. (2005b)
have also used MALDI-TOF–MS to study the intact molecules
and found that Aranesp has a significantly higher molecular
weight (36.6 kDa) than the other two samples (Erypo and
NeoRecormon) used in the experiment as the result of its
additional two N-glycosylation sites (Sanz-Nebot et al., 2005).
The neutral glycoforms could be resolved after desialylation and
after N-glycans had been removed, the MALDI-TOF spectra
revealed the profile of the O-glycosylated glycoproteins. Use of
an ionene-dynamically coated capillary in a CE-MS system has
separated three glycoforms of EPO; molecular weights were
verified by MALDI-TOF–MS (Yu et al., 2005a). MALDI-TOF
has also been used to differentiate rhEPO (29 kDa from Research
Diagnostics, Flanders, NJ) from darbepoietin (36 kDa, a product
from Amgen, Thousand Oaks, CA) in spiked horse plasma
(Gupta, Sage, & Singh, 2005). Four immunoassay based methods
detected both EPOs but could not differentiate them and three
also cross-reacted with equine EPO.
MALDI-TOF analysis has been used to compare five
commercial samples of prostate-specific antigen (PSA) with
certified reference material (CRM 613) from the European
Commission Community Bureau of Reference. All samples
showed a different profile but appeared relatively stable; no
evidence for the presence of degrading enzymes was found
(Satterfield & Welch, 2005). Other work on biopharmaceuticals
is summarized in Table 16.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 13. Use of MALDI–MS for examination of glycosides
Mass Spectrometry Reviews DOI 10.1002/mas
45
&
HARVEY
TABLE 13. (Continued )
B. Agriculture
1. Nodulation (NOD) Factors from Rhizobial Bacteria
The microsymbiont Rhizobium gallicum is a fast-growing
bacterium found in European, Australian, and African soils
which is able to nodulate plants of the genus Phaseolus. It
produces four extracellular signal molecules, NOD factors (3/31)
whose structures have been elucidated by FAB, LSIMS, and
MALDI-Q-TOF–MS together with GC/MS. The NOD factors
consist of a linear GlcNAc backbone with an N-methyl group on
the reducing terminal and different N-acyl substituents. The four
acyl-oligosaccharides terminate with a sulfated N-acetylglucosaminitol (Soria-Dı́az et al., 2006). Rhizobium tropici is a
nodulator of bean growing in areas characterized by highly acidic
soils. In this work, acidity was found to increases rhizobial NOD
factor production. Significant differences were observed between
the structures produced at acid and neutral pH: 52 different
molecules were produced at acid pH, 29 at neutral pH,
and only 15 are common to bacteria grown at pH 7.0 or 4.5.
Structural identification was by a combination of MALDI-TOF,
FAB, and ESI MS. The results indicate that R. tropici CIAT899
has successfully adapted to life in acidic soils and is a good
inoculant for the bean under these conditions (Morón et al.,
2005).
2. Other Studies
Hydroxyethylmethylcelluloses, prepared from cellulose by the
action of oxirane and methyl chloride are widely used in industry
as thickeners and emulsifiers. A new quantitative method for
locating the methyl and hydroxyethyl groups which overcomes
the strong discrimination of relative ion intensities caused by
46
hydroxyalkyl groups and enables quantitative determination of
the oligomer composition after random degradation for the
first time has been developed. The method involves perdeuteriomethylation; partial acid hydrolysis; reductive amination with
propylamine; and, finally, permethylation to yield completely
O- and N-alkylated, permanently charged oligosaccharides.
Although the methyl pattern can be determined by electrospray
ionization with an ion trap and MALDI-TOF–MS, only MALDITOF–MS was found to produce quantitative results (Adden et al.,
2006b). Distribution of hydroxyethyl (HE) groups matches with a
random distribution calculated from the monomer composition,
whereas the methyl pattern was heterogeneous to a different
extent (Adden et al., 2006c). A similar methylation technique has
been used to investigate hydrolysis of six methylcelluloses by an
enzyme preparation from Trichoderma longibrachiatum (Adden
et al., 2006a). Additional examples of work with large plant
polysaccharides are included in Table 1.
XII. CARBOHYDRATE SYNTHESIS
Reviews published during the review period include those on
enzymatic polymerization of polysaccharides (Kobayashi &
Ohmae, 2006), glycopeptide synthesis (Buskas, Ingale, & Boons,
2006) and protein glycosylation (Wong, 2005). Most of the
publications in this area relate to routine monitoring of reaction
products and are summarized in Tables 17–22. Articles reporting
work mainly on method development are listed in Table 17. As
mentioned in the previous review, many chemical articles ignore
details of the equipment and conditions used to obtain mass
spectra and frequently demote what minimal, but essential
information that is supplied to ‘‘supplementary information.’’
The absence of essential information, such as the matrix used
to obtain the MALDI spectra is reflected in Tables 17–21
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
(with apologies to authors from whose articles this information
has been missed). In these cases, ‘‘MALDI’’ is used for articles
omitting to cite the type of instrument used to record the
spectra.
In addition to purely chemical methods, enzymatic methods
are used extensively in this area. Shimma et al. (2006) have
immobilized 51 human glycosyltransferases to Pir proteins and
have shown that more than 75% retained their activities. The
library was used to synthesize several carbohydrates including
some complex N-linked glycans. In addition to the use of
glycosyltransferases, glycosidases can be used as transglycosidases as illustrated by work with human endo-b-N-acetylglucosaminidase HS (Endo-HS) which is able to transfer intact
N-linked glycans to various monosaccharides (Ito et al.,
2006). Endo-b-N-acetylglucosaminidase (Endo-M) from Mucor
hiemalis expressed in Candida boidinii also has transglycosylation activity and is able to transfer biantennary complex-type
glycan from egg yolk glycoproteins to p-nitrophenyl-N-acetyl-bD-glucosamine in organic solvents such as acetone, DMSO, or
methanol (Akaike & Yamanoi, 2006). Fujita and Yamamoto
(2006) have exchanged high-mannose glycans on glycoproteins
by transglycosylation by using Endo-H to remove the highmannose glycans of ribonuclease B by cleavage of the chitobiose
core and then Endo-M from M. hiemalis to add the complex
glycan. Products were monitored by MALDI-TOF–MS from
sinapinic acid.
Another method for monitoring the products of enzymatic
glycosylation reactions involves the use of sugars covalently
linked to the surface of colloidal gold nanoparticles through a
long carbon chain ending in a S–Au bond. Laser irradiation of this
bond caused rupture and release of the attached sugar. Reactions
were monitored by enzymatic glycosylation of the attached
sugars and then recording the MALDI spectra with a LIFT-TOF/
TOF system directly from the reaction mixture—no matrix was
necessary (Nagahori & Nishimura, 2006).
As with the previous reviews, the two areas that are
particularly suitable for special mention are large molecules
such as glycodendrimers and glycoprotein conjugates.
&
ESI MS. Peripheral dansyl groups have also been observed to
undergo some photodecomposition (Baytekin et al., 2006).
MALDI-TOF analysis from IAA or dithranol of disaccharides
attached to aromatic dendrimers have shown that the higher
generation dendrimers tended to aggregate into spherical
structures when cross-linked with 1,3-phenylene diisocyanate
(47), whereas smaller molecules did not (Numata, Ikeda, &
Shinkai, 2000).
A variety of scaffolds have been used to construct these
compounds as shown in Table 18. These include monosaccharides (Gao et al., 2005b; Lu, Fraser-Reid, & Gowda, 2005; Dubber
et al., 2006a; Dubber, Sperling, & Lindhorst, 2006), cyclodextrins (Carpenter & Nepogodiev, 2005; Furuike et al., 2005;
Gómez-Garcı́a et al., 2005; Hattori et al., 2006; Yamanoi et al.,
2005), calix[4]arenes (48) (ten Cate et al., 2005; Dondoni &
Marra, 2006; Hocquelet et al., 2006), carbosilanes (Matsuoka
et al., 2006), phthalocyanines (49) (Alvarez-Mico et al., 2006),
poly(amidoamine) (PAMAM) (Ibey et al., 2005; Kubler-Kielb &
Pozsgay, 2005; Mangold et al., 2005; Morgan & Cloninger, 2005;
Wolfenden & Cloninger, 2005; Wolfenden & Cloninger, 2006;
Zhu & Marchant, 2006), peptides (Hada et al., 2005; Jin et al.,
2006; Kantchev, Chang, & Chang, 2006; Sato, Hada, & Takeda,
2006), pentaerythritol (2/33) (Xue et al., 2005; Al-Mughaid &
Grindley, 2006), porphyrins (50) (Laville et al., 2006; Sol et al.,
2006), trihydroxybenzoic acid (51) (Fernandez-Megia et al.,
2006; Joosten et al., 2006), and trimesic acid (4/61) (Patel &
Lindhorst, 2006).
A. Synthesis of Multivalent Carbohydrates,
Dendrimers, and Glycoclusters
Articles reporting work on these compounds are listed in
Table 18. Self-assembly of dendrimers towards controllable
nanomaterials has been reviewed (Smith et al., 2005). MALDITOF spectra of a PAMAM G10 dendrimer has been obtained with
THAP as the matrix (Müller & Allmaier, 2006). Sample preparation involved vacuum drying to remove the methanol and the
use of TFA/MeCN as to solvent to promote charge formation
from the amine groups. Doubly (m/z 283 kDa) and triply (m/z
193 kDa) charged ions were observed, giving a mass of around
570 kDa, considerably less than that of the calculated mass of
935 kDa. The difference was attributed to incomplete synthesis
highlighting the usefulness of MALDI for analyses of this type.
Although MALDI–MS is usually regarded as the most reliable
method for characterization of dendrimers, it has now been found
that dendrimers containing sulfonamide groups at their periphery
undergo some decomposition during ionization as shown by
Mass Spectrometry Reviews DOI 10.1002/mas
B. Synthesis of Carbohydrate–Protein Conjugates
MALDI-TOF analysis, mainly in linear mode, is used extensively
to monitor the coupling of carbohydrates to proteins and, in
particular, to estimate the number of glycans attached. As
reported in the previous reviews, the use of squaric acid is a
popular method for coupling although other linkers such as adipic
acid p-nitrophenyl diesters have been used. Work in this area is
summarized in Table 19.
47
&
HARVEY
XIII. MISCELLANEOUS STUDIES
MALDI-TOF–MS has been used to analyze the species
involved in experiments to measure the binding properties of
vancomycin-type glycopeptide antibiotics using reflectomeric
interference spectroscopy (Mehlmann et al., 2005). Although
the latter technique is sensitive, it cannot determine which of
the components of a mixture have bound to the surface, a
problem that is easily solved by MALDI–MS because each
species has a unique mass. MALDI-TOF–MS has been used
to measure acid-catalyzed oligomer formation of levoglucosan (1,6-anhydro-a-D-glucose), a product of combustion
and which can be used to monitor long-range pollution
(Holmes & Petrucci, 2006). Oligomers of up to nine residues
were detected and it was proposed that they may contribute
to the humic-like substances that are thought to be formed
from atmospheric aerosols originating from biomass
burning.
Matrix-assisted laser desorption/ionization MALDI-TOF
analysis showed that the antigen recognized by Meningococcal
Group B polysaccharide monoclonal antibodies is a disaccharide
composed of two a2-8-linked sialic acids of which one contains
an N-deacyl residue (Moe, Dave, & Granoff, 2005). Alginate
oligosaccharides (AOS), prepared through enzymatic hydrolysis
of alginate polymer, linear b-(1 ! 4)-linked glycuronan composed mainly of residues of b-D-mannosyluronic acid and its C-5
48
Mass Spectrometry Reviews DOI 10.1002/mas
&
TABLE 14. Use of MALDI–MS for examination of other natural products
(Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
49
HARVEY
TABLE 14. (Continued )
&
50
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
&
51
HARVEY
TABLE 14. (Continued )
&
52
Mass Spectrometry Reviews DOI 10.1002/mas
TABLE 15. Use of MALDI to study the products of enzyme action on carbohydrates
(Continued )
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
&
53
HARVEY
TABLE 15. (Continued )
(Continued )
&
54
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
&
55
HARVEY
&
epimer, and analyzed by MALDI-TOF–MS, have been shown to
promote growth of Bifidobacteria, prebiotics that are thought to
promote health (Wang et al., 2006d). Oligosaccharides from
honey have been characterized by size-exclusion chromatography (SEC) and MALDI-TOF–MS after fractionation with
water/ethanol solutions and activated charcoal (Morales et al.,
2006). Di- and tri-saccharides were the main constituents but
constituents with degrees of polymerization to 16 were observed
by MALDI-TOF–MS.
TABLE 15. (Continued )
XIV. CONCLUSIONS
56
Although method development has slowed in recent years, the
work reported in this review has shown that applications of
MALDI–MS to carbohydrate and glycoconjugate analysis are
very much alive and growing. The technique has been applied to a
very large range of compounds allowing problems to be solved
in many diverse areas of science and commerce. Although
electrospray ionization, with its convenient coupling to instruments that provide extensive fragmentation is now possibly
more widely used, MALDI-TOF is superior in producing glycan
profiles from mixtures because of its property of producing
essentially only singly charged ions. Spectra produced by
electrospray invariably contain multiply charged ions, various
adducts and fragments that can confuse interpretation. On the
down side, however, MALDI-TOF–MS, particularly in reflectron-TOF instruments is less attractive for sialylated glycans on
account of the tendency for the sialic acid to be eliminated either
within the ion source of during the ion’s flight through the
instrument. Nevertheless, this problem can be readily overcome
by suitable derivatization.
The past two years have seen some developments in
techniques, in particular the growth of negative ion formation
from neutral glycans by use of anion adduction and specific
matrices such as nor-harmane. Fragmentation of the resulting
negative ions produces much more informative spectra than
fragmentation in positive ion mode, mainly as the result of highly
specific reaction pathways that produce mainly cross-ring
cleavage products. Similar cross-ring product ions can also be
produced using positive ions in TOF-TOF instruments that
produce high-energy collisions and the use of these instruments
also appears to be increasing. The review period has also seen
some major advances in the development of software for
carbohydrate analysis and the introduction of new databases
containing both carbohydrates and their fragment ions.
Although none of these systems is yet able to identify all
compounds, they often provide pointers that considerably aid the
manual process.
Although the collection of the increasing number of articles
in this area is becoming more time-consuming, the advent of
powerful search engines such as Google scholar considerably
aids the process by highlighting articles in some of the more
obscure journals. Publications on the use of MALDI–MS for
the analysis of carbohydrates continue to enter new areas and
some exciting developments are expected in the coming years
with the advent of new types of mass spectrometer such as
those incorporating ion mobility separation. It is intended that
Mass Spectrometry Reviews DOI 10.1002/mas
&
TABLE 16. Use of MALDI analysis to monitor N-glycosylation in biopharmaceuticals
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Mass Spectrometry Reviews DOI 10.1002/mas
57
HARVEY
TABLE 16. (Continued )
&
58
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 17. Use of MALDI–MS in the development of synthetic methods
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
59
&
HARVEY
TABLE 17. (Continued )
TABLE 18. Use of MALDI mass spectrometry for investigations of glycodendrimers
60
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 18. (Continued )
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
61
&
HARVEY
TABLE 18. (Continued )
62
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 19. Use of MALDI for the investigation of carbohydrate–protein conjugates
TABLE 20. Use of MALDI–MS for the synthesis of carbohydrates from bacteria, fungi, etc.
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
63
&
HARVEY
TABLE 20. (Continued )
64
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 21. Use of MALDI–MS for the examination of products of carbohydrate synthesis
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
65
&
HARVEY
TABLE 21. (Continued )
66
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 21. (Continued )
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
67
&
HARVEY
TABLE 21. (Continued )
68
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
&
TABLE 21. (Continued )
(Continued )
Mass Spectrometry Reviews DOI 10.1002/mas
69
&
HARVEY
TABLE 21. (Continued )
TABLE 22. Use of MALDI to study the products combinatorial experiments
70
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
these updates follow this progress at least into the immediate
future.
XV. ABBREVIATIONS
2-AA
2-AB
2-AP
3-AQ
Abe
ABEE
ACE
AGE
AGP
Ala
AMAC
anhManol
AOS
AP-MALDI
AQC
Ara
Ara4N
Arg
Asn
Asp
ATP
ATT
Bac
BSA
CALB
Can
caoWR
Car
CD
CDG
CE
Cer
CF
CFTR
CHCA
CHO
CID
CMBT
ConA
CTH
Cym
Cys
Da
DC-SIGN
DCTB
2-aminobenzoic acid
2-aminobenzamide
2-aminopyridine
3-aminoquinoline
abequose (3,6-dideoxy-D-xylo-hexose)
aminobenzoic acid ethyl ester
angiotensin I converting enzyme
advanced glycation end-products
a1-acid glycoprotein
alanine
aminoacridone
anhydromannitol
alginate oligosaccharide
atmospheric pressure MALDI
6-aminoquinolyl-N-hydroxysuccinimidyl
carbamate
arabinose
4-amino-4-deoxy-L-arabinopyranose
arginine
asparagine
aspartic acid
adenosine triphosphate
6-azo-2-thiothymine
bacillosamine (2,4-diamino-2,4,6trideoxy-D-glucose)
bovine serum albumin
Candida antarctica lipase B
canarose
Na-((aminooxy)acetyl)tryptophanylarginine
methyl ester
caryose
cyclodextrin or circular dichroism
congenital disorder of glycosylation
capillary electrophoresis
ceramide
cystic fibrosis
cystic fibrosis transmembrane conductance
regulator
a-cyano-4-hydroxycinnamic acid
Chinese hamster ovary
collision-induced dissociation
(decomposition)
5-chloro-2-mercaptobenzothiazole
concanavalin A
ceramide trihexoside
cymarose (2,6-dideoxy-3-O-methyl-ribohexose)
cysteine
Dalton
dendritic cell-specific ICAM3-grabbing
non-integrin
2-[4-tert-butylphenyl-2-methylprop-2enylidene]malonitrile
Mass Spectrometry Reviews DOI 10.1002/mas
&
DHA
dihydroxyacetophenone (2,5-dihydroxy
isomer)
DHAP
dihydroxyacetophenone
DHB
dihydroxybenzoic acid (2,5-dihydroxy
isomer unless stated otherwise)
Dig
digitoxose (2,6-dideoxy-D-ribo-hexose)
DMB
1,2-diamino-4,5-methylenedioxybenzene
DMF
dimethylformamide
DMSO
dimethylsulfoxide
DMT-MM
4-(4,6-dimethoxy-1,2,3-triazil-2-yl)-4methylmorpholinium chloride
DNA
deoxyribonucleic acid
Dol
dolichol
DP
degree of polymerization
DS
degree of substitution
EDTA
ethylenediaminetetraacetic acid
EI
electron impact
ELIZA
enzyme-linked immunoabsorbent assay
Endo-F (D, H, M) endoglycosidase-F (D, H, M)
EPO
erythropoietin
ER
endoplasmic reticulum
ESI
electrospray ionization
EtN
ethanolamine
f (as in Galf)
furanose form of sugar ring
FAB
fast atom bombardment
FAC
frontal affinity chromatography
FGF
fibroblast growth factor
Fmoc
9-fluorenylmethoxycarbonyl
Fru
fructose
FT
Fourier transform
Fuc
fucose (6-deoxygalactose)
FucNAc
N-acetylfucoseamine
GAGS
glycosaminoglycans
Gal
galactose
GalA
galacturonic acid
GalN
galactosamine
GalNA
2-amino-2-deoxy-galacturonic acid
GalNAc
N-acetylgalactosamine
GC/MS
gas chromatography/mass spectrometry
Glc
glucose
GlcA
glucuronic acid
GlcN
glucosamine
GlcNAc
N-acetylglucosamine
GlcUA
glucuronic acid
Glu
glutamic acid
Gly
glycine
GP
glycoprotein
GPI
glycosyl-phosphatidylinositol
Gro
glycerol
GSL
glycosphingolipid
HABA
2-(40 hydroxyphenyl)azobenzoic acid
HE
hydroxyethyl
HEK
human embryonic kidney
HEMPAS
hereditary erythroblastic multinuclearity
with positive acidified serum lysis test
Hep
heptose
Hex
hexose
HexA
hexuronic acid
HexNAc
N-acetylhexosamine
71
&
HARVEY
HILIC
HIQ
HIV
HPA
HPAEC
HPLC
HRP
HSA
IAA
ICAM
ICR
IdoA
IEC
IgG (or M)
Ile
INF
Ino
IR
IRMPD
ISD
IT
Kdn
Kdo
KEGG
Ko
LLac
LC
Leu
LID
LIF
LNH
LNnH
LNnT
LNT
LOS
LPS
LSIMS
LTA
Lys
Lyx
m/z
Mab (MAB)
MALDI–MS
MALS
Man
ManA
ManNAc
MS
MUC
Neu5Ac
Neu5Gc
Neu5Pr
NKT
NMR
72
hydrophilic interaction chromatography
hydroxyisoquinoline
human immunodeficiency virus
hydroxypicolinic acid
high-performance anion exchange
chromatography
high-performance liquid chromatography
Horseradish peroxidase
human serum albumin
indoleacrylic acid
intercellular adhesion molecule
ion cyclotron resonance
iduronic acid
ion-exchange chromatography
immunoglobulin G (or M)
iso-leucine
interferon
inositol
infrared
infrared multiphoton dissociation
in-source decay
ion trap
3-deoxy-D-glycero-D-galacto-non-2ulopyranosonic acid
3-deoxy-D-manno-oct-2-ulosonic acid
Kyoto Encyclopedia of Genes and Genomes
D-glycero-D-talo-oct-2-ulosonic acid
linear (as in linear-TOF)
lactose b-D-galactopyranosyl-(1!4)-Dglucose
liquid chromatography
leucine
laser-induced dissociation
laser-induced fluorescence
lacto-N-hexaose
lacto-N-neo-hexaose
lacto-N-neo-tetraose
lacto-N-tetraose
lipooligosaccharide
lipopolysaccharides
liquid secondary ion mass spectrometry
lipoteichoic acid
lysine
lyxose
mass to charge ratio
monoclonal antibody
matrix-assisted laser desorption/ionization
mass spectrometry
multi-angle light scattering detector
mannose
mannuronic acid
N-acetylmannosamine
mass spectrometry
mucin
N-acetylneuraminic (sialic) acid
N-glycolylneuraminic acid
N-propanoylneuraminic acid
natural killer T cells
nuclear magnetic resonance
NSO
Ole
mouse myeloma cell line
oleandrose (2,6-dideoxy-3-O-methyl-Larabino-hexose)
OR
optical rotation
OSCAR
oligosaccharide subtree constraint
algorithm
P (as in GlcP)
phosphate
p (as in Glcp)
pyranose form of sugar ring
PA-1
galactose-binding lectin from Pseudomonas
aeruginosa
PAD
pulsed amperometric detection
PAGE
polyacrylamide gel electrophoresis
PAMAM
poly(amidoamine)
PBS
phosphate-buffered saline
PC
phosphorylcholine
PE
phosphoethanolamine
PEG
polyethylene glycol
PIM
phosphatidyl-myo-inositol mannosides
PMP
1-phenyl-3-methyl-5-pyrazolone
PNA
p-nitroanaline
PNGase
protein-N-glycosidase
Pro
proline
PSA
prostate-specific antigen
PSD
post-source decay
Pse
pseudaminic acid (5,7-diamino-3,5,7,9tetradeoxy-L-glycero-L-manno-non-2ulosonic acid)
PseNAc
N-acetylpseudaminic acid
Q
quadrupole
QIT
quadrupole ion trap
Qui
quinovose (6-deoxyglucose)
QuiNAc
N-acetylquinovosamine
Rreflectron (as in R-TOF)
RAGE
receptor for advanced glycation endproducts
Rha
rhamnose (6-deoxymannose)
Rib
ribose
RNA
ribonucleic acid
RNase
ribonuclease
RP
reversed phase
rPA
Bacillus anthracis protective antigen
RSD
relative standard deviation
S/N
signal-to-noise ratio
SA
sinapinic acid
SAT
sialic acid transporter
sDHB
super-DHB
SDS
sodium dodecyl sulfate
SEC
size-exclusion chromatography
SELDI
surface-enhanced laser desorption/
ionization
Ser
serine
-T (as GlcNAc-T) transferase
TEV
tobacco etch virus
TFA
trifluoroacetic acid
THAP
trihydroxyacetophenone (normally the
2,4,6-trihydroxy isomer)
The
thevetose
Thr
threonine
TLC
thin-layer chromatography
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
TMS
TOF
TPA
TT
Tyv
UDP
UV
WGA
Xyl
trimethylsilyl
time-of-flight
tissue plasminogen activator
tetanus toxoid
tyvelose (3,6-dideoxy-D-arabino-hexose)
uridine diphosph(ate)(o)
ultraviolet
wheat germ agglutinin
xylose
REFERENCES
Abe S, Moriyama H, Niikura K, Feng F, Monde K, Nishimura S-I. 2005.
Versatile synthesis of oligosaccharide-containing fullerenes. Tetrahedron Asym 16:15–19.
Abranches R, Marcel S, Arcalis E, Altmann F, Fevereiro P, Stoger E. 2005.
Plants as bioreactors: A comparative study suggests that Medicago
truncatula is a promising production system. J Biotechnol 120:121–
134.
Adden R, Melander C, Brinkmalm G, Gorton L, Mischnick P. 2006a. New
approaches to the analysis of enzymatically hydrolyzed methyl
cellulose. Part 1. Investigation of the influence of structural parameters
on the extent of degradation. Biomacromolecules 7:1399–1409.
Adden R, Muller R, Brinkmalm G, Ehrler R, Mischnick P. 2006b.
Comprehensive analysis of the substituent distribution in hydroxyethyl
celluloses by quantitative MALDI-ToF-MS. Macromol Biosci 6:435–
444.
Adden R, Niedner W, Müller R, Mischnick P. 2006c. Comprehensive analysis
of the substituent distribution in the glucosyl units and along the
polymer chain of hydroxyethylmethyl celluloses and statistical
evaluation. Anal Chem 78:1146–1157.
Adinolfi M, Galletti P, Giacomini D, Iadonisi A, Quintavalla A, Ravidà A.
2006. Toward novel glyconjugates: Efficient synthesis of glycosylated
4-alkylidene-b-lactams. Eur J Org Chem:69–73.
Aime S, Gianolio E, Palmisano G, Robaldo B, Barge A, Boffa L, Cravotto G.
2006. Improved syntheses of bis(b-cyclodextrin) derivatives, new
carriers for gadolinium complexes. Org Biomol Chem 4:1124–1130.
Aitken A. 2005. Identification of posttranslational modification by mass
spectrometry. In: Walker JM, editor. The Proteomics Protocols
Handbook. Totowa, NJ: Humana Press. pp 431–438.
Akaike E, Yamanoi T. 2006. The transglycosylation activity of the
recombinant endo-b-N-acetylglucosaminidase from Mucor hiemalis
in media containing organic solvents. Trends Glycosci Glycotechnol
18:63–71.
Akama TO, Nakagawa H, Wong NK, Sutton-Smith M, Dell A, Morris HR,
Nakayama J, Nishimura S-I, Pai A, Moremen KW, Marth JD, Fukuda
MN. 2006. Essential and mutually compensatory roles of a-mannosidase II and a-mannosidase IIx in N-glycan processing in vivo in mice.
Proc Natl Acad Sci USA 103:8983–8988.
Akamatsu M, Fujimoto Y, Kataoka M, Suda Y, Kusumoto S, Fukase K. 2006.
Synthesis of lipid A monosaccharide analogues containing acidic amino
acid: Exploring the structural basis for the endotoxic and antagonistic
activities. Bioorg Med Chem 14:6759–6777.
Aldén A, Ohlson S, Påhlsson P, Rydén I. 2005. HPLC analysis of
carbohydrate deficient transferrin isoforms isolated by the Axis-Shield
%CDT method. Clin Chim Acta 356:143–146.
Alderwick LJ, Radmacher E, Seidel M, Gande R, Hitchen PG, Morris HR,
Dell A, Sahm H, Eggeling L, Besra GS. 2005. Deletion of Cg-emb
in Corynebacterianeae leads to a novel truncated cell wall arabinogalactan, whereas inactivation of Cg-ubiA results in an arabinan-deficient
mutant with a cell wall galactan core. J Biol Chem 280:32362–32371.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Allen S, Zaleski A, Johnston JW, Gibson BW, Apicella MA. 2005. Novel
sialic acid transporter of Haemophilus influenzae. Infect Immun
73:5291–5300.
Al-Mughaid H, Grindley TB. 2006. Synthesis of a nonavalent mannoside
glycodendrimer based on pentaerythritol. J Org Chem 71:1390–1398.
Alvarez-Mico X, Calvete MJF, Hanack M, Thomas Ziegler T. 2006. The first
example of anomeric glycoconjugation to phthalocyanines. Tetrahedron Lett 47:3283–3286.
Aly MRE, Rochaix P, Amessou M, Johannes L, Florent J-C. 2006. Synthesis
of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel
electrophilic thiol-specific carbohydrate reagents. Carbohydr Res
341:2026–2036.
Aly MRE, Schmidt RR. 2005. New diacylamino protecting groups for
glucosamine. Eur J Org Chem:4382–4392.
Amin MN, Ishiwata A, Ito Y. 2006. Synthesis of asparagine-linked
bacillosamine. Carbohydr Res 341:1922–1929.
Amon S, Plematl A, Rizzi A. 2006. Capillary zone electrophoresis of
glycopeptides under controlled electroosmotic flow conditions coupled
to electrospray and matrix-assisted laser desorption/ionization mass
spectrometry. Electrophoresis 27:1209–1219.
An HJ, Lurie S, Greve LC, Rosenquist D, Kirmiz C, Labavitch JM, Lebrilla
CB. 2005a. Determination of pathogen-related enzyme action by mass
spectrometry analysis of pectin breakdown products of plant cell walls.
Anal Biochem 338:71–82.
An HJ, Ninonuevo M, Aguilan J, Liu H, Lebrilla CB, Alvarenga LS, Mannis
MJ. 2005b. Glycomics analyses of tear fluid for the diagnostic detection
of ocular rosacea. J Proteome Res 4:1981–1987.
An HJ, Miyamoto S, Lancaster KS, Kirmiz C, Li B, Lam KS, Leiserowitz GS,
Lebrilla CB. 2006a. Profiling of glycans in serum for the discovery
of potential biomarkers for ovarian cancer. J Proteome Res 5:1626–
1635.
An HJ, Tillinghast JS, Woodruff DL, Rocke DM, Lebrilla CB. 2006b. A new
computer program (GlycoX) to determine simultaneously the glycosylation sites and oligosaccharide heterogeneity of glycoproteins. J
Proteome Res 5:2800–2808.
Ando H, Shimizu H, Katano Y, Koike Y, Koizumi S, Ishida H, Kiso M. 2006.
Studies on the a-(1-4)- and a-(1-8)-fucosylation of sialic acid for the
total assembly of the glycan portions of complex HPG-series gangliosides. Carbohydr Res 341:1522–1532.
André S, Kojima S, Gundel G, Russwurm R, Schratt X, Unverzagt C, Gabius
H-J. 2006. Branching mode in complex-type triantennary N-glycans as
regulatory element of their ligand properties. Biochim Biophys Acta
1760:768–782.
Andrianasolo EH, Gross H, Goeger D, Musafija-Girt M, McPhail K, Leal RM,
Mooberry SL, Gerwick WH. 2005. Isolation of swinholide A and
related glycosylated derivatives from two field collections of marine
cyanobacteria. Org Lett 7:1375–1378.
Antonopoulos A, Hardouin J, Favetta P, Helbert W, Delmas AF, Lafosse M.
2005. Matrix-assisted laser desorption/ionisation mass spectrometry
for the direct analysis of enzymatically digested kappa- iota- and hybrid
iota/nu-carrageenans. Rapid Commun Mass Spectrom 19:2217–
2226.
Anumula KR. 2006. Advances in fluorescence derivatization methods for
high-performance liquid chromatographic analysis of glycoprotein
carbohydrates. Anal Biochem 350:1–23.
Aplander K, Tejler J, Toftered J, Carlsson S, Kahl-Knutsson B, Sundin A,
Leffler H, Nilsson UJ. 2006. Synthesis of a 30 -naphthamido-LacNAc
fluorescein conjugate with high selectivity and affinity for galectin-3.
Carbohydr Res 341:1363–1369.
Arai MA, Matsuo I, Hagihara S, Totani K, Maruyama J-I, Kitamoto K, Ito Y.
2005. Design and synthesis of oligosaccharides that interfere with
glycoprotein quality-control systems. ChemBioChem 6:2281–2289.
Arnold JN, Wallis RR, Willis AC, Harvey DJ, Royle L, Dwek RA, Rudd PM,
Sim RB. 2006. Interaction of mannan binding lectin with a-2
73
&
HARVEY
macroglobulin via exposed oligomannose glycans: A conserved feature
of the thiol-ester protein family? J Biol Chem 281:6955–6963.
Arnold JN, Wormald MR, Suter DM, Radcliffe CM, Harvey DJ, Dwek RA,
Rudd PM, Sim RB. 2005. Human serum IgM glycosylation:
Identification of glycoforms that can bind to mannan-binding lectin. J
Biol Chem 280:29080–29087.
Asakawa H, Sasabe M, Miyazaki R, Matsuda H, Fukai F, Hanada K, Hirano
H, Takasaki S. 2006. The analysis of N-glycolylneuraminic acid
(NeuGc) of hepatoma tissue and K562 cell ferritins using HPLC and
mass spectrometry. Proc Jpn Acad Ser B 82:181–187.
Ashline D, Singh S, Hanneman A, Reinhold V. 2005. Congruent strategies for
carbohydrate sequencing. 1. Mining structural details by MSn. Anal
Chem 77:6250–6262.
Aumüller I, Lindhorst TK. 2006. Chromophore-supported purification in
parallel synthesis. Eur J Org Chem:1103–1108.
Avril T, North SJ, Haslam SM, Willison HJ, Crocker PR. 2006. Probing the cis
interactions of the inhibitory receptor Siglec-7 with 2,8-disialylated
ligands on natural killer cells and other leukocytes using glycan-specific
antibodies and by analysis of 2,8-sialyltransferase gene expression. J
Leukocyte Biol 80:787–796.
Badi N, Jarroux N, Guégan P. 2006. Synthesis of per-2,3-di-O-heptyl-b and gcyclodextrins: A new kind of amphiphilic molecules bearing hydrophobic parts. Tetrahedron Lett 47:8925–8927.
Baigude H, Katsuraya K, Tokunaga S, Fujiwara N, Satoyama M, Magome T,
Okuyama K, Borjihan G, Uryu T. 2005. Synthesis of an oligosaccharide-polylysine dendrimer with reducing sugar terminals leading to
acquired immunodeficiency syndrome vaccine preparation. J Polym Sci
A 43:2195–2206.
Bailey MJ, Hooker AD, Adams CS, Zhang S, James DC. 2005. A platform for
high-throughput molecular characterization of recombinant monoclonal antibodies. J Chromatogr B 826:177–187.
Bakker H, Rouwendal GJA, Karnoup AS, Florack DEA, Stoopen GM,
Helsper JPFG, Van Ree R, Van Die I, Bosch D. 2006. An antibody
produced in tobacco expressing a hybrid b-1,4-galactosyltransferase is
essentially devoid of plant carbohydrate epitopes. Proc Natl Acad Sci
USA 103:7577–7582.
Baldwin MA. 2005. Analysis of glycosylphosphatidylinositol protein
anchors: The prion protein. Methods Enzymol 405:172–187.
Balen B, Krsnik-Rasol M, Zamfir AD, Miloševic J, Vakhrushev SY, PeterKatalinic J. 2006. Glycoproteomic survey of Mammillaria gracillis
tissues grown in vitro. J Proteome Res 5:1658–1666.
Bao X, Muramatsu T, Sugahara K. 2005. Demonstration of the pleiotrophinbinding oligosaccharide sequences isolated from chondroitin sulfate/
dermatan sulfate hybrid chains of embryonic pig brains. J Biol Chem
280:35318–35328.
Bao X, Nishimura S, Mikami T, Yamada S, Itoh N, Sugahara K. 2004.
Chondroitin sulfate/dermatan sulfate hybrid chains from embryonic pig
brain, which contain a higher proportion of L-iduronic acid than those
from adult pig brain, exhibit neuritogenic and growth factor binding
activities. J Biol Chem 279:9765–9776.
Bao X, Pavão MSG, Cabral dos Santos J, Sugahara K. 2005. A functional
dermatan sulfate epitope containing iduronate(2-O-sulfate)a1-3GalNAc(6-O-sulfate) disaccharide in the mouse brain. Demonstration
using a novel monoclonal antibody raised against dermatan sulfate of
ascidian Ascidia nigra. J Biol Chem 280:23184–23193.
Barboza M, Duschak VG, Fukuyama Y, Nonami H, Erra-Balsells R, Cazzulo
JJ, Couto AS. 2005. Structural analysis of the N-glycans of the
major cysteine proteinase of Trypanosoma cruzi. FEBS J 272:3803–
3815.
Bardor M, Cabrera G, Rudd PM, Dwek RA, Cremata JA, Lerouge P. 2006.
Analytical strategies to investigate plant N-glycan profiles in the context
of plant-made pharmaceuticals. Curr Opin Struct Biol 16:576–583.
Barton CJ, Tailford LE, Welchman H, Zhang Z, Gilbert HJ, Dupree P, Goubet
F. 2006. Enzymatic fingerprinting of Arabidopsis pectic polysacchar-
74
ides using polysaccharide analysis by carbohydrate gel electrophoresis.
Planta 224:163–174.
Bastida A, Hidalgo A, Chiara JL, Torrado M, Corzana F, Pérez-Cañadillas
JM, Groves P, Garcia-Junceda E, Gonzalez C, Jimenez-Barbero J,
Asensio JL. 2006. Exploring the use of conformationally locked
aminoglycosides as a new strategy to overcome bacterial resistance. J
Am Chem Soc 128:100–116.
Bauer J, Brandenburg K, Zähringer U, Rademann J. 2006. Chemical synthesis
of a glycolipid library by a solid-phase strategy allows elucidation of the
structural specificity of immunostimulation by rhamnolipids. Chem Eur
J 12:7116–7124.
Bauer S, Vasu P, Mort AJ, Somerville CR. 2005. Cloning, expression, and
characterization of an oligoxyloglucan reducing end-specific xyloglucanobiohydrolase from Aspergillus nidulans. Carbohydr Res 340:
2590–2597.
Baytekin B, Werner N, Luppertz F, Engeser M, Bruggemann J, Bitter S,
Henkel R, Felder T, Schalley CA. 2006. How useful is mass
spectrometry for the characterization of dendrimers? Int J Mass
Spectrom 249–250:138–148.
Bazin HG, Bess LS, Livesay MT, Ryter KT, Johnson CL, Arnold JS, Johnson
DA. 2006. New synthesis of glycolipid immunostimulants RC-529 and
CRX-524. Tetrahedron Lett 47:2087–2092.
Beck A, Bussat M-C, Zorn N, Robillard V, Klinguer-Hamour C, Chenu S,
Goetsch L, Corvaı̈a N, Van Dorsselaer A, Haeuw J-F. 2005. Characterization by liquid chromatography combined with mass spectrometry of
monoclonal anti-IGF-1 receptor antibodies produced in CHO and NS0
cells. J Chromatogr B 819:203–218.
Bedini E, Carabellese A, Comegna D, De Castro C, Parrilli M. 2006.
Synthetic oligorhamnans related to the most common O-chain
backbone from phytopathogenic bacteria. Tetrahedron 62:8474–
8483.
Bekesová S, Kovácik V, Chmelik J, Kovác P. 2006. Negative electrospray, ion
trap multistage mass spectrometry of synthetic fragments of the O-PS of
Vibrio cholerae O:1. Eur J Mass Spectrom 12:43–50.
Belgacem O, Bowdler A, Brookhouse I, Brancia FL, Raptakis E. 2006.
Dissociation of biomolecules using a ultraviolet matrix-assisted laser
desorption/ionisation time-of-flight/curved field reflectron tandem
mass spectrometer equipped with a differential-pumped collision cell.
Rapid Commun Mass Spectrom 20:1653–1660.
Bélot F, Guerreiro C, Baleux F, Mulard LA. 2005. Synthesis of two linear
PADRE conjugates bearing a deca- or pentadecasaccharide B epitope as
potential synthetic vaccines against Shigella flexneri serotype 2a
infection. Chem Eur J 11:1625–1635.
Bencúr P, Steinkellner H, Svoboda B, Mucha J, Strasser R, Kolarich D, Hann
S, Köllensperger G, Glössl J, Altmann F, Mach L. 2005. Arabidopsis
thaliana b1,2-xylosyltransferase: An unusual glycosyltransferase with
the potential to act at multiple stages of the plant N-glycosylation
pathway. Biochem J 388:515–525.
Bera A, Herbert S, Jakob A, Vollmer W, Götz F. 2005. Why are pathogenic
staphylococci so lysozyme resistant? The peptidoglycan O-acetyltransferase OatA is the major determinant for lysozyme resistance of
Staphylococcus aureus. Mol Microbiol 55:778–787.
Berenson CS, Sayles KB, Huang J, Reinhold VN, Garlipp MA, Yohe HC.
2005. Nontypeable Haemophilus influenzae-binding gangliosides of
human respiratory (HEp-2) cells have a requisite lacto/neolacto core
structure. FEMS Immunol Med Microbiol 45:171–182.
Beyer M, Koch H, Fischer K. 2006. Role of hemicelluloses in the formation of
chromophores during heat treatment of bleached chemical pulps.
Macromol Symp 232:98–106.
Bianchi A, Ferrario D, Bernardi A. 2006. A facile stereoselective synthesis of
a-glycosyl ureas. Carbohydr Res 341:1438–1446.
Bianchi A, Russo A, Bernardi A. 2005. Neo-glycoconjugates: Stereoselective
synthesis of a-glycosyl amides via Staudinger ligation reactions.
Tetrahedron Asym 16:381–386.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Bidasee KR, Zhang Y, Shao CH, Wang M, Patel KP, Dincer ÜD, Besch HRJ.
2004. Diabetes increases formation of advanced glycation end products
on sarco(endo)plasmic reticulum Ca2þ-ATPase. Diabetes 53:463–
473.
Bindschädler P, Noti C, Castagnetti E, Seeberger PH. 2006. Synthesis of a
potential 10E4 tetrasaccharide antigen involved in scrapie pathogenesis. Helv Chim Acta 89:2591–2610.
Biroccio A, Urbani A, Massoud R, di Ilio C, Sacchetta P, Bernardini S,
Cortese C, Federici G. 2005. A quantitative method for the analysis of
glycated and glutathionylated hemoglobin by matrix-assisted laser
desorption ionization-time of flight mass spectrometry. Anal Biochem
336:279–288.
Bisht KS, Bhatt S, Muppalla K. 2006. Synthesis of glycolipid analogs via
highly regioselective macrolactonization catalyzed by lipase. Tetrahedron Lett 47:8645–8649.
Biskup MB, Müller JU, Weingart R, Schmidt RR. 2005. New methods for the
generation of carbohydrate arrays on glass slides and their evaluation.
ChemBioChem 6:1007–1015.
Black C, Poile C, Langley J, Herniman J. 2006. The use of pencil lead as a
matrix and calibrant for matrix-assisted laser desorption/ionisation.
Rapid Commun Mass Spectrom 20:1053–1060.
Blattner R, Furneaux RH, Ludewig M. 2006. Syntheses of oligomannosides
in solution and on a soluble polymer support: A comparison. Carbohydr
Res 341:299–321.
Blixt O, Vasiliu D, Allin K, Jacobsen N, Warnock D, Razi N, Paulson JC,
Bernatchez S, Gilbert M, Wakarchu W. 2005. Chemoenzymatic
synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2,
GD2, GT2, GM1, and GD1a. Carbohydr Res 340:1963–1972.
Blundell CD, Almond A. 2006. Enzymatic and chemical methods for the
generation of pure hyaluronan oligosaccharides with both odd and even
numbers of monosaccharide units. Anal Biochem 353:236–247.
Bodine KD, Gin DY, Gin MS. 2005. Highly convergent synthesis of C3- or
C2-symmetric carbohydrate macrocycles. Org Lett 7:4479–4482.
Bohn ML, Colombo MI, Stortz CA, Rúveda EA. 2006. A comparative study
of the influence of some protecting groups on the reactivity of Dglucosamine acceptors with a galactofuranosyl donor. Carbohydr Res
341:1096–1104.
Bollati-Fogolı́n M, Forno G, Nimtz M, Conradt H, Etcheverrigaray M, Kratje
R. 2005. Temperature reduction in cultures of hGM-CSF-expressing
CHO cells: Effect on productivity and product quality. Biotechnol Prog
21:17–21.
Bondili JS, Castilho A, Mach L, Glössl J, Steinkellner H, Altmann F, Strasser
R. 2006. Molecular cloning and heterologous expression of b1,2xylosyltransferase and core a1,3-fucosyltransferase from maize.
Phytochemistry 67:2215–2224.
Bortolotti F, De Paoli G, Tagliaro F. 2006. Carbohydrate-deficient transferrin
(CDT) as a marker of alcohol abuse: A critical review of the literature
2001–2005. J Chromatogr B 841:96–109.
Bösch A, Nimtz M, Mischnick P. 2006. Mechanistic studies on cationic ringopening polymerisation of cyclodextrin derivatives using various Lewis
acids. Cellulose 13:493–507.
Bouillon C, Meyer A, Vidal S, Jochum A, Chevolot Y, Cloarec J-P, Praly J-P,
Vasseur J-J, Morvan F. 2006. Microwave assisted ‘‘click’’ chemistry for
the synthesis of multiple labeled-carbohydrate oligonucleotides on
solid support. J Org Chem 71:4700–4702.
Brancia FL, Bereszczak JZ, Lapolla A, Fedele D, Baccarin L, Seraglia R,
Traldi P. 2006. Comprehensive analysis of glycated human serum
albumin tryptic peptides by off-line liquid chromatography followed by
MALDI analysis on a time-of-flight/curved field reflectron tandem mass
spectrometer. J Mass Spectrom 41:1179–1185.
Brecker L, Wicklein D, Moll H, Fuchs EC, Becker W-M, Petersen A. 2005.
Structural and immunological properties of arabinogalactan polysaccharides from pollen of timothy grass (Phleum pratense L.). Carbohydr
Res 340:657–663.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Brik A, Ficht S, Yang Y-Y, Bennett CS, Wong C-H. 2006a. Sugar-assisted
ligation of N-linked glycopeptides with broad sequence tolerance at the
ligation junction. J Am Chem Soc 128:15026–15033.
Brik A, Yang Y-Y, Ficht S, Wong C-H. 2006b. Sugar-assisted glycopeptide
ligation. J Am Chem Soc 128:5626–5627.
Bruce AF, Gounaris K. 2006. Characterisation of a secreted N-acetyl-bhexosaminidase from Trichinella spiralis. Mol Biochem Parasitol
145:84–93.
Brunner A, Kolarich D, Voglmeir J, Paschinger K, Wilson IBH. 2006.
Comparative characterisation of recombinant invertebrate and vertebrate peptide O-xylosyltransferases. Glycoconj J 23:543–554.
Buchowiecka A, Bielecki S. 2003. Determination of the regiochemistry of Dglucal glucosylation by endo-b-1,3-glucanase GA Cellulomonas
cellulans using CI MS. Biocatal Biotransform 21:1–5.
Budnik BA, Lee RS, Steen JAJ. 2006. Global methods for protein
glycosylation analysis by mass spectrometry. Biochim Biophys Acta
1764:1870–1880.
Burguiere A, Hitchen PG, Dover LG, Kremer L, Ridell M, Alexander DC, Liu
J, Morris HR, Minnikin DE, Dell A, Besra GS. 2005. LosA, a key
glycosyltransferase involved in the biosynthesis of a novel family of
glycosylated acyltrehalose lipooligosaccharides from Mycobacterium
marinum. J Biol Chem 280:42124–42133.
Buskas T, Ingale S, Boons G-J. 2006. Glycopeptides as versatile tools for
glycobiology. Glycobiology 16:113R–136R.
Buskas T, Li Y, Boons G-J. 2005. Synthesis of a dimeric Lewis antigen and the
evaluation of the epitope specificity of antibodies elicited in mice. Chem
Eur J 11:5457–5467.
Busse K, Averbeck M, Anderegg U, Arnold K, Simon JC, Schiller J. 2006.
The signal-to-noise ratio as a measure of HA oligomer concentration: A
MALDI-TOF MS study. Carbohydr Res 341:1065–1070.
Bykova NV, Rampitsch C, Krokhin O, Standing K, Ens W. 2006.
Determination and characterization of site-specific N-glycosylation
using MALDI-Qq-TOF tandem mass spectrometry: Case study with a
plant protease. Anal Chem 78:1093–1103.
Cabrera JC, Messiaen J, Cambier P, Van Cutsem P. 2006. Size, acetylation and
concentration of chitooligosaccharide elicitors determine the switch
from defence involving PAL activation to cell death and water peroxide
production in Arabidopsis cell suspensions. Physiol Plant 127:44–56.
Cabrera JC, Van Cutsem P. 2005. Preparation of chitooligosaccharides with
degree of polymerization higher than 6 by acid or enzymatic
degradation of chitosan. Biochem Eng J 25:165–172.
Cai C, Zhou K, Wu Y, Wu L. 2006. Enhanced liver targeting of 5-fluorouracil
using galactosylated human serum albumin as a carrier molecule. J
Drug Target 14:55–61.
Cai Y-Z, Xing J, Sun M, Zhan Z-Q, Corke H. 2005. Phenolic antioxidants
(hydrolyzable tannins, flavonols, and anthocyanins) identified by LCESI-MS and MALDI-QIT-TOF MS from Rosa chinensis flowers. J
Agric Food Chem 53:9940–9948.
Campa C, Coslovi A, Flamigni A, Rossi M. 2006. Overview on advances in
capillary electrophoresis-mass spectrometry of carbohydrates: A
tabulated review. Electrophoresis 27:2027–2050.
Carpenter C, Nepogodiev SA. 2005. Synthesis of a aMan(1-3)aMan(12)aMan glycocluster presented on a b-cyclodextrin scaffold. Eur J Org
Chem:3286–3296.
Carpentier M, Morelle W, Coddeville B, Pons A, Masson M, Mazurier J,
Legrand D. 2005. Nucleolin undergoes partial N- and O-glycosylations
in the extranuclear cell compartment. Biochemistry 44:5804–5815.
Casabuono AC, D’Antuono A, Sato Y, Nonami H, Ugalde R, Lepek V, ErraBalsells R, Couto AS. 2006. A matrix-assisted laser desorption/
ionization mass spectrometry approach to the lipid A from Mesorhizobium loti. Rapid Commun Mass Spectrom 20:2175–2182.
Cato D, Buskas T, Boons G-J. 2005. Highly efficient stereospecific
preparation of Tn and TF building blocks using thioglycosyl donors
and the Ph2SO/Tf2O. J Carbohydr Chem 24:503–516.
75
&
HARVEY
Cauet G, Strub J-M, Leize E, Wagner E, Van Dorsselaer A, Lusky M. 2005.
Identification of the glycosylation site of the adenovirus type 5 fiber
protein. Biochemistry 44:5453–5460.
Cavalier DM, Keegstra K. 2006. Two xyloglucan xylosyltransferases catalyze
the addition of multiple xylosyl residues to cellohexaose. J Biol Chem
281:34197–34207.
Chait BT, Wang R, Beavis RC, Kent SBH. 1993. Protein ladder sequencing.
Science 262:89–92.
Chaiyaso T, H-kittikun A, Zimmermann W. 2006. Biocatalytic acylation of
carbohydrates with fatty acids from palm fatty acid distillates. J Ind
Microbiol Biotechnol 33:338–342.
Chan T-WD, Chan PK, Tang KY. 2006. Determination of molecular weight
profile for a bioactive b-(1-3) polysaccharides (Curdlan). Anal Chim
Acta 556:226–236.
Chang R, Vo T-T, Finney NS. 2006. Synthesis of the C1-phosphonate analog
of UDP-GlcNAc. Carbohydr Res 341:1998–2004.
Chen G, Bai Q, Geng X. 2006. Preparation of a concanavalin A immobilized
affinity column and its application in the structural analysis of
ribonuclease B. Chin J Chromatogr 24:425–432.
Chen H, Yan X, Zhu P, Lin J. 2006a. Antioxidant activity and hepatoprotective
potential of agaro-oligosaccharides in vitro and in vivo. Nutr J 5:31.
Chen L, Zhao X-E, Lai D, Song Z, Kong F. 2006b. A concise and practical
synthesis of antigenic globotriose, a-D-Gal-(1-4)-b-D-Gal-(1-4)-b-DGlc. Carbohydr Res 341:1174–1180.
Chen W, Lee PJ, Stapels M. 2006. The use of mass spectrometry to determine
location and extent of N-glycosylation on folate binding protein from
bovine milk. Rapid Commun Mass Spectrom 20:313–316.
Chen X, Hu L, Su X, Kong L, Ye M, Zou H. 2006c. Separation and detection of
compounds in Honeysuckle by integration of ion-exchange chromatography fractionation with reversed-phase liquid chromatographyatmospheric pressure chemical ionization mass spectrometer and
matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analysis. J Pharm Biomed Anal 40:559–570.
Chen Y-J, Chen S-H, Chien Y-Y, Chang Y-W, Liao H-K, Chang C-Y, Jan M-D,
Wang K-T, Lin C-C. 2005a. Carbohydrate-encapsulated gold nanoparticles for rapid target-protein identification and binding-epitope
mapping. ChemBioChem 6:1169–1173.
Chen Y-L, Leguijt R, Redlich H. 2006. Propane-1,3-diyl dithioacetals of
carbohydrates; Part 7: Preparation of aminocyclitols and iminosugars
by intramolecular cyclizations of D-glucosamine propane-1,3-diyl
dithioacetal derivatives. Synthesis:2242–2250.
Chen Z, Huang J, Suurs P, Schols HA, Voragen AGJ. 2005b. Granule size
affects the acetyl substitution on amylopectin populations in potato and
sweet potato starches. Carbohydr Polym 62:333–337.
Cheshev P, Marra A, Dondoni A. 2006. Direct epoxidation of D-glucal and Dgalactal derivatives with in situ generated DMDO. Carbohydr Res
341:2714–2716.
Chevalier R, Colsch B, Afonso C, Baumann N, Tabet J-C, Mallet J-M. 2006.
Synthetic sulfated glucuronosyl paragloboside (SGPG) and its use for
the detection of autoimmune peripheral neuropathies. Tetrahedron
62:563–577.
Chinthaka SDM, Chu Y, Rannulu NS, Rodgers MT. 2006. Sodium cation
affinities of MALDI matrices determined by guided ion beam tandem
mass spectrometry: Application to benzoic acid derivatives. J Phys
Chem A 110:1426–1437.
Choi S-S, Ha S-H. 2006. Characterization of ionized maltooligosaccharides
by sodium cation in MALDI-TOFMS depending on the molecular size.
Bull Korean Chem Soc 27:1243–1245.
Choi SS, Park TH. 2006. Enhancement of sialyltransferase-catalyzed transfer
of sialic acid onto glycoprotein oligosaccharides using silkworm
hemolymph and its 30K protein. J Mol Catal B Enzym 43:128–132.
Choisnard L, Gèze A, Putaux J-L, Wong Y-S, Wouessidjew D. 2006.
Nanoparticles of b-cyclodextrin esters obtained by self-assembling of
biotransesterified b-cyclodextrins. Biomacromolecules 7:515–520.
76
Choudhury B, Carlson RW, Goldberg JB. 2005. The structure of the
lipopolysaccharide from a galU mutant of Pseudomonas aeruginosa
serogroup-O11. Carbohydr Res 340:2761–2772.
Choudhury B, Leoff C, Saile E, Wilkins P, Quinn CP, Kannenberg EL,
Carlson RW. 2006. The structure of the major cell wall polysaccharide
of Bacillus anthracis is species-specific. J Biol Chem 281:27932–
27941.
Chow LP, Chiu LL, Khoo KH, Peng HJ, Yang SY, Huang SW, Su SN. 2005.
Purification and structural analysis of the novel glycoprotein allergen
Cyn d 24, a pathogenesis-related protein PR-1, from Bermuda grass
pollen. FEBS J 272:6218–6227.
Christensen B, Nielsen MS, Haselmann KF, Petersen TE, Sorensen ES. 2005.
Post-translationally modified residues of native human osteopontin are
located in clusters: Identification of 36 phosphorylation and five Oglycosylation sites and their biological implications. Biochem J
390:285–292.
Chung S-W, Joo H-S, Jang K-S, Lee H-J, Lee S-G, Kim B-G. 2006.
Galactosylation and sialylation of terminal glycan residues of human
immunoglobulin G using bacterial glycosyltransferases with in situ
regeneration of sugar-nucleotides. Enzyme Microb Technol 39:60–66.
Cid MB, Alfonso F, Martı́n-Lomas M. 2005. A study on the influence of the
structure of the glycosyl acceptors on the stereochemistry of the
glycosylation reactions with 2-azido-2-deoxy-hexopyranosyl trichloroacetimidates. Chem Eur J 11:928–938.
Cindric M, Bindila L, Cepo T, Peter-Katalinic J. 2006. Mass spectrometrybased glycoproteomic approach involving lysine derivatization for
structural characterization of recombinant human erythropoietin.
J Proteome Res 5:3066–3076.
Cipollo JF, Awad AM, Costello CE, Hirschberg CB. 2005. N-glycans of
Caenorhabditis elegans are specific to developmental stages. J Biol
Chem 280:26063–26072.
Ciucanu I. 2006. Per-O-methylation reaction for structural analysis of
carbohydrates by mass spectrometry. Anal Chim Acta 576:147–155.
Claridge TDW, Long DD, Baker CM, Odell B, Grant GH, Edwards AA,
Tranter GE, Fleet GWJ, Smith MD. 2005. Helix-forming carbohydrate
amino acids. J Org Chem 70:2082–2090.
Comelli EM, Head SR, Gilmartin T, Whisenant T, Haslam SM, North SJ,
Wong N-K, Kudo T, Narimatsu H, Esko JD, Drickamer K, Dell A,
Paulson JC. 2006a. A focused microarray approach to functional
glycomics: Transcriptional regulation of the glycome. Glycobiology
16:117–131.
Comelli EM, Sutton-Smith M, Yan Q, Amado M, Panico M, Gilmartin T,
Whisenant T, Lanigan CM, Head SR, Goldberg D, Morris HR, Dell A,
Paulson JC. 2006b. Activation of murine CD4þ and CD8þ T
lymphocytes leads to dramatic remodeling of N-linked glycans. J
Immunol 177:2431–2440.
Córdova A, IIbrahem I, Casas J, Sundén H, Engqvist M, Reyes E. 2005.
Amino acid catalyzed neogenesis of carbohydrates: A plausible ancient
transformation. Chem Eur J 11:4772–4784.
Corsaro MM, Gambacorta A, Iadonisi A, Lanzetta R, Naldi T, Nicolaus B,
Romano I, Ummarino S, Parrilli M. 2006. Structural determination of
the O-Chain polysaccharide from the lipopolysaccharide of the
haloalkaliphilic Halomonas pantelleriensis bacterium. Eur J Org
Chem:1801–1808.
Côté GL, Sheng S. 2006. Penta-, hexa-, and heptasaccharide acceptor
products of alternansucrase. Carbohydr Res 341:2066–2072.
Cottiglia F, Bonsignore L, Casu L, Deidda D, Pompei R, Casu M, Floris C.
2005. Phenolic constituents from Ephedra nebrodensis. Nat Prod Res
19:117–123.
Cox KM, Sterling JD, Regan JT, Gasdaska JR, Frantz KK, Peele CG, Black A,
Passmore D, Moldovan-Loomis C, Srinivasan M, Cuison S, Cardarelli
PM, Dickey LF. 2006. Glycan optimization of a human monoclonal
antibody in the aquatic plant Lemna minor. Nat Biotechnol 24:1591–
1597.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Cozzolino R, Malvagna P, Spina E, Giori A, Fuzzati N, Anelli A, Garozzo
D, Impallomeni G. 2006. Structural analysis of the polysaccharides
from Echinacea angustifolia radix. Carbohydr Polym 65:263–
272.
Creaser CS, Ratcliffe L. 2006. Atmospheric pressure matrix-assisted laser
desorption/ionisation mass spectrometry: A review. Curr Anal Chem
2:9–15.
Crispin M, Harvey DJ, Chang VT, Yu C, Aricescu AR, Jones EY, Davis SJ,
Dwek RA, Rudd PM. 2006. Inhibition of hybrid- and complex-type
glycosylation reveals the presence of the GlcNAc transferase Iindependent fucosylation pathway. Glycobiology 16:748–756.
Crombez L, Marques B, Lenormand JL, Mouz N, Polack B, Trocme C,
Toussaint B. 2005. High level production of secreted proteins: Example
of the human tissue inhibitor of metalloproteinases 1. Biochem Biophys
Res Commun 337:908–915.
Cui SW. 2005. Structural analysis of polysaccharides. In: Cui SW, editor.
Food carbohydrates: Chemistry, physical properties and applications.
Baca Raton, FL: Taylor and Francis. pp 105–160.
Cumpstey I. 2006. New oligosaccharide analogues: Non-glycosidically
linked thioether-bridged pseudodisaccharides. Synlett:1711–1714.
da Silva BP, Campos PO, Parente JP. 2006. Chemical structure and biological
activity of steroidal saponins from Furcraea gigantea. Chem Nat
Compd 42:316–321.
Damager I, Jensen MT, Olsen CE, Blennow A, Møller BL, Svensson B,
Motawia MS. 2005. Chemical synthesis of a dual branched maltodecaose: A potential substrate for a-amylases. ChemBioChem 6:1224–
1233.
De Castro C, Carannante A, Lanzetta R, Liparoti V, Molinaro A, Parrilli M.
2006. Core oligosaccharide structure from the highly phytopathogenic
Agrobacterium tumefaciens TT111 and conformational analysis of the
putative rhamnan epitope. Glycobiology 16:1272–1280.
De Castro C, Molinaro A, Lanzetta R, Holst O, Parrilli M. 2005. The linkage
between O-specific caryan and core region in the lipopolysaccharide of
Burkholderia caryophylli is furnished by a primer monosaccharide.
Carbohydr Res 340:1802–1807.
de Jesús Pérez J, Juárez S, Chen D, Scott CL, Hartweck LM, Olszewski NE,
Garcı́a JA. 2006. Mapping of two O-GlcNAc modification sites in the
capsid protein of the potyvirus Plum pox virus. FEBS Lett 580:5822–
5828.
de la Salle H, Mariotti S, Angenieux C, Gilleron M, Garcia-Alles L-F,
Malm D, Berg T, Paoletti S, Maı̂tre B, Mourey L, Salamero J, Cazenave
JP, Hanau D, Mori L, Puzo G, De Libero G. 2005. Assistance of
microbial glycolipid antigen processing by CD1e. Science 310:1321–
1324.
De Lorenzo C, Cozzolino R, Carpentieri A, Pucci P, Laccetti P, D’Alessio G.
2005. Biological properties of a human compact anti-ErbB2 antibody.
Carcinogenesis 26:1890–1895.
de Paz JL, Noti C, Seeberger PH. 2006. Microarrays of synthetic heparin
oligosaccharides. J Am Chem Soc 128:2766–2767.
de Paz J-L, Ojeda R, Barrientos ÁG, Penadés S, Martı́n-Lomas M. 2005.
Synthesis of a Ley neoglycoconjugate and Ley-functionalized gold
glyconanoparticles. Tetrahedron Asym 16:149–158.
de Rijke E, Out P, Niessen WMA, Ariese F, Gooijer C, Brinkman UAT. 2006.
Analytical separation and detection methods for flavonoids. J
Chromatogr A 1112:31–63.
de Segura AG, Alcalde M, Bernabé M, Ballesteros A, Plou FJ. 2006.
Synthesis of methyl a-D-glucooligosaccharides by entrapped dextransucrase from Leuconostoc mesenteroides B-1299. J Biotechnol 124:
439–445.
DeFrees S, Wang Z-G, Xing R, Scott AE, Wang J, Zopf D, Gouty DL,
Sjoberg ER, Panneerselvam K, Brinkman-Van der Linden ECM, Bayer
RJ, Tarp MA, Clausen H. 2006. GlycoPEGylation of recombinant
therapeutic proteins produced in Escherichia coli. Glycobiology
16:833–843.
Mass Spectrometry Reviews DOI 10.1002/mas
&
del Castillo Busto ME, Montes-Bayón M, Blanco-González E, Meija J, SanzMedel A. 2005. Strategies to study human serum transferrin isoforms
using integrated liquid chromatography ICPMS, MALDI-TOF, and
ESI-Q-TOF detection: Application to chronic alcohol abuse. Anal
Chem 77:5615–5621.
Dellagreca M, Previtera L, Zarrelli A. 2005. A new xyloside from
Chenopodium album. Nat Prod Res 19:87–90.
Demelbauer UM, Plematl A, Josic D, Allmaier G, Rizzi A. 2005. On
the variation of glycosylation in human plasma derived antithrombin.
J Chromatogr A 1080:15–21.
Deng C, O’Neill MA, York WS. 2006. Selective chemical depolymerization
of rhamnogalacturonans. Carbohydr Res 341:474–484.
Deng S, Gangadharmath U, Chang C-WT. 2006. Sonochemistry: A powerful
way of enhancing the efficiency of carbohydrate synthesis. J Org Chem
71:5179–5185.
Dengjel J, Rammensee H-G, Stevanovic S. 2005. Glycan side chains on
naturally presented MHC class II ligands. J Mass Spectrom 40:100–
104.
Deshayes C, Laval F, Montrozier H, Daffé M, Etienne G, Reyrat J-M. 2005.
A glycosyltransferase involved in biosynthesis of triglycosylated
glycopeptidolipids in Mycobacterium smegmatis: Impact on surface
properties. J Bacteriol 187:7283–7291.
Devakumar A, Thompson MS, Reilly JP. 2005. Fragmentation of oligosaccharide ions with 157 nm vacuum ultraviolet light. Rapid Commun
Mass Spectrom 19:2313–2320.
Di Fabio G, Randazzo A, D’Onofrio J, Ausı́n C, Pedroso E, Grandas A, De
Napoli L, Montesarchio D. 2006. Cyclic phosphate-linked oligosaccharides: Synthesis and conformational behavior of novel cyclic
oligosaccharide analogues. J Org Chem 71:3395–3408.
Di Patrizi L, Rosati F, Guerranti R, Pagani R, Gerwig GJ, Kamerling JP. 2006.
Structural characterization of the N-glycans of gpMuc from Mucuna
pruriens seeds. Glycoconj J 23:599–609.
Di Stasio B, Frochot C, Dumas E, Even P, Zwier J, Müller A, Didelon J,
Guillemin F, Viriot M-L, Barberi-Heyob M. 2005. The 2aminoglucosamide motif improves cellular uptake and photodynamic
activity of tetraphenylporphyrin. Eur J Med Chem 40:1111–1122.
Dicko MH, Hilhorst R, Traore AS. 2005. Indigenous West African plants as
novel sources of polysaccharide degrading enzymes: Application in the
reduction of the viscosity of cereal porridges. Afr J Biotechnol 4:1095–
1104.
Didraga M, Barroso B, Bischoff R. 2006. Recent developments in
proteoglycan purification and analysis. Curr Pharm Anal 2:323–337.
Didraga M, Barroso B, de Vries M, Kerstjens H, Postma D, Bischoff R. 2006.
Purification of decorin core protein from human lung tissue. J
Chromatogr A 1123:151–159.
Dignam CF, Randall LA, Blacken RD, Cunningham PR, Lester S-KG, Brown
MJ, French SC, Aniagyei SE, Wenzel TJ. 2006. Carboxymethylated
cyclodextrin derivatives as chiral NMR discriminating agents. Tetrahedron Asym 17:1199–1208.
Dinadayala P, Kaur D, Berg S, Amin AG, Vissa VD, Chatterjee D, Brennan
PJ, Crick DC. 2006. Genetic basis for the synthesis of the
immunomodulatory mannose caps of lipoarabinomannan in Mycobacterium tuberculosis. J Biol Chem 281:20027–20035.
Disney MD, Hook DF, Namoto K, Seeberger PH, Seebach D. 2005. N-linked
glycosylated b-peptides are resistant to degradation by glycoamidase A.
Chem Biodiversity 2:1624–1634.
Dmochowska B, Skorupa E, Pellowska-Januszek L, Czarkowska M, Sikorski
A, Wisniewski A. 2006. Preparation, single-crystal X-ray diffraction
and high-resolution NMR spectroscopic analyses of N-[(1,4-anhydro5-deoxy-2,3-O-isopropylidene-D,L-ribitol)-5-yl]trimethylammonium
iodide. Carbohydr Res 341:1916–1921.
Dondoni A, Catozzi N, Marra A. 2005. Concise and practical synthesis of Cglycosyl ketones from sugar benzothiazoles and their transformation
into chiral tertiary alcohols. J Org Chem 70:9257–9268.
77
&
HARVEY
Dondoni A, Marra A. 2006. C-glycoside clustering on calix[4]arene,
adamantane, and benzene scaffolds through 1,2,3-triazole linkers.
J Org Chem 71:7546–7557.
Dondoni A, Massi A, Minghini E. 2006. A facile and general entry to Cglycosyl (R)- and (S)-b-amino acid pairs from glycosyl cyanides
through enamino ester intermediates. Synlett:539–542.
Dondoni A, Nuzzi A. 2006. Access to piperidine imino-C-glycosides via
stereoselective thiazole-based aminohomologation of pyranoses. J Org
Chem 71:7574–7582.
Dreisewerd K, Kölbl S, Peter-Katalinic J, Berkenkamp S, Pohlentz G. 2006.
Analysis of native milk oligosaccharides directly from thin-layer
chromatography plates by matrix-assisted laser desorption/ionization
orthogonal-time-of-flight mass spectrometry with a glycerol matrix. J
Am Soc Mass Spectrom 17:139–150.
Dreisewerd K, Müthing J, Rohlfing A, Meisen I, Vukelic Z, Peter-Katalinic J,
Hillenkamp F, Berkenkamp S. 2005. Analysis of gangliosides directly
from thin-layer chromatography plates by infrared matrix-assisted laser
desorption/ionization orthogonal time-of-flight mass spectrometry with
a glycerol matrix. Anal Chem 77:4098–4107.
Du W, Gervay-Hague J. 2005. Efficient synthesis of a-galactosyl ceramide
analogues using glycosyl iodide donors. Org Lett 7:2063–2065.
Du Y, Wei G, Cheng S, Hua Y, Linhardt RJ. 2006. HClO4 –SiO2 catalyzed
glycosylation using sugar trichloroacetimidates as glycosyl donors.
Tetrahedron Lett 47:307–310.
Dubber M, Patel A, Sadalapure K, Aumüller I, Lindhorst TK. 2006. Synthesis
of functionalized amphiphilic glycoconjugates and glycoclusters. Eur J
Org Chem:5357–5366.
Dubber M, Sperling O, Lindhorst TK. 2006. Oligomannoside mimetics by
glycosylation of octopus glycosides and their investigation as inhibitors
of type 1 fimbriae-mediated adhesion of Escherichia coli. Org Biomol
Chem 4:3901–3912.
Duchesne L, Tissot B, Rudd TR, Dell A, Fernig DG. 2006. N-glycosylation of
fibroblast growth factor receptor 1 regulates ligand and heparan sulfate
co-receptor binding. J Biol Chem 281:27178–27189.
Duffy MS, Morris HR, Dell A, Appleton JA, Haslam SM. 2006. Protein
glycosylation in Parelaphostrongylus tenuis—First description of
the Gala1-3Gal sequence in a nematode. Glycobiology 16:854–
862.
Dumon C, Bosso C, Utille JP, Heyraud A, Samain E. 2006. Production of
Lewis x tetrasaccharides by metabolically engineered Escherichia coli.
ChemBioChem 7:359–365.
Dziadek S, Kowalczyk D, Kunz H. 2005. Synthetic vaccines consisting of
tumor-associated MUC1 glycopeptide antigens and bovine serum
albumin. Angew Chem Int Ed Engl 44:7624–7630.
Edwards KJ, Allen S, Gibson BW, Campagnari AA. 2005a. Characterization
of a cluster of three glycosyltransferase enzymes essential for
Moraxella catarrhalis lipooligosaccharide assembly. J Bacteriol
187:2939–2947.
Edwards KJ, Schwingel JM, Datta AK, Campagnari AA. 2005b. Multiplex
PCR assay that identifies the major lipooligosaccharide serotype
expressed by Moraxella catarrhalis clinical isolates. J Clin Microbiol
43:6139–6143.
Ehara K, Saka S. 2005. Decomposition behavior of cellulose in supercritical
water, subcritical water and their combined treatments. J Wood Sci
51:148–153.
El Alaoui A, Schmidt F, Monneret C, Florent J-C. 2006. Protecting groups for
glucuronic acid: Application to the synthesis of new paclitaxel (taxol)
derivatives. J Org Chem 71:9628–9636.
El Hamidi A, Tirsoaga A, Novikov A, Hussein A, Caroff M. 2005.
Microextraction of bacterial lipid A: Easy and rapid method for mass
spectrometric characterization. J Lipid Res 46:1773–1778.
Eleutério MIP, Schimmel J, Ritter G, Costa MdC, Schmidt RR. 2006.
Synthesis of saponins with allobetulin and glycyrrhetic acid as
aglycones. Eur J Org Chem:5293–5304.
78
Enebro J, Karlsson S. 2006. Improved matrix-assisted laser desorption/
ionisation time-of-flight mass spectrometry of carboxymethyl cellulose. Rapid Commun Mass Spectrom 20:3693–3698.
Engelmann K, Kinlough CL, Müller S, Razawi H, Baldus SE, Hughey RP,
Hanisch F-G. 2005. Transmembrane and secreted MUC1 probes show
trafficking-dependent changes in O-glycan core profiles. Glycobiology
15:1111–1124.
Enomoto Y, Sugita M, Matsunaga I, Naka T, Sato A, Kawashima T, Shimizu
K, Takahashi H, Norose Y, Yano I. 2005. Temperature-dependent
biosynthesis of glucose monomycolate and its recognition by CD1restricted T cells. Biochem Biophys Res Commun 337:452–456.
Erb WJ, Hanton SD, Owens KG. 2006. A study of gas-phase cationization in
matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 20:2165–2169.
Ernst RK, Adams KN, Moskowitz SM, Kraig GM, Kawasaki K, Stead CM,
Trent S, Miller SI. 2006. The Pseudomonas aeruginosa lipid A
deacylase: Selection for expression and loss within the cystic fibrosis
airway. J Bacteriol 188:191–201.
Ervin LA, Ball LE, Crouch RK, Schey KL. 2005. Phosphorylation and
glycosylation of bovine lens MP20. Invest Ophthalmol Vis Sci 46:627–
635.
Erwin AL, Allen S, Ho DK, Bonthius PJ, Jarisch J, Nelson KL, Tsao DL,
Unrath WCT, Watson MEJ, Gibson BW, Apicella MA, Smith AL. 2006.
Role of lgtC in resistance of nontypeable Haemophilus influenzae strain
R2866 to human serum. Infect Immun 74:6226–6235.
Esua MF, Rauwald J-W. 2006. Novel bioactive maloyl glucans from Aloe vera
gel: Isolation, structure elucidation and in vitro bioassays. Carbohydr
Res 341:355–364.
Ethier M, Krokhin O, Ens W, Standing KG, Wilkins JA, Perreault H. 2005.
Global and site-specific detection of human integrin a5b1 glycosylation
using tandem mass spectrometry and the StrOligo algorithm. Rapid
Commun Mass Spectrom 19:721–727.
Ethier M, Saba JA, Ens W, Standing KG, Perreault H. 2002. Automated
structural assignment of derivatized complex N-linked oligosaccharides
from tandem mass spectra. Rapid Commun Mass Spectrom 16:1743–
1754.
Ethier M, Saba JA, Spearman M, Krokhin O, Butler M, Ens W, Standing KG,
Perreault H. 2003. Application of the StrOligo algorithm for the
automated structure assignment of complex N-linked glycans from
glycoproteins using tandem mass spectrometry. Rapid Commun Mass
Spectrom 17:2713–2720.
Etienne G, Laval F, Villeneuve C, Dinadayala P, Abouwarda A, Zerbib D,
Galamba A, Daffé M. 2005. The cell envelope structure and properties
of Mycobacterium smegmatis mc2155: Is there a clue for the unique
transformability of the strain? Microbiology 151:2075–2086.
Faid V, Evjen G, Tollersrud O-K, Michalski J-C, Morelle W. 2006. Sitespecific glycosylation analysis of the bovine lysosomal a-mannosidase.
Glycobiology 16:440–461.
Faiz JA, Spencer N, Pikramenou Z. 2005. Acetylenic cyclodextrins for
multireceptor architectures: Cups with sticky ends for the formation of
extension wires and junctions. Org Biomol Chem 3:4239–4245.
Falzarano D, Krokhin O, Wahl-Jensen V, Seebach J, Wolf K, Schnittler H-J,
Feldmann H. 2006. Structure-function analysis of the soluble
glycoprotein, sGP, of ebola virus. ChemBioChem 7:1605–1611.
Fan G-T, Pan Y, Lu K-C, Cheng Y-P, Lin W-C, Lin S, Lin C-H, Wong C-H,
Fang J-M, Lin C-C. 2005a. Synthesis of a-galactosyl ceramide and the
related glycolipids for evaluation of their activities on mouse
splenocytes. Tetrahedron 61:1855–1862.
Fan X, She Y-M, Bagshaw RD, Callahan JW, Schachter H, Mahuran DJ.
2005b. Identification of the hydrophobic glycoproteins of Caenorhabditis elegans. Glycobiology 15:952–964.
Faraco V, Palmieri G, Festa G, Monti M, Sannia G, Giardina P. 2005. A new
subfamily of fungal subtilases: Structural and functional analysis of a
Pleurotus ostreatus member. Microbiology 151:457–466.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Farah MA, Bose S, Lee J-H, Jung H-C, Kim Y. 2005. Analysis of glycated
insulin by MALDI-TOF mass spectrometry. Biochim Biophys Acta
1725:269–282.
Fauré R, Saura-Valls M, Brumer H, III, Planas A, Cottaz S, Driguez H. 2006.
Synthesis of a library of xylogluco-oligosaccharides for active-site
mapping of xyloglucan endo-transglycosylase. J Org Chem 71:5151–
5161.
Fekete A, Hoogerhout P, Zomer G, Kubler-Kielb J, Schneerson R, Robbins
JB, Pozsgay V. 2006. Synthesis of octa- and dodecamers of D-ribitol-1phosphate and their protein conjugates. Carbohydr Res 341:2037–
2048.
Fenaille F, Parisod V, Visani P, Populaire S, Tabet J-C, Guy PA. 2006.
Modifications of milk constituents during processing: A preliminary
benchmarking study. Int Dairy J 16:728–739.
Fernandez-Megia E, Correa J, Rodriguez-Meizoso I, Riguera R. 2006. A click
approach to unprotected glycodendrimers. Macromolecules 39:2113–
2120.
Ferrara C, Brunker P, Suter T, Moser S, Puntener U, Umana P. 2006a.
Modulation of therapeutic antibody effector functions by glycosylation
engineering: Influence of Golgi enzyme localization domain and coexpression of heterologous b-1, 4-N-acetylglucosaminyltransferase III
and Golgi alpha-mannosidase II. Biotechnol Bioeng 93:851–861.
Ferrara C, Stuart F, Sondermann P, Brünker P, Umaña P. 2006b. The
carbohydrate at FcgRIIIa Asn-162. An element required for high
affinity binding to non-fucosylated IgG glycoforms. J Biol Chem
281:5032–5036.
Figueroa-Perez I, Stadelmaier A, Deininger S, von Aulock S, Hartung T,
Schmidt RR. 2006. Synthesis of Staphylococcus aureus lipoteichoic
acid derivatives for determining the minimal structural requirements for
cytokine induction. Carbohydr Res 341:2901–2911.
Figueroa-Perez I, Stadelmaier A, Morath S, Hartung T, Schmidt RR. 2005.
Synthesis of structural variants of Staphylococcus aureus lipoteichoic
acid (LTA). Tetrahedron Asym 16:493–506.
Flieger M, Kantorová M, Halada P, Kuzma M, Pazoutová S, Stodulková E,
Kolı́nská R. 2005. Oligosaccharides produced by submerged cultures of
Claviceps africana and Claviceps sorghi. Folia Microbiol 50:198–
204.
Fraser-Reid B, Lu J, Jayaprakash KN, López JC. 2006. Synthesis of a 28-mer
oligosaccharide core of Mycobacterial lipoarabinomannan (LAM)
requires only two n-pentenyl orthoester progenitors. Tetrahedron Asym
17:2449–2463.
Fraysse N, Lindner B, Kacynski Z, Sharpova L, Holst O, Niehaus K, Poinot V.
2005. Sinorhizobium meliloti strain 1021 produces a low-molecularmass capsular polysaccharide that is a homopolymer of 3-deoxy-Dmanno-oct-2-ulosonic acid harboring a phospholipid anchor. Glycobiology 15:101–108.
Freeze HH, Aebi M. 2005. Altered glycan structures: The molecular basis of
congenital disorders of glycosylation. Curr Opin Struct Biol 15:490–
498.
Freire T, D’Alayer J, Bay S. 2006. Efficient monitoring of enzymatic
conjugation reaction by surface-enhanced laser desorption/
ionization time of flight mass spectrometry for process optimization.
Bioconjug Chem 17:559–564.
Fresno S, Jiménez N, Izquierdo L, Merino S, Corsaro MM, De Castro C,
Parrilli M, Naldi T, Regué M, Tomás JM. 2006. The ionic interaction of
Klebsiella pneumoniae K2 capsule and core lipopolysaccharide.
Microbiology 152:1807–1818.
Frolov A, Hoffmann P, Hoffmann R. 2006. Fragmentation behavior of
glycated peptides derived from D-glucose, D-fructose and D-ribose in
tandem mass spectrometry. J Mass Spectrom 41:1459–1469.
Frolov A, Singer D, Hoffmann R. 2006. Site-specific synthesis of Amadorimodified peptides on solid phase. J Peptide Sci 12:389–395.
Fujita K, Oura F, Nagamine N, Katayama T, Hiratake J, Sakata K, Kumagai H,
Yamamoto K. 2005a. Identification and molecular cloning of a novel
Mass Spectrometry Reviews DOI 10.1002/mas
&
glycoside hydrolase family of core 1 type O-glycan-specific endo-a-Nacetylgalactosaminidase from Bifidobacterium longum. J Biol Chem
280:37415–37422.
Fujita K, Yamamoto K. 2006. A remodeling system for the oligosaccharide
chains on glycoproteins with microbial endo-b-N-acetylglucosaminidases. Biochim Biophys Acta 1760:1631–1635.
Fujita Y, Naka T, Doi T, Yano I. 2005b. Direct molecular mass determination
of trehalose monomycolate from 11 species of mycobacteria by
MALDI-TOF mass spectrometry. Microbiology 151:1443–1452.
Fujita Y, Naka T, McNeil MR, Yano I. 2005c. Intact molecular characterization of cord factor (trehalose 6,6’-dimycolate) from nine species of
mycobacteria by MALDI-TOF mass spectrometry. Microbiology
151:3403–3416.
Fujiwaki T, Tasaka M, Takahashi N, Kobayashi H, Murakami Y, Shimada T,
Yamaguchi S. 2006. Quantitative evaluation of sphingolipids using
delayed extraction matrix-assisted laser desorption ionization time-offlight mass spectrometry with sphingosylphosphorylcholine as an
internal standard. J Chromatogr B 832:97–102.
Fujiyama K, Misaki R, Katsura A, Tanaka T, Furukawa A, Omasa T, Seki T.
2006. N-linked glycan structures of a mouse monoclonal antibody
produced from tobacco BY2 suspension-cultured cells. J Biosci Bioeng
101:212–218.
Fukui K, Kameyama A, Mukai Y, Takahashi K, Ikeda N, Akiyama Y,
Narimatsu H. 2006. A computational study of structure-reactivity
relationships in Na-adduct oligosaccharides in collision-induced
dissociation reactions. Carbohydr Res 341:624–633.
Fukuyama Y, Kolender AA, Nishioka M, Nonami H, Matulewicz MC, ErraBalsells R, Cerezo AS. 2005. Matrix-assisted ultraviolet laser
desorption/ionization time-of-flight mass spectrometry of b-(1-3), b(1-4)-xylans from Nothogenia fastigiata using nor-harmane as matrix.
Rapid Commun Mass Spectrom 19:349–358.
Fumoto M, Hinou H, Matsushita T, Kurogochi M, Ohta T, Ito T, Yamada K,
Takimoto A, Kondo H, Inazu T, Nishimura S-I. 2005a. Molecular
transporter between polymer platforms: Highly efficient chemoenzymatic glycopeptide synthesis by the combined use of solid-phase and
water-soluble polymer supports. Angew Chem Int Ed Engl 44:2534–
2537.
Fumoto M, Hinou H, Ohta T, Ito T, Yamada K, Takimoto A, Kondo H,
Shimizu H, Inazu T, Nakahara Y, Nishimura S-I. 2005b. Combinatorial
synthesis of MUC1 glycopeptides: Polymer blotting facilitates
chemical and enzymatic synthesis of highly complicated mucin
glycopeptides. J Am Chem Soc 127:11804–11818.
Furneaux RH, Landersjo CL, McCullough JL, Severn WB. 2005. A novel
phosphatidylinositol manno-oligosaccharide (dPIM-8) from Gordonia
sputi. Carbohydr Res 340:1618–1624.
Furuike T, Sadamoto R, Niikura K, Monde K, Sakairi N, Nishimura S-I. 2005.
Chemical and enzymatic synthesis of glycocluster having seven sialyl
lewis X arrays using b-cyclodextrin as a key scaffold material.
Tetrahedron 61:1737–1742.
Fuse T, Ando H, Imamura A, Sawada N, Ishida H, Kiso M, Ando T, Li S-C, Li
Y-T. 2006. Synthesis and enzymatic susceptibility of a series of novel
GM2 analogs. Glycoconj J 23:329–343.
Gama CI, Hsieh-Wilson LC. 2005. Chemical approaches to deciphering the
glycosaminoglycan code. Curr Opin Chem Biol 9:609–619.
Gandolfi-Donadı́o L, Gola G, de Lederkremer RM, Gallo-Rodriguez C. 2006.
Synthesis of a-D-Galf-(1-2)-D-galactitol and a-D-Galf-(1-2)[b-D-Galf(1-3)]-D-galactitol, oligosaccharide derivatives from Bacteroides cellulosolvens glycoproteins. Carbohydr Res 341:2487–2497.
Gao C, Miyoshi E, Uozumi N, Takamiya R, Wang X, Noda K, Gu J, Honke K,
Wada Y, Taniguchi N. 2005a. Bisecting GlcNAc mediates the binding of
annexin V to Hsp47. Glycobiology 15:1067–1075.
Gao Y, Eguchi A, Kakehi K, Lee YC. 2005b. Synthesis and molecular
recognition of carbohydrate-centered multivalent glycoclusters by a
plant lectin RCA120. Bioorg Med Chem 13:6151–6157.
79
&
HARVEY
Geiser H, Silvescu C, Reinhold V. 2006. Structural approaches to
glycoproteomics. In: Smejkal GB, Lazarev A, editors. Separation
methods in proteomics. Boca Raton, FL: CRC Press. pp 321-343.
Gemma E, Lahmann M, Oscarson S. 2006. Synthesis of monodeoxy
analogues of the trisaccharide a-D-Glcp-(1-3)-a-D-Manp-(1-2)-a-DManpOMe recognised by Calreticulin/Calnexin. Carbohydr Res
341:1533–1542.
Gerlach D, Schlott B, Zähringer U, Schmidt K-H. 2005. N-acetyl-Dgalactosamine/N-acetyl-D-glucosamine-recognizing lectin from the
snail Cepaea hortensis: Purification, chemical characterization, cloning
and expression in E. coli. FEMS Immunol Med Microbiol 43:223–
232.
Geyer H, Geyer R. 2006. Strategies for analysis of glycoprotein glycosylation. Biochim Biophys Acta 1764:1853–1869.
Geyer H, Wuhrer M, Resemann A, Geyer R. 2005. Identification and
characterization of keyhole limpet hemocyanin N-glycans mediating
cross-reactivity with Schistosoma mansoni. J Biol Chem 280:40731–
40748.
Ghera BB, Fache F, Parrot-Lopez H. 2006. Use of the olefin metathesis
reaction for highly efficient b-cyclodextrin modification. Tetrahedron
62:4807–4813.
Ghesquière B, Van Damme J, Martens L, Vandekerckhove J, Gevaert K. 2006.
Proteome-wide characterization of N-glycosylation events by diagonal
chromatography. J Proteome Res 5:2438–2447.
Ghosh P, Ghosal P, Thakur S, Lerouge P, Loutelier-Bourhis CL, Driouich A,
Ray B. 2005. Polysaccharides from Sesamum indicum meal: Isolation
and structural features. Food Chem 90:719–726.
Gibbons HS, Kalb SR, Cotter RJ, Raetz CRH. 2005. Role of Mg2þ and pH in
the modification of Salmonella lipid A after endocytosis by macrophage
tumour cells. Mol Microbiol 55:425–440.
Gibeaut DM, Pauly M, Bacic A, Fincher GB. 2005. Changes in cell wall
polysaccharides in developing barley (Hordeum vulgare) coleoptiles.
Planta 221:729–738.
Gibson KJC, Gilleron M, Constant P, Sichi B, Puzo G, Besra GS, Nigou J.
2005. A lipomannan variant with strong TLR-2-dependent proinflammatory activity in Saccharothrix aerocolonigenes. J Biol Chem
280:28347–28356.
Gilleron M, Garton NJ, Nigou J, Brando T, Puzo G, Sutcliffe IC. 2005.
Characterization of a truncated lipoarabinomannan from the actinomycete Turicella otitidis. J Bacteriol 187:854–861.
Gilleron M, Lindner B, Puzo G. 2006. MS/MS Approach for characterization
of the fatty acid distribution on mycobacterial phosphatidyl-myoinositol mannosides. Anal Chem 78:8543–8548.
Gilleron M, Nigou J, Nicolle D, Quesniaux V, Puzo G. 2006. The acylation
state of mycobacterial lipomannans modulates innate immunity
response through toll-like receptor 2. Chem Biol 13:39–47.
Glebko LI, Krasovskaj NP, Strigina LI, Ulanova KP, Denisenko VA,
Dmitrenok PS. 2002. Triterpene glycosides from Pulsatilla chinensis.
Russ Chem Bull 51:1945–1950.
Glover KJ, Weerapana E, Chen MM, Imperiali B. 2006. Direct biochemical
evidence for the utilization of UDP-bacillosamine by PglC, an essential
glycosyl-1-phosphate transferase in the Campylobacter jejuni N-linked
glycosylation pathway. Biochemistry 45:5343–5350.
Glover KJ, Weerapana E, Imperiali B. 2005. In vitro assembly of the
undecaprenylpyrophosphate linked heptasaccharide for prokaryotic
N-linked glycosylation. Proc Natl Acad Sci USA 102:14255–
14259.
Glover KJ, Weerapana E, Numao S, Imperiali B. 2005. Chemoenzymatic
synthesis of glycopeptides with PglB, a bacterial oligosaccharyl
transferase from Campylobacter jejuni. Chem Biol 12:1311–1315.
Godevac D, Mandic B, Vajs V, Teševic V, Menkovic N, Janackovic P,
Milosavljevic S. 2006. Triterpenoid saponins and iridoid glycosides
from the aerial parts of Cephalaria pastricensis. Biochem Syst Ecol
34:890–893.
80
Goldberg D, Bern M, Li B, Lebrilla CB. 2006. Automatic determination of Oglycan structure from fragmentation spectra. J Proteome Res 5:1429–
1434.
Goldberg D, Sutton-Smith M, Paulson J, Dell A. 2005. Automatic annotation
of matrix-assisted laser desorption/ionization N-glycan spectra. Proteomics 5:865–875.
Gomes RA, Miranda HV, Silva MS, Graca G, Coelho AV, Ferreira AE,
Cordeiro C, Freire AP. 2006. Yeast protein glycation in vivo by
methylglyoxal: Molecular modification of glycolytic enzymes and heat
shock proteins. FEBS J 273:5273–5287.
Gomez SR, Xing DK-L, Corbel MJ, Coote J, Parton R, Yuen C-T. 2006.
Development of a carbohydrate binding assay for the B-oligomer of
pertussis toxin and toxoid. Anal Biochem 356:244–253.
Gómez-Garcı́a M, Benito JM, Rodrı́guez-Lucena DR, Yu J-X, Chmurski K,
Mellet CO, Gallego RG, Maestre A, Defaye J, Fernández JMG. 2005.
Probing secondary carbohydrate-protein interactions with highly dense
cyclodextrin-centered heteroglycoclusters: The heterocluster effect. J
Am Chem Soc 127:7970–7971.
Gormann R, Kaloga M, Ferreira D, Marais JPJ, Kolodziej H. 2006.
Newbouldiosides A-C, phenylethanoid glycosides from the stem bark
of Newbouldia laevis. Phytochemistry 67:805–811.
Goto K, Miura T, Mizuno M. 2005. Synthesis of peptides and oligosaccharides by using a recyclable fluorous tag. Tetrahedron Lett 46:8293–8297.
Goubet F, Ström A, Quéméner B, Stephens E, Williams MAK, Dupree P.
2006. Resolution of the structural isomers of partially methylesterified
oligogalacturonides by polysaccharide analysis using carbohydrate gel
electrophoresis. Glycobiology 16:29–35.
Gray JSS, Montgomery R. 2006. Asymmetric glycosylation of soybean seed
coat peroxidase. Carbohydr Res 341:198–209.
Graziani A, Amer H, Zamyatina A, Hofinger A, Kosma P. 2005. Synthesis of
C-glycosides related to glycero-b-D-manno-heptoses. Tetrahedron
Asym 16:167–175.
Greimel P, Jabs S, Storch S, Cherif S, Honke K, Braulke T, Thiem J. 2006. In
vitro sulfation of N-acetyllactosaminide by soluble recombinant human
b-Gal-30 -sulfotransferase. Carbohydr Res 341:918–924.
Griebl A, Lange T, Weber H, Milacher W, Sixta H. 2006. Xylooligosaccharide (XOS) formation through hydrothermolysis of xylan
derived from viscose process. Macromol Symp 232:107–120.
Grombe R, Gouzy M-F, Nitschke M, Komber H, Werner C. 2006. Preparation
and characterization of glycosylated maleic anhydride copolymer thin
films. Colloids Surf A 284–285:295–300.
Grün CH, van Vliet SJ, Schiphorst WECM, Bank CMC, Meyer S, van Die I,
van Kooyk Y. 2006. One-step biotinylation procedure for carbohydrates
to study carbohydrate-protein interactions. Anal Biochem 254:54–63.
Gu G, Liu H, Pinto BM. 2006. Facile synthesis of sulfonium ion derivatives of
1,5-anhydro-5-thio-L-fucitol as potential a-L-fucosidase inhibitors.
Carbohydr Res 341:2478–2486.
Gu L, Lin Y, Qu L, Sun Y-P. 2006. Carbon nanotubes as a scaffold to display
paired sugars in solution. Biomacromolecules 7:400–402.
Guérardel Y, Chang L-Y, Maes E, Huang C-J, Khoo K-H. 2006. Glycomic
survey mapping of zebrafish identifies unique sialylation pattern.
Glycobiology 16:244–257.
Guérardel Y, Leleu D, Coppin A, Liénard L, Slomianny C, Strecker G, Ball S,
Tomavo S. 2005. Amylopectin biogenesis and characterization in
the protozoan parasite Toxoplasma gondii, the intracellular development of which is restricted in the HepG2 cell line. Microbes Infect
7:41–48.
Guerrini M, Guglieri S, Santarsiero R, Vismara E. 2005. Synthesis and
characterisation of hexa- and tetrasaccharide mimics from acetobromomaltotriose and acetobromomaltose, and of C-disaccharide mimics
from acetobromoglucose, obtained by electrochemical reduction on
silver. Tetrahedron Asym 16:243–253.
Guillaumie F, Justesen SFL, Mutenda KE, Roepstorff P, Jensen KJ, Thomas
ORT. 2006. Fractionation, solid-phase immobilization and chemical
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
degradation of long pectin oligogalacturonides. Initial steps towards
sequencing of oligosaccharides. Carbohydr Res 341:118–129.
Gupta S, Sage A, Singh AK. 2005. Screening and confirmation of
recombinant human erythropoietin and darbepoietin-a in spiked
plasma samples from drug-free horses. Anal Chim Acta 552:96–
109.
Gur’yanov O, Gorshkova T, Kabel M, Schols H, Van Dam JEG. 2006.
Structural characterization of tissue-specific galactan from flax fibers by
1
H NMR and MALDI TOF mass spectrometry. Russ J Bioorg Chem
32:558–567.
Gustavsson MT, Persson PV, Iversen T, Martinelle M, Hult K, Teeri TT,
Brumer H III. 2005. Modification of cellulose fiber surfaces by use of a
lipase and a xyloglucan endotransglycosylase. Biomacromolecules
6:196–203.
Hackenberger CPR, O’Reilly MK, Imperiali B. 2005. Improving glycopeptide synthesis: A convenient protocol for the preparation of bglycosylamines and the synthesis of glycopeptides. J Org Chem 70:
3574–3578.
Hada N, Jin Y, Takeda T, Ohtsuka I, Yokoyama S. 2006a. Syntheses of new
model compounds related to an antigenic epitope from Bupleurum
falcatum L. and their distributions in various ganglioside-phospholipid
monolayers. Chem Pharm Bull 54:1281–1284.
Hada N, Oka J, Nishiyama A, Takeda T. 2006b. Stereoselective synthesis of
1,2-cis-galactosides: Synthesis of a glycolipid containing Gala1-6Gal
component from Zygomycetes species. Tetrahedron Lett 47:6647–
6650.
Hada N, Sato K, Jin Y, Takeda T. 2005. Synthesis of new peptidic
glycoclusters derived from b-alanine. Part 2: Optionally modulated
distance between side-chain branched points. Chem Pharm Bull 53:
1131–1135.
Hada N, Sonoda Y, Takeda T. 2006. Synthesis of a novel glycosphingolipid
from the millipede, Parafontaria laminata armigera, and the assembly
of its carbohydrate moiety into multivalent structures. Carbohydr Res
341:1341–1352.
Hagihara S, Totani K, Ito Y. 2006. Exploration of oligosaccharide-protein
interactions in glycoprotein quality control by synthetic approaches.
Chem Record 6:290–302.
Haginoya E, Hojo H, Nakahara Y, Nakahara Y, Nabeshima K, Toole BP,
Watanabe Y. 2006. Synthesis of a glycosylated peptide thioester by the
Boc strategy and its application to segment condensation. Biosci
Biotechnol Biochem 70:1338–1349.
Hainrichson M, Pokrovskaya V, Shallom-Shezifi D, Fridman M, Belakhov V,
Shachar D, Yaron S, Baasov T. 2005. Branched aminoglycosides:
Biochemical studies and antibacterial activity of neomycin B
derivatives. Bioorg Med Chem 13:5797–5807.
Hajjar AM, Harvey MD, Shaffer SA, Goodlett DR, Sjöstedt A, Edebro H,
Forsman M, Byström M, Pelletier M, Wilson CB, Miller SI, Skerrett SJ,
Ernst RK. 2006. Lack of in vitro and in vivo recognition of Francisella
tularensis subspecies lipopolysaccharide by toll-like receptors. Infect
Immun 74:6730–6738.
Halkes KM, Carvalho de Souza A, Maljaars CEP, Gerwig GJ, Kamerling JP.
2005. A facile method for the preparation of gold glyconanoparticles
from free oligosaccharides and their applicability in carbohydrateprotein interaction studies. Eur J Org Chem:3650–3659.
Hamcerencu M, Popa M, Riess G, Ritter H, Alupei V. 2005. Unsaturated
esters of cyclodextrin—Synthesis and characterization. Cellulose
Chem Technol 39:389–413.
Hamed AI, Plaza A, Balestrieri ML, Mahalel UA, Springuel IV, Oleszek W,
Pizza C, Piacente S. 2006. Cardenolide glycosides from Pergularia
tomentosa and their proapoptotic activity in Kaposi’s sarcoma cells. J
Nat Prod 69:1319–1322.
Hanashima S, Inamori K-I, Manabe S, Taniguchi N, Ito Y. 2006. Systematic
synthesis of bisubstrate-type inhibitors of N-acetylglucosaminyltransferases. Chem Eur J 12:3449–3462.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Haneda K, Takeuchi M, Tagashira M, Inazu T, Toma K, Isogai Y, Hori M,
Kobayashi K, Takeuchi M, Takegawa M, Yamamoto M. 2006. Chemoenzymatic synthesis of eel calcitonin glycosylated at two sites with the
same and different carbohydrate structures. Carbohydr Res 341:181–
190.
Hanneman AJ, Rosa JC, Ashline D, Reinhold VN. 2006. Isomer and glycomer
complexities of core GlcNAcs in Caenorhabditis elegans. Glycobiology 16:874–890.
Haque A, Kotake T, Tsumuraya Y. 2005. Mode of action of b-glucuronidase
from Aspergillus niger on the sugar chains of arabinogalactan-protein.
Biosci Biotechnol Biochem 69:2170–2177.
Harcum SW. 2005. Protein glycosylation. In: Ozturk SS, Hu W-S, editors.
Cell culture technology for pharmaceutical and cell-based therapies.
Boca Raton, FL: CRC Press. pp 113-154.
Harrison RL, Jarvis DL. 2006. Protein N-glycosylation in the baculovirusinsect cell expression system and engineering of insect cells to produce
‘‘mammalianized’’ recombinant glycoproteins. Adv Virus Res 68:159–
191.
Hartley G, Taylor R, Prior J, Newstead S, Hitchen PG, Morris HR, Dell A,
Titball RW. 2006. Grey variants of the live vaccine strain of Francisella
tularensis lack lipopolysaccharide O-antigen, show reduced ability to
survive in macrophages and do not induce protective immunity in mice.
Vaccine 24:989–996.
Hartman J, Albertsson A-C, Sjöberg J. 2006. Surface- and bulk-modified
galactoglucomannan hemicellulose films and film laminates for
versatile oxygen barriers. Biomacromolecules 7:1983–1989.
Harvey DJ. 1999. Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. Mass Spectrom Rev 18:349–451.
Harvey DJ. 2005a. Fragmentation of negative ions from carbohydrates: Part
2, Fragmentation of high-mannose N-linked glycans. J Am Soc Mass
Spectrom 16:631–646.
Harvey DJ. 2005b. Fragmentation of negative ions from carbohydrates: Part
1; Use of nitrate and other anionic adducts for the production of negative
ion electrospray spectra from N-linked carbohydrates. J Am Soc Mass
Spectrom 16:622–630.
Harvey DJ. 2005c. Fragmentation of negative ions from carbohydrates: Part
3, Fragmentation of hybrid and complex N-linked glycans. J Am Soc
Mass Spectrom 16:647–659.
Harvey DJ. 2005d. Proteomic analysis of glycosylation: Structural determination of N- and O-linked glycans by mass spectrometry. Expert Rev
Proteomics 2:87–101.
Harvey DJ. 2005e. Structural determination of N-linked glycans by matrixassisted laser desorption/ionization and electrospray ionization mass
spectrometry. Proteomics 5:1774–1786.
Harvey DJ. 2006. Analysis of carbohydrates and glycoconjugates by matrixassisted laser desorption/ionization mass spectrometry: An update
covering the period 1999–2000. Mass Spectrom Rev 25:595–662.
Harvey DJ. 2008a. Analysis of carbohydrates and glycoconjugates by matrixassisted laser desorption/ionization mass spectrometry: An update
covering the period 2001–2002. Mass Spectrom Rev 27:125–201.
Harvey DJ. 2009. Analysis of carbohydrates and glycoconjugates by matrixassisted laser desorption/ionization mass spectrometry: An update
covering the period 2003–2004. Mass Spectrom Rev 28:273–361.
Harvey DJ, Bousfield GR. 2005. Differentiation between sulphated and
phosphated carbohydrates in low-resolution matrix-assisted laser
desorption/ionization mass spectra. Rapid Commun Mass Spectrom
19:287–288.
Harvey DJ, Dwek RA, Rudd PM. 2006. Determining the structure of glycan
moieties by mass spectrometry. In: Coligan JE, Dunn BM, Speicher
DW, Wingfield PT, editors. Current protocols in protein science. New
York: J. Wiley and Sons Inc. p UNIT 12.17.
Hasegawa T, Umeda M, Numata M, Li C, Bae A-H, Fujisawa T, Haraguchi S,
Sakurai K, Shinkai S. 2006. ‘Click chemistry’ on polysaccharides: A
convenient, general, and monitorable approach to develop (1-3)-b-D-
81
&
HARVEY
glucans with various functional appendages. Carbohydr Res 341:
35–40.
Hasegawa Y, Miyauchi M, Takashima Y, Yamaguchi H, Harada A. 2005.
Supramolecular polymers formed from b-cyclodextrins dimer linked by
poly(ethylene glycol) and guest dimers. Macromolecules 38:3724–
3730.
Hashimoto K, Goto S, Kawano S, Aoki-Kinoshita KF, Ueda N, Hamajima M,
Kawasaki T, Kanehisa M. 2006. KEGG as a glycome informatics
resource. Glycobiology 16:63R–70R.
Haslam SM, Khoo KH, Dell A. 2006. Sequencing of oligosaccharides and
glycoproteins. In: Wong C-H, editor. Carbohydrate-based drug
discovery. Hoboken, NJ: Wiley VCH. pp 461–482.
Haslam SM, North SJ, Dell A. 2006. Mass spectrometric analysis of N- and Oglycosylation of tissues and cells. Curr Opin Struct Biol 16:584–591.
Hattori K, Kenmoku A, Mizuguchi T, Ikeda D, Mizuno M, Inazu T. 2006.
Saccharide-branched cyclodextrins as targeting drug carriers. J Incl
Phenom Macrocyclic Chem 56:9–15.
Hayase F, Usui T, Watanabe H. 2006. Chemistry and some biological effects
of model melanoidins and pigments as Maillard intermediates. Mol
Nutr Food Res 50:1171–1179.
Hayashida O, Takaoka Y, Hamachi I. 2005. Synthesis and guest-binding study
of polytopic multi(cyclophane) hosts. Tetrahedron Lett 46:6589–6592.
Hederos M, Konradsson P. 2005a. Synthesis of the core tetrasaccharide of
Trypanosoma cruzi glycoinositolphospholipids: Manp(1-6)-Manp(14)-6-(2-aminoethylphosphonic acid)-GlcNp(1-6)-myo-Ins-1-PO4. J
Org Chem 70:7196–7207.
Hederos M, Konradsson P. 2005b. Efficient routes to ethyl-2-deoxy-2phthalimido-1-b-D-thio-galactosamine derivatives via epimerization of
the corresponding glucosamine compounds. J Carbohydr Chem
24:297–320.
Heiner S, Detert H, Kuhn A, Kunz H. 2006. Hydrophilic photolabelling of
glycopeptides from the murine liver-intestine (LI) cadherin recognition
domain. Bioorg Med Chem 14:6149–6164.
Higai K, Aoki Y, Azuma Y, Matsumoto K. 2005. Glycosylation of sitespecific glycans of a1-acid glycoprotein and alterations in acute and
chronic inflammation. Biochim Biophys Acta 1725:128–135.
Higson AP, Ross AJ, Tsvetkov YE, Routier FH, Sizova OV, Ferguson MAJ,
Nikolaev AV. 2005. Synthetic fragments of antigenic lipophosphoglycans from Leishmania major and Leishmania mexicana and their use for
characterisation of the Leishmania elongating a-D-mannopyranosylphosphate transferase. Chem Eur J 11:2019–2030.
Hilz H, de Jong LE, Kabel MA, Schols HA, Voragen AGJ. 2006. A
comparison of liquid chromatography, capillary electrophoresis, and
mass spectrometry methods to determine xyloglucan structures in black
currants. J Chromatogr A 1133:275–286.
Hinckley MB, Reynolds CM, Ribeiro AA, McGrath SC, Cotter RJ, Lauw FN,
Golenbock DT, Raetz CRH. 2005. A Leptospira interrogans enzyme
with similarity to yeast Ste14p that methylates the 1-phosphate group of
lipid A. J Biol Chem 280:30214–30224.
Hinz SWA, Pastink MI, van den Broek LAM, Vincken J-P, Voragen AGJ.
2005a. Bifidobacterium longum endogalactanase liberates galactotriose
from type I galactans. Appl Environ Microbiol 71:5501–5510.
Hinz SWA, Verhoef R, Schols HA, Vincken J-P, Voragen AGJ. 2005b. Type I
arabinogalactan contains b-D-Galp-(1-3)-b-D-Galp structural elements.
Carbohydr Res 340:2135–2143.
Hirano K, Sakai S, Ishikawa T, Avci FY, Linhardt RJ, Toida T. 2005.
Preparation of the methyl ester of hyaluronan and its enzymatic
degradation. Carbohydr Res 340:2297–2304.
Hitchen PG, Dell A. 2005. Bacterial glycoproteomics. Microbiology
152:1575–1580.
Hocquelet C, Blu J, Jankowski CK, Arseneau S, Buisson D, Mauclaire L.
2006. Synthesis of calixarene-cyclodextrin coupling products. Tetrahedron 62:11963–11971.
82
Hodoniczky J, Zheng YZ, James DC. 2005. Control of recombinant
monoclonal antibody effector functions by Fc N-glycan remodeling
in vitro. Biotechnol Prog 21:1644–1652.
Hoffman M, Jia Z, Peña MJ, Cash M, Harper A, Blackburn ARI, Darvill A,
York WS. 2005. Structural analysis of xyloglucans in the primary cell
walls of plants in the subclass Asteridae. Carbohydr Res 340:1826–
1840.
Höije A, Sandström C, Roubroeks JP, Andersson R, Gohil S, Gatenholm P.
2006. Evidence of the presence of 2-O-b-D-xylopyranosyl-a-Larabinofuranose side chains in barley husk arabinoxylan. Carbohydr
Res 341:2959–2966.
Hojo H, Matsumoto Y, Nakahara Y, Ito E, Suzuki Y, Suzuki M, Suzuki A,
Nakahara Y. 2005. Chemical synthesis of 23 kDa glycoprotein by
repetitive segment condensation: A synthesis of MUC2 basal motif
carrying multiple O-GalNAc moieties. J Am Chem Soc 127:13720–
13725.
Hölemann A, Stocker BL, Seeberger PH. 2006. Synthesis of a core
arabinomannan oligosaccharide of Mycobacterium tuberculosis. J
Org Chem 71:8071–8088.
Holmes BJ, Petrucci GA. 2006. Water-soluble oligomer formation from acidcatalyzed reactions of levoglucosan in proxies of atmospheric aqueous
aerosols. Environ Sci Technol 40:4983–4989.
Holtan S, Bruheim P, Skjak-Braek G. 2006. Mode of action and subsite
studies of the guluronan block-forming mannuronan C-5 epimerases
AlgE1 and AlgE6. Biochem J 395:319–329.
Hossler P, Goh L-T, Lee MM, Hu W-S. 2006. GlycoVis: Visualizing glycan
distribution in the protein N-glycosylation pathway in mammalian cells.
Biotechnol Bioeng 95:946–960.
Hotha S, Kashyap S. 2006a. ‘‘Click chemistry’’ inspired synthesis of pseudooligosaccharides and amino acid glycoconjugates. J Org Chem 71:364–
367.
Hotha S, Kashyap S. 2006b. ‘‘Click chemistry’’ inspired synthesis of pseudooligosaccharides and amino acid glycoconjugates. J Org Chem 71:852.
Hsu J, Chang SJ, Franz AH. 2006. MALDI-TOF and ESI-MS analysis of
oligosaccharides labeled with a new multifunctional oligosaccharide
tag. J Am Soc Mass Spectrom 17:194–204.
Huang K-T, Wu B-C, Lin C-C, Luo S-C, Chen C, Wong C-H, Lin C-C. 2006.
Multi-enzyme one-pot strategy for the synthesis of sialyl Lewis Xcontaining PSGL-1 glycopeptide. Carbohydr Res 341:2151–2155.
Huang R, Mendis E, Kim S-K. 2005. Improvement of ACE inhibitory activity
of chitooligosaccharides (COS) by carboxyl modification. Bioorg Med
Chem 13:3649–3655.
Huang Y, Konse T, Mechref Y, Novotny MV. 2002. Matrix-assisted laser
desorption/ionization mass spectrometry compatible b-elimination of
O-linked oligosaccharides. Rapid Commun Mass Spectrom 16:1199–
1204.
Huck CW, Bakry R, Huber LA, Bonn GK. 2006. Progress in capillary
electrophoresis coupled to matrix-assisted laser desorption/ionizationtime of flight mass spectrometry. Electrophoresis 27:2063–2074.
Ibey BL, Beier HT, Rounds RM, Coté GL, Yadavalli VK, Pishko MV. 2005.
Competitive binding assay for glucose based on glycodendrimerfluorophore conjugates. Anal Chem 77:7039–7046.
Ibrahem I, Córdova A. 2005. Amino acid catalyzed direct enantioselective
formation of carbohydrates: One-step de novo synthesis of ketoses.
Tetrahedron Lett 46:3363–3367.
Iglesias N, Abelenda JA, Rodino M, Sampedro J, Revilla G, Zarra I. 2006.
Apoplastic glycosidases active against xyloglucan oligosaccharides of
Arabidopsis thaliana. Plant Cell Physiol 47:55–63.
Iijima J, Zhao Y, Isaji T, Kameyama A, Nakaya S, Wang X, Ihara H, Cheng X,
Nakagawa T, Miyoshi E, Kondo A, Narimatsu H, Taniguchi N, Gu J.
2006. Cell-cell interaction-dependent regulation of N-acetylglucosaminyltransferase III and the bisected N-glycans in GE11 epithelial cells:
Involvement of E-cadherin-mediated cell adhesion. J Biol Chem
281:13038–13046.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Immerzeel P, Eppink MM, De Vries SC, Schols HA, Voragen AGJ. 2006.
Carrot arabinogalactan proteins are interlinked with pectins. Physiol
Plant 128:18–28.
Imre T, Schlosser G, Pocsfalvi G, Siciliano R, Molnár-Szöllsi É, Kremmer T,
Malorni A, Vékey K. 2005. Glycosylation site analysis of human alpha1-acid glycoprotein (AGP) by capillary liquid chromatography–
electrospray mass spectrometry. J Mass Spectrom 40:1472–1483.
Inamori K, Mita S, Gu J, Mizuno-Horikawa Y, Miyoshi E, Dennis JW,
Taniguchi N. 2006. Demonstration of the expression and the enzymatic
activity of N-acetylglucosaminyltransferase IX in the mouse brain.
Biochim Biophys Acta 1760:678–684.
Inamura S, Fujimoto Y, Kawasaki A, Shiokawa Z, Woelk E, Heine H, Lindner
B, Inohara N, Kusumoto S, Fukase K. 2006. Synthesis of peptidoglycan
fragments and evaluation of their biological activity. Org Biomol Chem
4:232–242.
Inforzato A, Peri G, Doni A, Garlanda C, Mantovani A, Bastone A,
Carpentieri A, Amoresano A, Pucci P, Roos A, Daha MR, Vincenti S,
Gallo G, Carminati P, De Santis R, Salvatori G. 2006. Structure and
function of the long pentraxin PTX3 glycosidic moiety: Fine-tuning of
the interaction with C1q and complement activation. Biochemistry
45:11540–11551.
Inoue Y, Miyauchi M, Nakajima H, Takashima Y, Yamaguchi H, Harada A.
2006. Self-threading of a poly(ethylene glycol) chain in a cyclodextrinring: Control of the exchange dynamics by chain length. J Am Chem Soc
128:8994–8995.
Ishiwata A, Akao H, Ito Y. 2006. Stereoselective synthesis of a fragment of
mycobacterial arabinan. Org Lett 8:5525–5528.
Ishiwata A, Akao H, Ito Y, Sunagawa M, Kusunose N, Kashiwazaki Y. 2006.
Synthesis and TNF-a inducing activities of mycoloyl-arabinan motif of
mycobacterial cell wall components. Bioorg Med Chem 14:3049–
3061.
Ishiwata A, Ohta S, Ito Y. 2006. A stereoselective 1,2-cis glycosylation
toward the synthesis of a novel N-linked glycan from the Gram-negative
bacterium, Campylobacter jejuni. Carbohydr Res 341:1557–1573.
Ito H, Kameyama A, Sato T, Kiyohara K, Nakahara Y, Narimatsu H.
2005. Molecular-weight-tagged glycopeptide library: Efficient
construction and applications. Angew Chem Int Ed Engl 44:4547–
4549.
Ito K, Miyagawa K, Matsumoto M, Yabuno S, Kawakami N, Hamaguchi T,
Iizuka M, Minamiura N. 2006. Evidence for the transglycosylation of
complex type oligosaccharides of glycoproteins by endo-b-N-acetylglucosaminidase HS. Arch Biochem Biophys 454:89–99.
Itoh Y, Wang X, Hinnebusch J, Preston JF III, Romeo T. 2005.
Depolymerization of b-1,6-N-acetyl-D-glucosamine disrupts the integrity of diverse bacterial biofilms. J Bacteriol 187:382–387.
Ivleva VB, Sapp LM, O’Connor PB, Costello CE. 2005. Ganglioside analysis
by thin-layer chromatography matrix-assisted laser desorption/ionization orthogonal time-of-flight mass spectrometry. J Am Soc Mass
Spectrom 16:1552–1560.
Izumi M, Tsuruta O, Kajihara Y, Yazawa S, Yuasa H, Hashimoto H. 2005.
Synthesis and evaluation of 5-thio-L-fucose-containing oligosaccharide. Chem Eur J 11:3032–3038.
Jacques S, Rich JR, Ling CC, Bundle DR. 2006. Chemoenzymatic synthesis
of GM3 and GM2 gangliosides containing a truncated ceramide
functionalized for glycoconjugate synthesis and solid phase applications. Org Biomol Chem 4:142–154.
Jacquet R, Favetta P, Elfakir C, Lafosse M. 2005. Characterization of a new
methylated b-cyclodextrin with a low degree of substitution by matrixassisted laser desorption/ionization mass spectrometry and liquid
chromatography using evaporative light scattering detection. J
Chromatogr A 1083:106–112.
Jain N, Kumar A, Chauhan S, Chauhan SMS. 2005. Chemical and
biochemical transformations in ionic liquids. Tetrahedron 61:1015–
1060.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Jang-Lee J, North SJ, Sutton-Smith M, Goldberg D, Panico M, Morris H,
Haslam S, Dell A. 2006. Glycomic profiling of cells and tissues by mass
spectrometry: Fingerprinting and sequencing methodologies. Methods
Enzymol 415:59–86.
Jankowska M, Mada J. 2005. Glycosylation of allyl 2-acetamido-4,6-Obenzylidene-2-deoxy-a-D-glucopyranoside with bulky substituted glycosyl donors. Carbohydr Res 340:2048–2051.
Janssen S, Schmidt RR. 2005. Synthesis of ganglioside mimics for binding
studies with myelin-associated glycoprotein (MAG). J Carbohydr
Chem 24:611–647.
Jayachandran R, Radcliffe CM, Royle L, Harvey DJ, Dwek RA, Rudd PM,
Karande AA. 2006. Oligosaccharides modulate the apoptotic activity of
glycodelin. Glycobiology 16:1052–1063.
Jia Z, Cash M, Darvill AG, York WS. 2005. NMR characterization of
endogenously O-acetylated oligosaccharides isolated from tomato
(Lycopersicon esculentum) xyloglucan. Carbohydr Res 340:1818–
1825.
Jin Y, Hada N, Oka J, Kanie O, Daikoku S, Kanie Y, Yamada H, Takeda T.
2006. Syntheses of model compounds related to an antigenic epitope in
pectic polysaccharides from Bupleurum falcatum L. (II). Chem Pharm
Bull 54:485–492.
Joddar B, Ramamurthi A. 2006. Elastogenic effects of exogenous hyaluronan
oligosaccharides on vascular smooth muscle cells. Biomaterials
27:5698–5707.
Johansson SMC, Arnberg N, Elofsson M, Wadell G, Kihlberg J. 2005.
Multivalent HSA conjugates of 3-sialyllactose are potent inhibitors
of adenoviral cell attachment and infection. ChemBioChem 6:358–
364.
Johnston BD, Jensen HH, Pinto BM. 2006. Synthesis of sulfonium sulfate
analogues of disaccharides and their conversion to chain-extended
homologues of salacinol: New glycosidase inhibitors. J Org Chem
71:1111–1118.
Jonke S, Liu K-G, Schmidt RR. 2006. Solid-phase oligosaccharide synthesis
of a small library of N-glycans. Chem Eur J 12:1274–1290.
Joosten JAF, Tholen NTH, El Maate FA, Brouwer AJ, van Esse GW, Rijkers
DTS, Liskamp RMJ, Pieters RJ. 2006. High-yielding microwaveassisted synthesis of triazole-linked glycodendrimers by coppercatalyzed [3 þ 2] cycloaddition. Eur J Org Chem:3182–3185.
Jørgensen CT, Svendsen A, Brask J. 2005. Enzymatic synthesis of
oligosaccharides from branched cyclodextrins. Carbohydr Res
340:1233–1237.
Jung H, Kim YH, Kim S. 2005. Structural basis for the presence of a
monoglucosylated oligosaccharide in mature glycoproteins. Biochem
Biophys Res Commun 331:100–106.
Jung Y, Park H, Cho E, Jung S. 2005. Structural analyses of novel
glycerophosphorylated a-cyclosophorohexadecaoses isolated from X.
campestris pv. campestris. Carbohydr Res 340:673–677.
Jürs S, Thiem J. 2005. Alternative approaches towards glycosylated eightmembered ring compounds employing Claisen rearrangement of mono
and disaccharide allyl vinyl ether precursors. Tetrahedron Asym
16:1631–1638.
Kahler CM, Lyons-Schindler S, Choudhury B, Glushka J, Carlson RW,
Stephens DS. 2006. O-acetylation of the terminal N-acetylglucosamine
of the lipooligosaccharide inner core in Neisseria meningitidis.
Influence on inner core structure and assembly. J Biol Chem
281:19939–19948.
Kajimura J, Rahman A, Hsu J, Evans MR, Gardner KH, Rick PD. 2006. Oacetylation of the enterobacterial common antigen polysaccharide is
catalyzed by the product of the yiaH gene of Escherichia coli K-12. J
Bacteriol 188:7542–7550.
Kaltashov IA, Eyles SJ. 2005. Mass spectrometry in biophysics: Conformation and dynamics of biomolecules. Hoboken: John Wiley and Sons.
Kamekawa N, Hayama K, Nakamura-Tsuruta S, Kuno A, Hirabayashi J.
2006. A combined strategy for glycan profiling: A model study
83
&
HARVEY
with pyridylaminated oligosaccharides. J Biochem (Tokyo) 140:337–
347.
Kameyama A, Kikuchi N, Nakaya S, Ito H, Sato T, Shikanai T, Takahashi Y,
Takahashi K, Narimatsu H. 2005. A Strategy for identification of
oligosaccharide structures using observational multistage mass spectral
library. Anal Chem 77:4719–4725.
Kameyama A, Nakaya S, Ito H, Kikuchi N, Angata T, Nakamura M, Ishida HK, Narimatsu H. 2006. Strategy for simulation of CID spectra of Nlinked oligosaccharides toward glycomics. J Proteome Res 5:808–814.
Kamitakahara H, Nakatsubo F. 2005. Synthesis of diblock copolymers with
cellulose derivatives. 1. Model study with azidoalkyl carboxylic acid
and cellobiosylamine derivative. Cellulose 12:209–219.
Kamitakahara H, Nakatsubo F, Klemm D. 2006. Block co-oligomers of tri-Omethylated and unmodified cello-oligosaccharides as model compounds for methylcellulose and its dissolution/gelation behavior.
Cellulose 13:375–392.
Kamiya Y, Yamaguchi Y, Takahashi N, Arata Y, Kasai K-i, Ihara Y, Matsuo I,
Ito Y, Yamamoto K, Kato K. 2005. Sugar-binding properties of VIP36,
an intracellular animal lectin operating as a cargo receptor. J Biol Chem
280:37178–37182.
Kamoda S, Ishikawa R, Kakehi K. 2006. Capillary electrophoresis with laserinduced fluorescence detection for detailed studies on N-linked
oligosaccharide profile of therapeutic recombinant monoclonal antibodies. J Chromatogr A 1133:332–339.
Kamoda S, Nakano M, Ishikawa R, Suzuki S, Kakehi K. 2005. Rapid and
sensitive screening of N-glycans as 9-fluorenylmethyl derivatives by
high-performance liquid chromatography: A method which can recover
free oligosaccharides after analysis. J Proteome Res 4:146–152.
Kanazawa A, Okumura S, Suzuki M. 2005. Powder-to-powder polycondensation of natural saccharides. Facile preparation of highly branched
polysaccharides. Org Biomol Chem 3:1746–1750.
Kanda Y, Yamane-Ohnuki N, Sakai N, Yamano K, Nakano R, Inoue M,
Misaka H, Iida S, Wakitani M, Konno Y, Yano K, Shitara K, Hosoi S,
Satoh M. 2006. Comparison of cell lines for stable production of fucosenegative antibodies with enhanced ADCC. Biotechnol Bioeng 94:680–
688.
Kandra L, Gyémánt G, Remenyik J, Ragunath C, Ramasubbu N. 2005a.
Transglycosylations catalysed by Y151M mutant of human salivary aamylase (HSA). Biologia, Bratislava 16:57–64.
Kandra L, Remenyik J, Batta G, Somsák L, Gyémánt G, Park KH. 2005b.
Enzymatic synthesis of a new inhibitor of a-amylases: Acarviosinylisomaltosyl-spiro-thiohydantoin. Carbohydr Res 340:1311–1317.
Kanekiyo K, Lee J-B, Hayashi K, Takenaka H, Hayakawa Y, Endo S, Hayashi
T. 2005. Isolation of an antiviral polysaccharide, nostoflan, from a
terrestrial cyanobacterium, Nostoc flagelliforme. J Nat Prod 68:1037–
1041.
Kaneko Y, Nimmerjahn F, Ravetch JV. 2006. Anti-inflammatory activity of
immunoglobulin G resulting from Fc sialylation. Science 313:670–
673.
Kang P, Mechref Y, Klouckova I, Novotny MV. 2005. Solid-phase
permethylation of glycans for mass spectrometric analysis. Rapid
Commun Mass Spectrom 19:3421–3428.
Kantchev B, Chang C-C, Chang D-K. 2006. Direct Fmoc/tert-Bu solid phase
synthesis of octamannosyl polylysine dendrimer-peptide conjugates.
Peptide Sci 84:232–240.
Kantchev EAB, Bader SJ, Parquette JR. 2005. Oligosaccharide synthesis on a
soluble, hyperbranched polymer support via thioglycoside activation.
Tetrahedron 61:8329–8338.
Karginov VA, Nestorovich EM, Yohannes A, Robinson TM, Fahmi NE,
Schmidtmann F, Hecht SM, Bezrukov SM. 2006a. Search for cyclodextrin-based inhibitors of anthrax toxins: Synthesis, structural
features, and relative activities. Antimicrob Agents Chemother
50:3740–3753.
84
Karginov VA, Yohannes A, Robinson TM, Fahmi NE, Alibek K, Hecht SM.
2006b. b-Cyclodextrin derivatives that inhibit anthrax lethal toxin.
Bioorg Med Chem 14:33–40.
Karnoup AS, Turkelson V, Anderson WHK. 2005. O-linked glycosylation in
maize-expressed human IgA1. Glycobiology 15:965–981.
Kasijima Y, Yamaguchi M, Hirai N, Ohmachi T, Yoshida T. 2006. In vivo
expression of UDP-N-acetylglucosamine: a-3-D-mannoside b-1,2-Nacetylglucosaminyltransferase I (GnT-1) in Aspergillus oryzae and
effects on the sugar chain of a-amylase. Biosci Biotechnol Biochem
70:2662–2668.
Kasuya MCZ, Ikeda M, Hashimoto K, Sato T. 2005a. Effect of anomeric
linkage on the sialylation of glycosides by cells. J Carbohydr Chem
24:705–715.
Kasuya MCZ, Ito A, Cusi R, Sato T, Hatanaka K. 2005b. Cellular uptake and
saccharide chain elongation of ‘‘fluoro-amphiphilic’’ glycosides. Chem
Lett 34:856–857.
Kato K, Jeanneau C, Tarp MA, Benet-Pagès A, Lorenz-Depiereux B, Bennett
EP, Mandel U, Strom TM, Clausen H. 2006. Polypeptide GalNActransferase T3 and familial tumoral calcinosis. Secretion of fibroblast
growth factor 23 requires O-glycosylation. J Biol Chem 281:18370–
18377.
Kato K, Yamaguchi Y, Takahashi N, Nishimura M, Iwamoto S-I, Sekiya S,
Tanaka K. 2004. Discrimination of isomeric fragment ions observed in
tandem mass spectra of biantennary oligosaccharides by use of selective
isotope labeling. J Mass Spectrom Soc Jpn 52:284–288.
Kaur D, Berg S, Dinadayala P, Gicquel B, Chatterjee D, McNeil MR, Vissa
VD, Crick DC, Jackson M, Brennan PJ. 2006. Biosynthesis of
mycobacterial lipoarabinomannan: Role of a branching mannosyltransferase. Proc Natl Acad Sci USA 103:13664–13669.
Kawar ZS, Haslam SM, Morris HR, Dell A, Cummings RD. 2005. Novel
poly-GalNAcb1-4GlcNAc (LacdiNAc) and fucosylated poly-LacdiNAc N-glycans from mammalian cells expressing b1,4-N-acetylgalactosaminyltransferase and a1,3-fucosyltransferase. J Biol Chem
280:12810–12819.
Kawasaki K, Ernst RK, Miller SI. 2005. Inhibition of Salmonella enterica
serovar typhimurium lipopolysaccharide deacylation by aminoarabinose membrane modification. J Bacteriol 187:2448–2457.
Kay W, Petersen BO, Duus JØ, Perry MB, Vinogradov E. 2006. Characterization of the lipopolysaccharide and b-glucan of the fish pathogen
Francisella victoria. FEBS J 273:3002–3013.
Ke W, Whitfield DM, Brisson J-R, Enright G, Jarrell HC, Wu W. 2005.
Development of specific inhibitors for heparin-binding proteins based
on the cobra cardiotoxin structure: An effective synthetic strategy for
rationally modified heparin-like disaccharides and a trisaccharide.
Carbohydr Res 340:355–372.
Keck RG, Briggs JB, Jones AJS. 2005. Oligosaccharide release and MALDITOF MS Analysis of N-Linked carbohydrate structures from glycoproteins. Methods Mol Biol 308:381–396.
Keykhosravani M, Doherty-Kirby A, Zhang C, Brewer D, Goldberg HA,
Hunter GK, Lajoie G. 2005. Comprehensive identification of posttranslational modifications of rat bone osteopontin by mass spectrometry. Biochemistry 44:6990–7003.
Kida T, Kikuzawa A, Higashimoto H, Nakatsuji Y, Akashi M. 2005. Synthesis
of novel cyclodextrin derivatives by aromatic spacer insertion and their
inclusion ability. Tetrahedron 61:5763–5768.
Kim J-H, Yang H, Khot V, Whitfield D, Boons G-J. 2006a. Stereoselective
glycosylations using (R)- or (S)-(ethoxycarbonyl)benzyl chiral auxiliaries at C-2 of glycopyranosyl donors. Eur J Org Chem:5007–5028.
Kim JH, Yang H, Park J, Boons GJ. 2005a. A general strategy for
stereoselective glycosylations. J Am Chem Soc 127:12090–12097.
Kim S-H, Jia W, Parreira VR, Bishop RE, Gyles CL. 2006b. Phosphoethanolamine substitution in the lipid A of Escherichia coli O157: H7 and its
association with PmrC. Microbiology 152:657–666.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Kim T-K, Zhang R, Feng W, Cai J, Pierce W, Song Z-H. 2005b. Expression
and characterization of human CB1 cannabinoid receptor in methylotrophic yeast Pichia pastoris. Protein Exp Purif 40:60–70.
Kim Y-G, Kim S-Y, Hur Y-M, Joo H-S, Chung J, Lee D-S, Royle L, Rudd PM,
Dwek RA, Harvey DJ, Kim B-G. 2006c. The identification and
characterization of xenoantigenic nonhuman carbohydrate sequences in
membrane proteins from porcine kidney. Proteomics 6:1133–1142.
Kislinger T, Humeny A, Peich CC, Becker CM, Pischetsrieder M. 2005.
Analysis of protein glycation products by MALDI-TOF/MS. Ann NY
Acad Sci 1043:249–259.
Kitajima T, Chiba Y, Jigami Y. 2006. Saccharomyces cerevisiae a1,6mannosyltransferase has a catalytic potential to transfer a second
mannose molecule. FEBS J 273:5074–5085.
Kiyohara M, Hama Y, Yamaguchi K, Ito M. 2006. Structure of b-1,3xylooligosaccharides generated from Caulerpa racemosa var. laetevirens b-1,3-xylan by the action of b-1,3-xylanase. J Biochem (Tokyo)
140:369–373.
Kiyonaka S, Shinkai S, Hamachi I. 2003. Combinatorial library of low
molecular-weight organo- and hydrogelators based on glycosylated
amino acid derivatives by solid-phase synthesis. Chem Eur J 9:976–
983.
Knochenmuss R. 2006. Ion formation mechanisms in UV-MALDI. Analyst
131:966–986.
Knochenmuss R, McCombie G, Faderl M. 2006. Ion yields of thin MALDI
samples: Dependence on matrix and metal substrate and implications
for models. J Phys Chem A 110:12728–12733.
Kobayashi A, Kuwata H, Kohri M, Izumi R. 2006a. A bacterial chitinase acts
as catalyst for synthesis of the N-linked oligosaccharide core
trisaccharide by employing a sugar oxazoline substrate. J Carbohydr
Chem 25:533–541.
Kobayashi S, Makino A, Matsumoto H, Kunii S, Ohmae M, Kiyosada T,
Makiguchi K, Matsumoto A, Horie M, Shoda S-I. 2006b. Enzymatic
polymerization to novel polysaccharides having a glucose-N-acetylglucosamine repeating unit, a cellulose-chitin hybrid polysaccharide.
Biomacromolecules 7:1644–1656.
Kobayashi S, Makino A, Tachibana N, Ohmae M. 2006c. Chitinase-catalyzed
synthesis of a chitin-xylan hybrid polymer: A novel water-soluble b(14) polysaccharide having an N-acetylglucosamine xylose repeating
unit. Macromol Mol Commun 27:781–786.
Kobayashi S, Ohmae M. 2006. Enzymatic polymerization of polysaccharides. Adv Polym Sci 194:159–210.
Koel M. 2005. Ionic liquids in chemical analysis. Crit Rev Anal Chem
35:177–192.
Kolarich D, Altmann F, Sunderasan E. 2006. Structural analysis of the
glycoprotein allergen Hev b 4 from natural rubber latex by mass
spectrometry. Biochim Biophys Acta 1760:715–720.
Kolarich D, Léonard R, Hemmer W, Altmann F. 2005. The N-glycans of
yellow jacket venom hyaluronidases and the protein sequence of its
major isoform in Vespula vulgaris. FEBS J 272:5182–5190.
Kolarich D, Weber A, Turecek PL, Schwarz H-P, Altmann F. 2006.
Comprehensive glyco-proteomic analysis of human a1-antitrypsin
and its charge isoforms. Proteomics 6:3369–3380.
Kondo A, Li W, Nakagawa T, Nakano M, Koyama N, Wang X, Gu J, Miyoshi
E, Taniguchi N. 2006. From glycomics to functional glycomics of sugar
chains: Identification of target proteins with functional changes using
gene targeting mice and knock down cells of FUT8 as examples.
Biochim Biophys Acta 1764:1881–1889.
Kotake T, Dina S, Konishi T, Kaneko S, Igarashi K, Samejima M, Watanabe Y,
Kimura K, Tsumuraya Y. 2005. Molecular cloning of a b-galactosidase
from radish that specifically hydrolyzes b-(1-3)- and b-(1-6)-galactosyl
residues of arabinogalactan protein. Plant Physiol 138:1563–1576.
Kovacevic S, Anderson D, Morita YS, Patterson J, Haites R, McMillan BNI,
Coppel R, McConville MJ, Billman-Jacobe H. 2006. Identification of a
Mass Spectrometry Reviews DOI 10.1002/mas
&
novel protein with a role in lipoarabinomannan biosynthesis in
mycobacteria. J Biol Chem 281:9011–9017.
Kovácik V, Bekesová S, Pätoprsty V, Rehulka P, Chmelı́k J, Kovác P. 2006.
Positive-ion fragmentation in matrix-assisted laser desorption/ionization tandem time-of-flight mass spectrometry of synthetic analogues of
the O-specific polysaccharide of Vibrio cholerae O:1. Eur J Mass
Spectrom 12:247–252.
Kovalchuk SN, Sundukova EV, Kusaykin MI, Guzev KV, Anastiuk SD,
Likhatskaya GN, Trifonov EV, Nurminski EA, Kozhemyako VB,
Zvyagintseva TN, Rasskazov VA. 2006. Purification, cDNA cloning
and homology modeling of endo-1,3-b-D-glucanase from scallop
Mizuhopecten yessoensis. Comp Biochem Physiol B 143:473–485.
Kozma K, Keusch JJ, Hegemann B, Luther KB, Klein D, Hess D, Haltiwanger
RS, Hofsteenge J. 2006. Identification and characterization of a b1,3glucosyltransferase that synthesizes the Glc-b1,3-Fuc disaccharide on
thrombospondin type 1 repeats. J Biol Chem 281:36742–36751.
Krief S, Thoison O, Sévenet T, Wrangham RW, Lavaud C. 2005. Triterpenoid
saponin anthranilates from Albizia grandibracteata leaves ingested by
primates in Uganda. J Nat Prod 68:897–903.
Kröger L, Scudlo A, Thiem J. 2006. Subsequent enzymatic galactosylation
and sialylation towards sialylated Thomsen-Friedenreich antigen
components. Adv Synth Catal 348:1217–1227.
Kubler-Kielb J, Liu T-Y, Mocca C, Majadly F, Robbins JB, Schneerson R.
2006. Additional conjugation methods and immunogenicity of Bacillus
anthracis poly-g-D-glutamic acid-protein conjugates. Infect Immun
74:4744–4749.
Kubler-Kielb J, Pozsgay V. 2005. A new method for conjugation of
carbohydrates to proteins using an aminooxy-thiol heterobifunctional
linker. J Org Chem 70:6987–6990.
Kübler-Kielb J, Vinogradov E, Garcı́a Fernández JM, Szostko B, Zwiefka A,
Gamian A. 2006. Structure and serological analysis of the Hafnia alvei
481-L O-specific polysaccharide containing phosphate in the backbone
chain. Carbohydr Res 341:2980–2985.
Kuhn J, Schnölzer M, Schön S, Müller S, Prante C, Götting C, Kleesiek K.
2005. Xylosyltransferase I acceptor properties of fibroblast growth
factor and its fragment bFGF (1-24). Biochem Biophys Res Commun
333:156–166.
Kumar ABV, Varadaraj MC, Gowda LR, Tharanathan RN. 2005. Characterization of chito-oligosaccharides prepared by chitosanolysis with the
aid of papain and pronase, and their bactericidal action against Bacillus
cereus and Escherichia coli. Biochem J 391:167–175.
Kumar NS, Pinto BM. 2005. Synthesis of D-lyxitol and D-ribitol analogues of
the naturally occurring glycosidase inhibitor salacinol. Carbohydr Res
340:2612–2619.
Kumar NS, Pinto BM. 2006. Synthesis of thioswainsonine as a potential
glycosidase inhibitor. Carbohydr Res 341:1685–1691.
Kurakake M, Sumida T, Masuda D, Oonishi S, Komaki T. 2006. Production of
galacto-manno-oligosaccharides from guar gum by b-mannanase from
Penicillium oxalicum SO. J Agric Food Chem 54:7885–7889.
Kurogochi M, Nishimura S-I. 2004. Structural characterization of Nglycopeptides by matrix-dependent selective fragmentation of
MALDI-TOF/TOF tandem mass spectrometry. Anal Chem 76:6097–
6101.
Küster B, Wheeler SF, Hunter AP, Dwek RA, Harvey DJ. 1997. Sequencing of
N-linked oligosaccharides directly from protein gels: In-gel deglycosylation followed by matrix-assisted laser desorption/ionization mass
spectrometry and normal-phase high performance liquid chromatography. Anal Biochem 250:82–101.
Kvaerno L, Werder M, Hauser H, Carreira EM. 2005. Carbohydrate sulfonyl
chlorides for simple, convenient access to glycoconjugates. Org Lett
7:1145–1148.
Kwan EM, Boraston AB, McLean BW, Kilburn DG, Warren RAJ. 2005. Nglycosidase-carbohydrate-binding module fusion proteins as immobi-
85
&
HARVEY
lized enzymes for protein deglycosylation. Protein Eng Des Sel
18:497–501.
Kwon Y-U, Soucy RL, Snyder DA, Seeberger PH. 2005. Assembly of a series
of malarial glycosylphosphatidylinositol anchor oligosaccharides.
Chem Eur J 11:2493–2504.
Kyogashima M, Tamiya-Koizumi K, Ehara T, Li G, Hu R, Hara A, Aoyama T,
Kannagi R. 2006. Rapid demonstration of diversity of sulfatide
molecular species from biological materials by MALDI-TOF MS.
Glycobiology 16:719–728.
Lam SN, Gervay-Hague J. 2005a. Glycal scavenging in the synthesis of
disaccharides using mannosyl iodide donors. J Org Chem 70:2387–
2390.
Lam SN, Gervay-Hague J. 2005b. Efficient synthesis of Man2, Man3, and
Man5 oligosaccharides, using mannosyl iodide donors. J Org Chem
70:8772–8779.
Lamidi M, Ollivier E, Mahiou V, Faure R, Debrauwer L, Ekekang LN,
Balansard G. 2005. Gluco-indole alkaloids from the bark of Nauclea
diderrichii. 1H and 13C NMR assignments of 3-5-tetrahydrodeoxycordifoline lactam and cadambine acid. Magn Reson Chem 43:427–429.
Lancaster KS, An HJ, Li B, Lebrilla CB. 2006. Interrogation of N-linked
oligosaccharides using infrared multiphoton dissociation in FT-ICR
mass spectrometry. Anal Chem 78:4990–4997.
Lapadula AJ, Hatcher PJ, Hanneman AJ, Ashline DJ, Zhang H, Reinhold VN.
2005. Congruent strategies for carbohydrate sequencing. 3. OSCAR:
An algorithm for assigning oligosaccharide topology from MSn data.
Anal Chem 77:6271–6279.
Lapolla A, Fedele D, Reitano R, Bonfante L, Guizzo M, Seraglia R, Tubaro
M, Traldi P. 2005a. Mass spectrometric study of in vivo production of
advanced glycation end-products/peptides. J Mass Spectrom 40:969–
972.
Lapolla A, Fedele D, Reitano R, Bonfante L, Pastori G, Seraglia R, Tubaro M,
Traldi P. 2005b. Advanced glycation end products/peptides: An in vivo
investigation. Ann NY Acad Sci 1043:267–275.
Lapolla A, Fedele D, Seraglia R, Traldi P. 2006. The role of mass
spectrometry in the study of non-enzymatic protein glycation in
diabetes: An update. Mass Spectrom Rev 25:775–797.
Lapolla A, Fedele D, Traldi P. 2005. Glyco-oxidation in diabetes and related
diseases. Clin Chim Acta 357:236–250.
Lapolla A, Traldi P, Fedele D. 2005. Importance of measuring products of
non-enzymatic glycation of proteins. Clin Biochem 38:103–115.
Lapolla A, Tubaro M, Fedele D, Reitano R, Arico NC, Ragazzi E, Seraglia R,
Vogliardi S, Traldi P. 2005c. A matrix-assisted laser desorption/
ionization mass spectrometry study of the non-enzymatic glycation
products of human globins in diabetes. Rapid Commun Mass Spectrom
19:162–168.
Laremore TN, Murugesan S, Park T-J, Avci FY, Zagorevski DV, Linhardt RJ.
2006. Matrix-assisted laser desorption/ionization mass spectrometric
analysis of uncomplexed highly sulfated oligosaccharides using ionic
liquid matrices. Anal Chem 78:1774–1779.
Larsen K, Thygesen MB, Guillaumie F, Willats WGT, Jensen KJ. 2006.
Solid-phase chemical tools for glycobiology. Carbohydr Res 341:
1209–1234.
Larsen MR, Højrup P, Roepstorff P. 2005. Characterization of gel-separated
glycoproteins using two-step proteolytic digestion combined with
sequential microcolumns and mass spectrometry. Mol Cell Proteomics
4:107–119.
Larsson EA, Sjöberg M, Widmalm G. 2005. Synthesis of oligosaccharides
related to the repeating unit of the capsular polysaccharide from
Streptococcus pneumoniae type 37. Carbohydr Res 340:7–13.
Laštovicková M, Chmelı́k J. 2006. Simple and fast method for recognition of
reducing and nonreducing neutral carbohydrates by matrix-assisted
laser desorption/ionization time-of-flight mass spectrometry. J Agric
Food Chem 54:5092–5097.
86
Lattová E, Kapková P, Krokhin O, Perreault H. 2006. Method for
investigation of oligosaccharides from glycopeptides: Direct determination of glycosylation sites in proteins. Anal Chem 78:2977–2984.
Lattová E, Snovida S, Perreault H, Krokhin O. 2005. Influence of the labeling
group on ionization and fragmentation of carbohydrates in mass
spectrometry. J Am Soc Mass Spectrom 16:683–696.
Laville I, Pigaglio S, Blais J-C, Doz F, Loock B, Maillard P, Grierson DS,
Blais J. 2006. Photodynamic efficiency of diethylene glycol-linked
glycoconjugated porphyrins in human retinoblastoma cells. J Med
Chem 49:2558–2567.
Lazarevic D, Thiem J. 2006. Artificial N-functionalized UDP-glucosamine
analogues as modified substrates for N-acetylglucosaminyl transferases. Carbohydr Res 341:569–576.
Le Coq J, An H-J, Lebrilla C, Viola RE. 2006. Characterization of human
aspartoacylase: The brain enzyme responsible for Canavan disease.
Biochemistry 45:5878–5884.
Le Quéré AJ-L, Deakin WJ, Schmeisser C, Carlson RW, Streit WR,
Broughton WJ, Forsberg LS. 2006. Structural characterization of a Kantigen capsular polysaccharide essential for normal symbiotic
infection in Rhizobium sp. Detection of the rkpMNO locus prevents
synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-non-ulosonic acid. J
Biol Chem 281:28981–28992.
Lee A, Wu S-W, Scherman MS, Torrelles JB, Chatterjee D, McNeil MR,
Khoo K-H. 2006a. Sequencing of oligoarabinosyl units released from
mycobacterial arabinogalactan by endogenous arabinanase: Identification of distinctive and novel structural motifs. Biochemistry 45:15817–
15828.
Lee B-S, Krishnanchettiar S, Lateef SS, Gupta S. 2005a. Characterization of
oligosaccharide moieties of glycopeptides by microwave-assisted
partial acid hydrolysis and mass spectrometry. Rapid Commun Mass
Spectrom 19:1545–1550.
Lee B-S, Krishnanchettiar S, Lateef SS, Lateef NS, Gupta S. 2005b.
Characterization of oligosaccharide moieties of intact glycoproteins by
microwave-assisted partial acid hydrolysis and mass spectrometry.
Rapid Commun Mass Spectrom 19:2629–2635.
Lee B-S, Krisnanchettiar S, Lateef SS, Lateef NS, Gupta S. 2005c.
Oligosaccharide analyses of glycopeptides of horseradish peroxidase
by thermal-assisted partial acid hydrolysis and mass spectrometry.
Carbohydr Res 340:1859–1865.
Lee D-W, Baney RH. 2004. Oligochitosan derivatives bearing electrondeficient aromatic rings for adsorption of amitriptyline: Implications for
drug detoxification. Biomacromolecules 5:1310–1315.
Lee HJ, Howell SK, Sanford RJ, Beisswenger PJ. 2005d. Methylglyoxal can
modify GAPDH activity and structure. Ann NY Acad Sci 1043:135–
145.
Lee H-S, Wolfert MA, Zhang Y, Boons G-J. 2006b. The 2-aminogluconate
isomer of Rhizobium sin-1 lipid A can antagonize TNF-production
induced by enteric LPS. ChemBioChem 7:140–148.
Lee JH, Kim Y, Ha MY, Lee EK, Choo J. 2005e. Immobilization of
aminophenylboronic acid on magnetic beads for the direct determination of glycoproteins by matrix assisted laser desorption ionization
mass spectrometry. J Am Soc Mass Spectrom 16:1456–1460.
Lee J-H, Shim JS, Lee JS, Kim M-K, Chung M-S, Kim KH. 2006c. Pectin-like
acidic polysaccharide from Panax ginseng with selective antiadhesive
activity against pathogenic bacteria. Carbohydr Res 341:1154–1163.
Lee JJ, Dissanayake S, Panico M, Morris HR, Dell A, Haslam SM. 2005f.
Mass spectrometric characterisation of Taenia crassiceps metacestode
N-glycans. Mol Biochem Parasitol 143:245–249.
Lee YJ, Lee K, Jung EH, Jeon HB, Kim KS. 2005g. Acceptor-dependent
stereoselective glycosylation: 20 -CB glycoside-mediated direct b-Darabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall. Org Lett 7:3263–3266.
Leir S-H, Parry S, Palmai-Pallag T, Evans J, Morris HR, Dell A, Harris A.
2005. Mucin glycosylation and sulphation in airway epithelial cells is
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
not influenced by cystic fibrosis transmembrane conductance regulator
expression. Am J Respir Cell Mol Biol 32:453–461.
Léonard R, Lhernould S, Carlué M, Fleurat P, Maftah A, Costa G. 2005.
Biochemical characterization of Silene alba a4-fucosyltransferase and
Lewis a products. Glycoconj J 22:71–78.
Leonard R, Petersen BO, Himly M, Kaar W, Wopfner N, Kolarich D, van-Ree
R, Ebner C, Duus JO, Ferreira F, Altmann F. 2005. Two novel types of
O-glycans on the mugwort pollen allergen Art v 1 and their role in
antibody binding. J Biol Chem 280:7932–7940.
Leonard R, Rendic D, Rabouille C, Wilson IB, Preat T, Altmann F. 2006. The
Drosophila fused lobes gene encodes an N-acetylglucosaminidase
involved in N-glycan processing. J Biol Chem 281:4867–4875.
Leone S, Molinaro A, Alfieri F, Cafaro V, Lanzetta R, Di Donato A, Parrilli M.
2006a. The biofilm matrix of Pseudomonas sp. OX1 grown on phenol is
mainly constituted by alginate oligosaccharides. Carbohydr Res
341:2456–2461.
Leone S, Molinaro A, Pessione E, Mazzoli R, Giunta C, Sturiale L, Garozzo
D, Lanzetta R, Parrilli M. 2006b. Structural elucidation of the core-lipid
A backbone from the lipopolysaccharide of Acinetobacter radioresistens S13, an organic solvent tolerant Gram-negative bacterium.
Carbohydr Res 341:582–590.
Leppänen A, Stowell SR, Blixt O, Cummings RD. 2005. Dimeric galectin-1
binds with high affinity to a2,3-sialylated and non-sialylated terminal
N-acetyllactosamine units on surface-bound extended glycans. J Biol
Chem 280:5549–5562.
Levery SB. 2005. Glycosphingolipid structural analysis and glycosphingolipidomics. Methods Enzymol 405:300–369.
Levina EV, Kalinovsky AI, Levin VS. 2006. New steroid glycosides from the
starfish Fromia milleporella. Russ J Bioorg Chem 32:84–88.
Levina EV, Kalinovsky AI, Stonik VA, Dmiternok PS, Andriyashchenko PV.
2005. Steroid compounds from Far Eastern starfishes Henricia aspera
and H. tumida. Russ J Bioorg Chem 31:467–474.
Lewandrowski U, Resemann A, Sickmann A. 2005. Laser-induced
dissociation/high-energy collision-induced dissociation fragmentation
using MALDI-TOF/TOF-MS instrumentation for the analysis of
neutral and acidic oligosaccharides. Anal Chem 77:3274–3283.
Li A, Kong F. 2005a. Concise syntheses of arabinogalactans with b-(1-6)linked galactopyranose backbones and a-(1-3)- and a-(1-2)-linked
arabinofuranose side chains. Bioorg Med Chem 13:839–853.
Li A, Kong F. 2005b. Syntheses of b-(1-6)-branched b-(1-3)-linked Dgalactans that exist in the rhizomes of Atractylodes lancea DC.
Carbohydr Res 340:1949–1962.
Li D, Roh S-A, Shim J-H, Mikami B, Baik M-Y, Park C-S, Park K-H.
2005a. Glycosylation of genistin into soluble inclusion complex form
of cyclic glucans by enzymatic modification. J Agric Food Chem
53:6516–6524.
Li H, Sethuraman N, Stadheim TA, Zha D, Prinz B, Ballew N, Bobrowicz P,
Choi B-K, Cook WJ, Cukan M, Houston-Cummings NR, Davidson R,
Gong B, Hamilton SR, Hoopes JP, Jiang Y, Kim N, Mansfield R, Nett
JH, Rios S, Strawbridge R, Wildt S, Gerngross TU. 2006. Optimization
of humanized IgGs in glycoengineered Pichia pastoris. Nat Biotechnol
24:210–215.
Li J, Du Y, Liang H. 2006. Low molecular weight water-soluble chitosans:
Preparation with the aid of cellulase, characterization, and solubility. J
Appl Polym Sci 102:1098–1105.
Li J, Du Y, Yang J, Feng T, Li A, Chen P. 2005b. Preparation and
characterisation of low molecular weight chitosan and chito-oligomers
by a commercial enzyme. Polym Degrad Stab 87:441–448.
Li JS, Li J. 2005. Characterization of N-linked oligosaccharides in
chorion peroxidase of Aedes aegypti mosquito. Protein Sci 14:2370–
2386.
Li Y, Wei G, Yu B. 2006. Aryl C-glycosylation of phenols with glycosyl
trifluoroacetimidates. Carbohydr Res 341:2717–2722.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Liang H, Tong W-Y, Zhao Y-Y, Cui J-R, Tu G-Z. 2005. An antitumor
compound julibroside J28 from Albizia julibrissin. Bioorg Med Chem
Lett 15:4493–4495.
Liberek B, Melcer A, Osuch A, Wakiec R, Milewski S, Wisniewsk A. 2005.
N-alkyl derivatives of 2-amino-2-deoxy-D-glucose. Carbohydr Res
340:1876–1884.
Lin C-C, Huang KT, Lin C-C. 2005. N-trifluoroacetyl sialyl phosphite donors
for the synthesis of a(2-9) oligosialic acids. Org Lett 7:4169–4172.
Liou H-L, Dixit SS, Xu S, Tint GS, Stock AM, Lobel P. 2006. NPC2, the
protein deficient in Niemann-Pick C2 disease, consists of multiple
glycoforms that bind a variety of sterols. J Biol Chem 281:36710–
36723.
Liparoti V, Molinaro A, Sturiale L, Garozzo D, Nazarenko EL, Gorshkova RP,
Ivanova EP, Shevcenko LS, Lanzetta R, Parrilli M. 2006. Structural
analysis of the deep rough lipopolysaccharide from Gram negative
bacterium Alteromonas macleodii ATCC 27126T: The first finding of bKdo in the inner core of lipopolysaccharides. Eur J Org Chem:4710–
4716.
Liu H, Geng M, Xin X, Li F, Zhang Z, Li J, Ding J. 2005. Multiple and
multivalent interactions of novel anti-AIDS drug candidates, sulfated
polymannuronate (SPMG)-derived oligosaccharides, with gp120 and
their anti-HIV activities. Glycobiology 15:501–510.
Liu J, Jönsson LÅ, Jiang G. 2005. Application of ionic liquids in analytical
chemistry. Trends Anal Chem 24:20–27.
Liu S, Ben RN. 2005. C-linked galactosyl serine AFGP analogues as potent
recrystallization inhibitors. Org Lett 7:2385–2388.
Liu X, Kwon Y-U, Seeberger PH. 2005. Convergent synthesis of a fully
lipidated glycosylphosphatidylinositol anchor of Plasmodium falciparum. J Am Chem Soc 127:5004–5005.
Liu X, McNally DJ, Nothaft H, Szymanski CM, Brisson J-R, Li J. 2006a.
Mass spectrometry-based glycomics strategy for exploring N-linked
glycosylation in eukaryotes and bacteria. Anal Chem 78:6081–6087.
Liu X, Stocker BL, Seeberger PH. 2006. Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis. J Am Chem Soc
128:3638–3648.
Liu Y, Ding N, Xiao H, Li Y. 2006b. Efficient syntheses of a series of
glycosphingolipids with 1,2-trans-glycosidic linkages. J Carbohydr
Chem 25:471–489.
López O, Maza S, Maya I, Fuentes J, Fernández-Bolaños JG. 2005. New
synthetic approaches to sugar ureas. Access to ureido-b-cyclodextrins.
Tetrahedron 61:9058–9069.
López-Prados J, Cuevas F, Reichardt N-C, de Paz J-L, Morales EQ, Martı́nLomas M. 2005. Design and synthesis of inositolphosphoglycan
putative insulin mediators. Org Biomol Chem 3:764–786.
López-Prados J, Martı́n-Lomas M. 2005. Inositolphosphoglycan mediators:
An effective synthesis of the conserved linear GPI anchor structure. J
Carbohydr Chem 24:393–414.
Lowe JP, Stuckey DJ, Awan FR, Jeyakumar M, Neville DCA, Platt FM,
Griffin JL, Styles P, Blamire AM, Sibson NR. 2005. MRS reveals
additional hexose N-acetyl resonances in the brain of a mouse model for
Sandhoff disease. NMR Biomed 18:517–526.
Lu J, Fraser-Reid B, Gowda C. 2005. A strategy for ready preparation of
glycolipids for multivalent presentation. Org Lett 7:3841–3843.
Lu W, Leimkuhler C, Gatto GJJ, Kruger RG, Oberthür M, Kahne D, Walsh
CT. 2005. AknT is an activating protein for the glycosyltransferase
AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin
A. Chem Biol 12:527–534.
Lucka L, Fernando M, Grunow D, Kannicht C, Horst AK, Nollau P, Wagerer
C. 2005. Identification of Lewis x structures of the cell adhesion
molecule CEACAM1 from human granulocytes. Glycobiology 15:87–
100.
Lukasiewicz J, Dzieciatkowska M, Niedziela T, Jachymek W, Augustyniuk
A, Kenne L, Lugowski C. 2006a. Complete lipopolysaccharide of
Plesiomonas shigelloides O74: H5 (strain CNCTC 144/92). 2. Lipid A,
87
&
HARVEY
its structural variability, the linkage to the core oligosaccharide, and the
biological activity of the lipopolysaccharide. Biochemistry 45:10434–
10447.
Lukasiewicz J, Niedziela T, Jachymek W, Kenne L, Lugowski C. 2006b.
Structure of the lipid A-inner core region and biological activity of
Plesiomonas shigelloides O54 (strain CNCTC 113/92) lipopolysaccharide. Glycobiology 16:538–550.
Luo Y, Ye S, Kan M, McKeehan WL. 2006a. Structural specificity in a FGF7affinity purified heparin octasaccharide required for formation of a
complex with FGF7 and FGFR2IIIb. J Cell Biochem 97:1241–1258.
Luo Y, Ye S, Kan M, McKeehan WL. 2006b. Control of fibroblast growth
factor (FGF) 7- and FGF1-induced mitogenesis and downstream
signaling by distinct heparin octasaccharide motifs. J Biol Chem
281:21052–21061.
Lütteke T, Bohne-Lang A, Loss A, Goetz T, Frank M, von der Lieth C-W.
2006. GLYCOSCIENCES.de: An Internet portal to support glycomics
and glycobiology research. Glycobiology 16:71R–81R.
Lysek R, Schütz C, Voge P. 2005. Total asymmetric synthesis of ()conduramine B-1 and of its enantiomer. N-Benzyl derivatives of
conduramine B-1 are b-glucosidase inhibitors. Bioorg Med Chem Lett
15:3071–3075.
Macrae JI, Acosta-Serrano A, Morrice NA, Mehlert A, Ferguson MA. 2005.
Structural characterization of NETNES, a novel glycoconjugate in
Trypanosoma cruzi epimastigotes. J Biol Chem 280:12201–12211.
Madsen AS, Hrdlicka PJ, Kumar TS, Wengel J. 2006. Synthesis, nucleic acid
hybridization properties and molecular modelling studies of conformationally restricted 30 -O,40 -C-methylene-linked a-L-ribonucleotides.
Carbohydr Res 341:1398–1407.
Maeda K, Mochizuki H, Watanabe M, Yashima E. 2006. Switching of
macromolecular helicity of optically active poly(phenylacetylene)s
bearing cyclodextrin pendants induced by various external stimuli. JAm
Chem Soc 128:7639–7650.
Maemura M, Ohgaki A, Nakahara Y, Hojo H, Nakahara Y. 2005. Solid-phase
synthesis of core 8 O-glycan-linked MUC5AC glycopeptide. Biosci
Biotechnol Biochem 69:1575–1583.
Maes E, Garénaux E, Strecker G, Leroy Y, Wieruszeski J-M, Brassart C,
Guérardel Y. 2005. Major O-glycans from the nest of Vespula
germanica contain phospho-ethanolamine. Carbohydr Res 340:1852–
1858.
Maillard LT, Guérineau V, Badet-Denisot M-A, Badet B, Laprévote O,
Durand P. 2006. Monitoring enzyme-catalyzed production of glucosamine-6P by matrix-assisted laser desorption/ionization time-of-flight
mass spectrometry: A new enzymatic assay for glucosamine-6P
synthase. Rapid Commun Mass Spectrom 20:666–672.
Majcherczyk PA, McKenna T, Moreillon P, Vaudaux P. 2006. The
discriminatory power of MALDI-TOF mass spectrometry to differentiate between isogenic teicoplanin-susceptible and teicoplaninresistant strains of methicillin-resistant Staphylococcus aureus. FEMS
Microbiol Lett 255:233–239.
Majumdar G, Harrington A, Hungerford J, Martinez-Hernandez A, Gerling
IC, Raghow R, Solomon S. 2006. Insulin dynamically regulates
calmodulin gene expression by sequential O-glycosylation and
phosphorylation of sp1 and its subcellular compartmentalization in
liver cells. J Biol Chem 281:3642–3650.
Makarieva TN, Denisenko VA, Dmitrenok PS, Guzii AG, Santalova EA,
Stonik VA, MacMillan JB, Molinski TF. 2005a. Oceanalin A, a hybrid
a,o-bifunctionalized sphingoid tetrahydroisoquinoline b-glycoside
from the marine sponge Oceanapia sp. Org Lett 7:2897–2900.
Makarieva TN, Guzii AG, Denisenko VA, Dmitrenok PS, Santalova EA,
Pokanevich EV, Molinski TF, Stonik VA. 2005b. Rhizochalin A, a novel
two-headed sphingolipid from the sponge Rhizochalina incrustata. J
Nat Prod 68:255–257.
Makimura Y, Watanabe S, Suzuki T, Suzuki Y, Ishida H, Kiso M, Katayama T,
Kumagai H, Yamamoto K. 2006. Chemoenzymatic synthesis and
88
application of a sialoglycopolymer with a chitosan backbone as a potent
inhibitor of human influenza virus hemagglutination. Carbohydr Res
341:1803–1808.
Makino A, Kurosaki K, Ohmae M, Kobayashi S. 2006. Chitinase-catalyzed
synthesis of alternatingly N-deacetylated chitin: A chitin-chitosan
hybrid polysaccharide. Biomacromolecules 7:950–957.
Makino A, Ohmae M, Kobayashi S. 2006. Synthesis of fluorinated chitin
derivatives via enzymatic polymerization. Macromol Biosci 6:862–
872.
Makishima S, Nozaki K, Mizuno M, Netsu E, Shinji K, Shibayama T, Kanda
T, Amano Y. 2006. Recovery of soluble sugars from waste medium for
enokitake (Flammulina velutipes) mushroom cultivation with hydrothermal reaction and enzyme digestion. J Appl Glycosci 53:261–
266.
Makita H, Nakahara Y, Fukui H, Miyanori Y, Katahira M, Srki H, Takeda M,
Koizumi J-I. 2006. Identification of 2-(cysteinyl)amido-2-deoxy-Dgalacturonic acid residue from the sheath of Leptothrix cholodnii.
Biosci Biotechnol Biochem 70:1265–1268.
Maljaars CEP, Halkes KM, de Oude WL, Haseley SR, Upton PJ, McDonnell
MB, Kamerling JP. 2006. Affinity determination of Ricinus communis
agglutinin ligands identified from combinatorial O- and S-N-glycopeptide libraries. J Comb Chem 8:812–819.
Maljaars CEP, Halkes KM, de Oude WL, van der Poel S, Pijnenburg NJM,
Kamerling JP. 2005. Preparation of S- and N-linked glycosylated amino
acid building blocks for solid-phase glycopeptide library synthesis. J
Carbohydr Chem 24:353–367.
Mandal D, Panda N, Kumar S, Banerjee S, Mandal NB, Sahu NP. 2006. A
triterpenoid saponin possessing antileishmanial activity from the leaves
of Careya arborea. Phytochemistry 67:183–190.
Mandato C, Brive L, Miura Y, Davis JA, Di-Cosmo N, Lucariello S,
Pagliardini S, Seo NS, Parenti G, Vecchione R, Freeze HH, Vajro P.
2006. Cryptogenic liver disease in four children: A novel congenital
disorder of glycosylation. Pediatr Res 59:293–298.
Mangold SL, Morgan JR, Strohmeyer GC, Gronenborn AM, Cloninger MJ.
2005. Cyanovirin-N binding to Man1-2Man functionalized dendrimers.
Org Biomol Chem 3:2354–2358.
Manimala JC, Li Z, Jain A, VedBrat S, Gildersleeve JC. 2005. Carbohydrate
array analysis of anti-Tn antibodies and lectins reveals unexpected
specificities: Implications for diagnostic and vaccine development.
ChemBioChem 6:2229–2241.
Manzoni L, Castelli R. 2006. Froc: A new fluorous protective group for
peptide and oligosaccharide synthesis. Org Lett 8:955–957.
Mares J, Müller JU, Skirgailiene A, Neumoin A, Bewley CA, Schmidt RR,
Zerbe O. 2006. A model for cell-surface-exposed carbohydrate moieties
suitable for structural studies by NMR spectroscopy. ChemBioChem
7:1764–1773.
Mariappan M, Preusser-Kunze A, Balleininger M, Eiselt N, Schmidt B,
Gande SL, Wenzel D, Dierks T, von Figura K. 2005. Expression,
localization, structural, and functional characterization of pFGE, the
paralog of the Ca-formylglycine-generating enzyme. J Biol Chem
280:15173–15179.
Marmuse L, Nepogodiev SA, Field RA. 2005a. Exploiting an aromatic
aglycone as a reporter of glycosylation stereochemistry in the synthesis
of 1,6-linked maltooligosaccharides. Tetrahedron Asym 16:477–485.
Marmuse L, Nepogodiev SA, Field RA. 2005b. ‘‘Click’’ chemistry en route to
pseudo-starch. Org Biomol Chem 3:2225–2227.
Masand G, Hanif K, Sen S, Ahsan A, Maiti S, Pasha S. 2006. Synthesis,
conformational and pharmacological studies of glycosylated chimeric
peptides of Met-enkephalin and FMRFa. Brain Res Bull 68:329–
334.
Maslen S, Sadowski P, Adam A, Lilley K, Stephens E. 2006. Differentiation
of isomeric N-glycan structures by normal-phase liquid chromatography-MALDI-TOF/TOF tandem mass spectrometry. Anal Chem
78:8491–8498.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Matsubara H, Kabuto S, Nakahara N, Ogawa T, Muramoto K, Jimbo M,
Kamiya H. 2005a. Structure and possible function of N-glycans of an
invertebrate C-type lectin from the acorn barnacle Megabalanus rosa.
Fisheries Sci 71:931–940.
Matsubara N, Oiwa K, Hohsaka T, Sadamoto R, Niikura K, Fukuhara N,
Takimoto A, Kondo H, Nishimura S-I. 2005b. Molecular design of
glycoprotein mimetics: Glycoblotting by engineered proteins with an
oxylamino-functionalized amino acid residue. Chem Eur J 11:6974–
6981.
Matsuo I, Kashiwagi T, Totani K, Ito Y. 2005. First chemical synthesis of
triglucosylated tetradecasaccharide (Glc3Man9GlcNAc2), a common
precursor of asparagine-linked oligosaccharides. Tetrahedron Lett
46:4197–4200.
Matsuo I, Totani K, Tatami A, Ito Y. 2006. Comprehensive synthesis of ER
related high-mannose-type sugar chains by convergent strategy.
Tetrahedron 62:8262–8277.
Matsuoka K, Terabatake M, Esumi Y, Hatano K, Terunuma D, Kuzuhara H.
2006. Carbosilane dendrimers bearing globotriaoses: Construction of a
series of carbosilane dendrimers bearing globotriaoses. Biomacromolecules 7:2284–2290.
Matsushita T, Hinou H, Fumoto M, Kurogochi M, Fujitani N, Shimizu H,
Nishimura S-I. 2006. Construction of highly glycosylated mucin-type
glycopeptides based on microwave-assisted solid-phase syntheses and
enzymatic modifications. J Org Chem 71:3051–3063.
Mazumder S, Lerouge P, Loutelier-Bourhis C, Driouich A, Ray B. 2005.
Structural characterisation of hemicellulosic polysaccharides from
Benincasa hispida using specific enzyme hydrolysis, ion exchange
chromatography and MALDI-TOF mass spectroscopy. Carbohydr
Polym 59:231-238.
Mazzaglia A, Forde D, Garozzo D, Malvagna P, Ravoo BJ, Darcy R. 2004.
Multivalent binding of galactosylated cyclodextrin vesicles to lectin.
Org Biomol Chem 2:957–960.
Mechref Y, Kang P, Novotny MV. 2006. Differentiating structural isomers of
sialylated glycans by matrix-assisted laser desorption/ionization timeof-flight/time-of-flight tandem mass spectrometry. Rapid Commun
Mass Spectrom 20:1381–1389.
Mechref Y, Muzikar J, Novotny MV. 2005. Comprehensive assessment of Nglycans derived from a murine monoclonal antibody: A case for
multimethodological approach. Electrophoresis 26:2034–2046.
Mechref Y, Novotny MV. 2006. Miniaturized separation techniques in
glycomic investigations. J Chromatogr B 841:65–78.
Medzihradszky KF. 2005. Characterization of protein N-glycosylation.
Methods Enzymol 405:116–138.
Mehlmann M, Garvin AM, Steinwand M, Gauglitz G. 2005. Reflectometric
interference spectroscopy combined with MALDI–TOF mass spectrometry to determine quantitative and qualitative binding of mixtures
of vancomycin derivatives. Anal Bioanal Chem 382:1942–1948.
Mehra R, Kelly P. 2006. Milk oligosaccharides: Structural and technological
aspects. Int Dairy J 16:1334–1340.
Mehta AS, Saile E, Zhong W, Buskas T, Carlson R, Kannenberg E, Reed Y,
Quinn CP, Boons G-J. 2006. Synthesis and antigenic analysis of the
BclA glycoprotein oligosaccharide from the Bacillus anthracis
exosporium. Chem Eur J 12:9136–9149.
Melander C, Adden R, Brinkmalm G, Gorton L, Mischnick P. 2006. New
approaches to the analysis of enzymatically hydrolyzed methyl
cellulose. Part 2. Comparison of various enzyme preparations.
Biomacromolecules 7:1410–1421.
Mennella C, Visciano M, Napolitano A, Del-Castillo MD, Fogliano V.
2006. Glycation of lysine-containing dipeptides. J Peptide Sci 12:291–
296.
Menon KN, Ikeda T, Fujimoto I, Narimatsu H, Nakakita S-I, Hase S, Ikenaka
K. 2005. Changes in N-linked sugar chain patterns induced by
moderate-to-high expression of the galactosyltransferase I gene in a
brain-derived cell line, CG4. J Neurosci Res 80:29–36.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Mesaros M, Tarzi OI, Erra-Balsells R, Bilmes GM. 2006. The photophysics of
some UV-MALDI matrices studied by using spectroscopic, photoacoustic and luminescence techniques. Chem Phys Lett 426:334–340.
Meyer S, van-Liempt E, Imberty A, van-Kooyk Y, Geyer H, Geyer R, van-Die
I. 2005. DC-SIGN mediates binding of dendritic cells to authentic
pseudo-LewisY glycolipids of Schistosoma mansoni cercariae, the first
parasite-specific ligand of DC-SIGN. J Biol Chem 280:37349–37359.
Mills K, Eaton S, Ledger V, Young E, Winchester B. 2005. The synthesis of
internal standards for the quantitative determination of sphingolipids by
tandem mass spectrometry. Rapid Commun Mass Spectrom 19:1739–
1748.
Mills K, Mills P, Jackson M, Worthington V, Beesley C, Mann A, Clayton P,
Grunewald S, Keir G, Young L, Langridge J, Mian N, Winchester B.
2006. Diagnosis of congenital disorders of glycosylation type-I using
protein chip technology. Proteomics 6:2295–2304.
Minamisawa T, Suzuki K, Hirabayashi J. 2006. Systematic identification of
N-acetylheparosan oligosaccharides by tandem mass spectrometric
fragmentation. Rapid Commun Mass Spectrom 20:267–274.
Minamisawa T, Suzuki K, Kajimoto N, Iida M, Maeda H, Hirabayashi J. 2006.
Microscale preparation of even- and odd-numbered N-acetylheparosan
oligosaccharides. Carbohydr Res 341:230–237.
Miura T, Tsujino S, Satoh A, Goto K, Mizuno M, Noguchi M, Kajimoto T,
Node M, Murakami Y, Imai N, Inazu T. 2005a. Fluorescence
modification of Gb3 oligosaccharide and rapid synthesis of oligosaccharide moieties using fluorous protective group. Tetrahedron
61:6518–6526.
Miura Y, Tay SKH, Aw MM, Eklund EA, Freeze HH. 2005b. Clinical and
biochemical characterization of a patient with congenital disorder of
glycosylation (CDG) IIx. J Pediatr 147:851–853.
Miyamoto Y, Mukai T, Nakata N, Maeda Y, Kai M, Naka T, Yano I, Makino
M. 2006. Identification and characterization of the genes involved in
glycosylation pathways of mycobacterial glycopeptidolipid biosynthesis. J Bacteriol 188:86–95.
Miyata S, Sato C, Kumita H, Toriyama M, Vacquier VD, Kitajima K. 2006.
Flagellasialin: A novel sulfated a2,9-linked polysialic acid glycoprotein of sea urchin sperm flagella. Glycobiology 16:1229–1241.
Miyauchi M, Hoshino T, Yamaguchi H, Kamitori S, Harada A. 2005. A
[2]rotaxane capped by a cyclodextrin and a guest: Formation of
supramolecular [2]rotaxane polymer. J Am Chem Soc 127:2034–2035.
Miyazawa T, Funazukuri T. 2005. Polysaccharide hydrolysis accelerated by
adding carbon dioxide under hydrothermal conditions. Biotechnol Prog
21:1782–1785.
Miyazawa T, Funazukuri T. 2006. Noncatalytic hydrolysis of guar gum under
hydrothermal conditions. Carbohydr Res 341:870–877.
Mizuno M, Goto K, Miura T. 2005. Fluorous glycopeptide synthesis without
protection of sugar hydroxy groups. Chem Lett 34:426–427.
Mizuno M, Goto K, Miura T, Inazu T. 2006a. Rapid oligosaccharide and
peptide syntheses on a recyclable fluorous support. QSAR Comb Sci
25:742–752.
Mizuno M, Matsumoto H, Goto K, Hamasaki K. 2006b. Synthesis of
aminoglycoside derivatives on a Cbz-type heavy fluorous tag.
Tetrahedron Lett 47:8831–8835.
Moe GR, Dave A, Granoff DM. 2005. Epitopes recognized by a nonautoreactive murine anti-N-propionyl meningococcal group B polysaccharide monoclonal antibody. Infect Immun 73:2123–2128.
Mohamed HE, van de Meene AML, Roberson RW, Vermaas WFJ. 2005.
Myxoxanthophyll is required for normal cell wall structure and
thylakoid organization in the cyanobacterium Synechocystis sp. strain
PCC 6803. J Bacteriol 187:6883–6892.
Mohand FA, Farkaš V. 2006. Screening for hetero-transglycosylating
activities in extracts from nasturtium (Tropaeolum majus). Carbohydr
Res 341:577–581.
Momcilovic D, Schagerlöf H, Wittgren B, Wahlund K-G, Brinkmalm G.
2005a. Improved chemical analysis of cellulose ethers using dialkyl-
89
&
HARVEY
amine derivatization and mass spectrometry. Biomacromolecules
6:2793–2799.
Momcilovic D, Wahlund K-G, Wittgren B, Brinkmalm G. 2005b. Improved
matrix-assisted laser desorption/ionisation sample preparation of a
partially depolymerised cellulose derivative by continuous spray
deposition and interfacing with size-exclusion chromatography. Rapid
Commun Mass Spectrom 19:947–954.
Monk CR, Sutton-Smith M, Dell A, Garden OA. 2006. Preparation of CD25þ
and CD25 CD4þ T cells for glycomic analysis—A cautionary tale of
serum glycoprotein sequestration. Glycobiology 16:11G–13G.
Montoya-Peleaz PJ, Riley JG, Szarek WA, Valvano MA, Schutzbach JS,
Brockhausen I. 2005. Identification of a UDP-Gal: GlcNAc-R
galactosyltransferase activity in Escherichia coli VW187. Bioorg
Med Chem Lett 15:1205–1211.
Moon Y-H, Kim G, Lee J-H, Jin X-J, Kim D-W, Kim D. 2006. Enzymatic
synthesis and characterization of novel epigallocatechin gallate glucosides. J Mol Catal B Enzym 40:1–7.
Moore JP, Nguema-Ona E, Chevalier L, Lindsey GG, Brandt WF, Lerouge P,
Farrant JM, Driouich A. 2006. Response of the leaf cell wall to
desiccation in the resurrection plant Myrothamnus flabellifolius. Plant
Physiol 141:651–662.
Moraes G, Northcote PT, Silchenko AS, Antonov AS, Kalinovsky AI,
Dmitrenok PS, Avilov SA, Kalinin VI, Stonik VA. 2005. Mollisosides
A, B1, and B2: Minor triterpene glycosides from the New Zealand and
South Australian sea cucumber Australostichopus mollis. J Nat Prod
68:842–847.
Morales V, Sanz ML, Olano A, Corzo N. 2006. Rapid separation on activated
charcoal of high oligosaccharides in honey. Chromatographia 64:233–
238.
Morelle W, Canis K, Chirat F, Faid V, Michalski J-C. 2006a. The use of mass
spectrometry for the proteomic analysis of glycosylation. Proteomics
6:3993–4015.
Morelle W, Donadio S, Ronin C, Michalski J-C. 2006b. Characterization of Nglycans of recombinant human thyrotropin using mass spectrometry.
Rapid Commun Mass Spectrom 20:331–345.
Morelle W, Flahaut C, Michalski J-C, Louvet A, Mathurin P, Klein A. 2006c.
Mass spectrometric approach for screening modifications of total serum
N-glycome in human diseases: Application to cirrhosis. Glycobiology
16:281–293.
Morelle W, Jimenez JC, Cieniewski-Bernard C, Dei-Cas E, Michalski JC.
2005a. Characterization of the N-linked glycans of Giardia intestinalis.
Glycobiology 15:549–559.
Morelle W, Michalski J-C. 2005. The mass spectrometric analysis of
glycoproteins and their glycan structures. Curr Anal Chem 1:29–57.
Morelle W, Slomianny M-C, Diemer H, Schaeffer C, van Dorsselaer A,
Michalski J-C. 2005b. Structural characterization of 2-aminobenzamide-derivatized oligosaccharides using a matrix-assisted laser
desorption/ionization two-stage time-of-flight tandem mass spectrometer. Rapid Commun Mass Spectrom 19:2075–2084.
Morgan JR, Cloninger MJ. 2005. Synthesis of carbohydrate-linked poly(polyoxometalate) poly(amido)amine dendrimers. J Polym Sci A 43:
3059–3066.
Morinaga O, Tanaka H, Shoyama Y. 2006. Detection and quantification of
ginsenoside Re in ginseng samples by a chromatographic immunostaining method using monoclonal antibody against ginsenoside Re. J
Chromatogr B 830:100–104.
Morita YS, Sena CBC, Waller RF, Kurokawa K, Sernee MF, Nakatani F,
Haites RE, Billman-Jacobe H, McConville MJ, Maeda Y, Kinoshita T.
2006. PimE is a polyprenol-phosphate-mannose-dependent mannosyltransferase that transfers the fifth mannose of phosphatidylinositol
mannoside in mycobacteria. J Biol Chem 281:25143–25155.
Morón B, Soria-Dı́az ME, Ault J, Verroios G, Noreen S, Rodrı́guez-Navarro
DN, Gil-Serrano A, Thomas-Oates J, Megı́as M, Sousa C. 2005. Low
90
pH changes the profile of nodulation factors produced by Rhizobium
tropici CIAT899. Chem Biol 12:1029–1040.
Moscatiello R, Mariani P, Sanders D, Maathuis FJM. 2006. Transcriptional
analysis of calcium-dependent and calcium-independent signalling
pathways induced by oligogalacturonides. J Exp Bot 57:2847–2865.
Mouille G, Witucka-Wall H, Bruyant M-P, Loudet O, Pelletier S, Rihouey C,
Lerouxel O, Lerouge P, Höfte H, Pauly M. 2006. Quantitative trait loci
analysis of primary cell wall composition in Arabidopsis. Plant Physiol
141:1035–1044.
Mouyna I, Morelle W, Vai M, Monod M, Léchenne B, Fontaine T, Beauvais A,
Sarfati J, Prévost M-C, Henry C, Latgé J-P. 2005. Deletion of GEL2
encoding for a b(1–3)glucanosyltransferase affects morphogenesis and
virulence in Aspergillus fumigatus. Mol Microbiol 56:1675–1688.
Mukherjee R, Gomez M, Jayaraman N, Smith I, Chatterji D. 2005.
Hyperglycosylation of glycopeptidolipid of Mycobacterium smegmatis
under nutrient starvation: Structural studies. Microbiology 151:2385–
2392.
Müllegger JM, Chen HM, Warren RAJ, Withers SG. 2006. Glycosylation of a
neoglycoprotein by using glycosynthase and thioglycoligase
approaches: The generation of a thioglycoprotein. Angew Chem Int
Ed Engl 45:2585–2588.
Müller R, Allmaier G. 2006. Molecular weight determination of ultra-high
mass compounds on a standard matrix-assisted laser desorption/
ionization time-of-flight mass spectrometer: PAMAM dendrimer
generation 10 and immunoglobulin M. Rapid Commun Mass Spectrom
20:3803–3806.
Murayama T, Tanabe T, Ikeda H, Ueno A. 2006. Direct assay for a-amylase
using fluorophore-modified cyclodextrins. Bioorg Med Chem
14:3691–3696.
Murozuka Y, Kasuya MCZ, Kobayashi M, Watanabe Y, Sato T, Hatanaka K.
2005. Efficient sialylation on azidododecyl lactosides by using B16
melanoma cells. Chem Biodiversity 2:1063–1078.
Murphy RC, Raetz CRH, Reynolds CM, Barkley RM. 2005. Mass
spectrometry advances in lipidomica: Collision-induced decomposition
of Kdo2 –lipid A. Prostaglandins 77:131–140.
Muthukrishnan S, Jutz G, André X, Mori H, Müller AHE. 2005. Synthesis of
hyperbranched glycopolymers via self-condensing atom transfer
radical copolymerization of a sugar-carrying acrylate. Macromolecules
38:9–18.
Muthukrishnan S, Mori H, Müller AHE. 2005. Synthesis and characterization
of methacrylate-type hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization. Macromolecules 38:3108–
3119.
Muzitano MF, Tinoco LW, Guette C, Kaiser CR, Rossi-Bergmann B, Costa
SS. 2006. The antileishmanial activity assessment of unusual flavonoids
from Kalanchoe pinnata. Phytochemistry 67:2071–2077.
Nagahori N, Nishimura S-I. 2006. Direct and efficient monitoring of
glycosyltransferase reactions on gold colloidal nanoparticles by using
mass spectrometry. Chem Eur J 12:6478–6485.
Nagaike F, Onuma Y, Kanazawa C, Hojo H, Ueki A, Nakahara Y, Nakahara Y.
2006. Efficient microwave-assisted tandem N- to S-acyl transfer and
thioester exchange for the preparation of a glycosylated peptide
thioester. Org Lett 8:4465–4468.
Naka R, Kamoda S, Ishizuka A, Kinoshita M, Kakehi K. 2006. Analysis of
total N-glycans in cell membrane fractions of cancer cells using a
combination of serotonin affinity chromatography and normal phase
chromatography. J Proteome Res 5:88–97.
Nakagawa T, Uozumi N, Nakano M, Mizuno-Horikawa Y, Okuyama N,
Taguchi T, Gu J, Kondo A, Taniguchi N, Miyoshi E. 2006. Fucosylation
of N-glycans regulates the secretion of hepatic glycoproteins into bile
ducts. J Biol Chem 281:29797–29806.
Nakajima K, Kinoshita M, Matsushita N, Urashima T, Suzuki M, Suzuki A,
Kakehi K. 2006. Capillary affinity electrophoresis using lectins for the
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
analysis of milk oligosaccharide structure and its application to bovine
colostrum oligosaccharides. Anal Biochem 348:105–114.
Nakamura K, Suzuki Y, Goto-Inoue N, Yoshida-Noro C, Suzuki A. 2006.
Structural characterization of neutral glycosphingolipids by thin-layer
chromatography coupled to matrix-assisted laser desorption/ionization
quadrupole ion trap time-of-flight MS/MS. Anal Chem 78:5736–5743.
Nakamura S, Yagi F, Totani K, Ito Y, Hirabayashi J. 2005. Comparative
analysis of carbohydrate-binding properties of two tandem repeat-type
Jacalin-related lectins, Castanea crenata agglutinin and Cycas revoluta
leaf lectin. FEBS J 272:2784–2799.
Nakano H, Shizuma M, Murakami H, Kiryu T, Kiso T. 2005. One-pot
synthesis of glycosyl poly(arbutin) by enzymatic glycosylation
followed by polymerization with peroxidase. J Mol Catal B Enzym
33:1–8.
Naruchi K, Hamamoto T, Kurogochi M, Hinou H, Shimizu H, Matsushita T,
Fujitani N, Kondo H, Nishimura S-I. 2006. Construction and structural
characterization of versatile lactosaminoglycan-related compound
library for the synthesis of complex glycopeptides and glycosphingolipids. J Org Chem 71:9609–9621.
Nasi R, Pinto BM. 2006. Synthesis of new analogues of salacinol containing a
pendant hydroxymethyl group as potential glycosidase inhibitors.
Carbohydr Res 341:2305–2311.
Natalello A, Ami D, Brocca S, Lotti M, Doglia SM. 2005. Secondary
structure, conformational stability and glycosylation of a recombinant
Candida rugosa lipase studied by Fourier-transform infrared spectroscopy. Biochem J 385:511–517.
Nergard CS, Kiyohara H, Reynolds JC, Thomas-Oates JE, Matsumoto T,
Yamada H, Michaelsen TE, Diallo D, Paulsen BS. 2005. Structureimmunomodulating activity relationships of a pectic arabinogalactan
from Vernonia kotschyana Sch. Bip. ex Walp. Carbohydr Res
340:1789–1801.
Nergard CS, Kiyohara H, Reynolds JC, Thomas-Oates JE, Matsumoto T,
Yamada H, Patel T, Petersen D, Michaelsen TE, Diallo D, Paulsen BS.
2006. Structures and structure-activity relationships of three mitogenic
and complement fixing pectic arabinogalactans from the Malian
antiulcer plants Cochlospermum tinctorium A. Rich and Vernonia
kotschyana Sch. Bip. ex Walp. Biomacromolecules 7:71–79.
Neubacher B, Schmidt D, Ziegelmüller P, Thiem J. 2005. Preparation of
sialylated oligosaccharides employing recombinant trans-sialidase
from Trypanosoma cruzi. Org Biomol Chem 3:1551–1556.
Neuhof T, Schmieder P, Seibold M, Preussel K, von Döhren H. 2006.
Hassallidin B—Second antifungal member of the Hassallidin family.
Bioorg Med Chem Lett 16:4220–4222.
Ngantung FA, Miller PG, Brushett FR, Tang GL, Wang DI. 2006. RNA
interference of sialidase improves glycoprotein sialic acid content
consistency. Biotechnol Bioeng 95:106–119.
Nguema-Ona E, Andème-Onzighi C, Aboughe-Angone S, Bardor M, Ishii T,
Lerouge P, Driouich A. 2006. The reb 1-1 mutation of Arabidopsis.
Effect on the structure and localization of galactose-containing cell wall
polysaccharides. Plant Physiol 140:1406–1417.
Niedziela T, Dag S, Lukasiewicz J, Dzieciatkowska M, Jachymek W,
Lugowski C, Kenne L. 2006. Complete lipopolysaccharide of
Plesiomonas shigelloides O74: H5 (strain CNCTC 144/92). 1.
Structural analysis of the highly hydrophobic lipopolysaccharide,
including the O-antigen, its biological repeating unit, the core
oligosaccharide, and the linkage between them. Biochemistry
45:10422–10433.
Niedziela T, Letowska I, Lukasiewicz J, Kaszowska M, Czarnecka A, Kenne
L, Lugowski C. 2005. Epitope of the vaccine-type Bordetella pertussis
strain 186 lipooligosaccharide and antiendotoxin activity of antibodies
directed against the terminal pentasaccharide-tetanus toxoid conjugate.
Infect Immun 73:7381–7389.
Niikura K, Kamitani R, Kurogochi M, Uematsu R, Shinohara Y, Nakagawa H,
Deguchi K, Monde K, Kondo H, Nishimura S. 2005. Versatile
Mass Spectrometry Reviews DOI 10.1002/mas
&
glycoblotting nanoparticles for high-throughput protein glycomics.
Chem Eur J 11:3825–3834.
Ninonuevo MR, Park Y, Yin H, Zhang J, Ward RE, Clowers BH, German JB,
Freeman SL, Killeen K, Grimm R, Lebrilla CB. 2006. A strategy for
annotating the human milk glycome. J Agric Food Chem 54:7471–
7480.
Nishimura S-I, Niikura K, Kurogochi M, Matsushita T, Fumoto M, Hinou H,
Kamitani R, Nakagawa H, Deguchi K, Miura N, Monde K, Kondo H.
2005. High-throughput protein glycomics: Combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry.
Angew Chem Int Ed Engl 44:91–96.
Niwa T. 2006. Mass spectrometry for the study of protein glycation in disease.
Mass Spectrom Rev 25:713–723.
Nokami T, Werz DB, Seeberger PH. 2005. Synthesis and reactions of 1,4anhydrogalactopyranose and 1,4-anhydroarabinose—Steric and electronic limitations. Helv Chim Acta 88:2823–2831.
Nolen EG, Kurish AJ, Potter JM, Donahue LA, Orlando MD. 2005.
Stereoselective synthesis of a-C-glucosyl serine and alanine via a crossmetathesis/cyclization strategy. Org Lett 7:3383–3386.
North SJ, Koles K, Hembd C, Morris HR, Dell A, Panin VM, Haslam SM.
2006. Glycomic studies of Drosophila melanogaster embryos.
Glycoconj J 23:345–354.
Novotny MV, Mechref Y. 2005. New hyphenated methodologies in highsensitivity glycoprotein analysis. J Sep Sci 28:1956–1968.
Numata M, Ikeda A, Shinkai S. 2000. Properly assembled dendrons can be
immobilized into dendrimers by in situ cross-link. Chem Lett 29:370–
371.
O’Connor ET, Piekarowicz A, Swanson KV, Griffiss JM, Stein DC. 2006.
Biochemical analysis of Lpt3, a protein responsible for phosphoethanolamine addition to lipooligosaccharide of pathogenic Neisseria. J
Bacteriol 188:1039–1048.
Oguri S, Yoshida A, Minowa MT, Takeuchi M. 2006. Kinetic properties and
substrate specificities of two recombinant human N-acetylglucosaminyltransferase-IV isozymes. Glycoconj J 23:473–480.
Ohga K, Takashima Y, Takahashi H, Kawaguchi Y, Yamaguchi H, Harada A.
2005. Preparation of supramolecular polymers from a cyclodextrin
dimer and ditopic guest molecules: Control of structure by linker
flexibility. Macromolecules 38:5897–5904.
Ojima N, Masuda K, Tanaka K, Nishimura O. 2005. Analysis of neutral
oligosaccharides for structural characterization by matrix-assisted laser
desorption/ionization quadrupole ion trap time-of-flight mass spectrometry. J Mass Spectrom 40:380–388.
Okada H, Fukushi E, Yamamori A, Kawazoe N, Onodera S, Kawabata J,
Shiomi N. 2006. Structural analysis of a novel saccharide isolated from
fermented beverage of plant extract. Carbohydr Res 341:925–929.
Okuyama M, Tanimoto Y, Ito T, Anzai A, Mori H, Kimura A, Matsui H, Chiba
S. 2005. Purification and characterization of the hyper-glycosylated
extracellular a-glucosidase from Schizosaccharomyces pombe. Enzyme
Microb Technol 37:472–480.
Okuyama N, Ide Y, Nakano M, Nakagawa T, Yamanaka K, Moriwaki K,
Murata K, Ohigashi H, Yokoyama S, Eguchi H, Ishikawa O, Ito T, Kato
M, Kasahara A, Kawano S, Gu J, Taniguchi N, Miyoshi E. 2006.
Fucosylated haptoglobin is a novel marker for pancreatic cancer: A
detailed analysis of the oligosaccharide structure and a possible
mechanism for fucosylation. Int J Cancer 118:2803–2808.
Omaetxebarria MJ, Hägglund P, Elortza F, Hooper NM, Arizmendi JM,
Jensen ON. 2006. Isolation and characterization of glycosylphosphatidylinositol-anchored peptides by hydrophilic interaction chromatography and MALDI tandem mass spectrometry. Anal Chem 78:3335–
3341.
Omtvedt LA, Royle L, Husby G, Sletten K, Radcliffe CM, Harvey DJ, Dwek
RA, Rudd PM. 2006. The glycan analysis of monoclonal
antibodies secreted in deposition disorders indicates that subsets of
91
&
HARVEY
plasma cells differentially process IgG glycans. Arthritis Rheum
54:3433–3440.
Onodera K-i, Hanashiro K, Yasumoto T. 2006. Camellianoside, a novel
antioxidant glycoside from the leaves of Camellia japonica. Biosci
Biotechnol Biochem 70:1995–1998.
O’Reilly MK, Zhang G, Imperiali B. 2006. In vitro evidence for the dual
function of Alg2 and Alg11: Essential mannosyltransferases in Nlinked glycoprotein biosynthesis. Biochemistry 45:9593–9603.
Ortega-Caballero F, Bjerre J, Laustsen LS, Bols M. 2005. Four orders of
magnitude rate increase in artificial enzyme-catalyzed aryl glycoside
hydrolysis. J Org Chem 70:7217–7226.
Oscarson S, Sehgelmeble FW. 2005. A stereoselective approach to
phosphodiester-linked oligomers of the repeating unit of Escherichia
coli K52 capsular polysaccharide containing b-D-fructofuranosyl
moieties. Tetrahedron Asym 16:121–125.
Ostendorp T, Weibel M, Leclerc E, Kleinert P, Kroneck PMH, Heizmann CW,
Fritz G. 2006. Expression and purification of the soluble isoform of
human receptor for advanced glycation end products (sRAGE) from
Pichia pastoris. Biochem Biophys Res Commun 347:4–11.
Otto VI, Damoc E, Cueni LN, Schürpf T, Frei R, Ali S, Callewaert N, Moise
A, Leary JA, Folkers G, Przybylski M. 2006. N-glycan structures and Nglycosylation sites of mouse soluble intercellular adhesion molecule-1
revealed by MALDI-TOF and FTICR mass spectrometry. Glycobiology
16:1033–1044.
Pabba J, Mohal N, Vasella A. 2006. Synthesis of glucuronic, mannuronic, and
galacturonic acid-derived imidazoles as inhibitors of bovine liver bglucuronidase. Helv Chim Acta 89:1373–1386.
Palm AK, Novotny MV. 2005. A monolithic PNGase F enzyme microreactor
enabling glycan mass mapping of glycoproteins by mass spectrometry.
Rapid Commun Mass Spectrom 19:1730–1738.
Palm M, Zacchi G. 2003. Extraction of hemicellulosic oligosaccharides from
spruce using microwave oven or steam treatment. Biomacromolecules
4:617–623.
Pan C, Xu S, Hu L, Su X, Ou J, Zou H, Guo Z, Zhang Y, Guo B. 2005. Using
oxidized carbon nanotubes as matrix for analysis of small molecules by
MALDI-TOF MS. J Am Soc Mass Spectrom 16:883–892.
Paramonov N, Rangarajan M, Hashim A, Gallagher A, Aduse-Opoku J,
Slaney JM, Hounsell E, Curtis MA. 2005. Structural analysis of a novel
anionic polysaccharide from Porphyromonas gingivalis strain W50
related to Arg-gingipain glycans. Mol Microbiol 58:847–863.
Park H, Choi Y, Kang S, Lee S, Kwon C, Jung S. 2006. pH-dependent
inclusion complexation of carboxymethylated cyclosophoraoses to Nacetylphenylalanine. Carbohydr Polym 64:85–91.
Park JK, Khan T, Jung JY. 2006. Structural studies of the glucuronic acid
oligomers produced by Gluconacetobacter hansenii strain. Carbohydr
Polym 63:482–486.
Park N-Y, Baek N-I, Cha J, Lee S-B, Auh J-H, Park C-S. 2005a. Production of
a new sucrose derivative by transglycosylation of recombinant
Sulfolobus shibatae b-glycosidase. Carbohydr Res 340:1089–1096.
Park T-H, Choi K-W, Park C-S, Lee S-B, Kang H-Y, Shon K-J, Park J-S, Cha J.
2005b. Substrate specificity and transglycosylation catalyzed by a
thermostable b-glucosidase from marine hyperthermophile Thermotoga neapolitana. Appl Microbiol Biotechnol 69:411–422.
Parry S, Hadaschik D, Blancher C, Kumaran MK, Bochkina N, Morris HR,
Richardson S, Aitman TJ, Gauguier D, Siddle K, Scott J, Dell A. 2006a.
Glycomics investigation into insulin action. Biochim Biophys Acta
1760:652–668.
Parry S, Hanisch FG, Leir S-H, Sutton-Smith M, Morris HR, Dell A, Harris A.
2006b. N-glycosylation of the MUC1 mucin in epithelial cells
and secretions. Glycobiology 16:623–634.
Paschinger K, Hackl M, Gutternigg M, Kretschmer-Lubich D, Stemmer U,
Jantsch V, Lochnit G, Wilson IB. 2006. A deletion in the golgi alphamannosidase II gene of Caenorhabditis elegans results in unexpected
non-wild-type N-glycan structures. J Biol Chem 281:28265–28277.
92
Paschinger K, Staudacher E, Stemmer U, Fabini G, Wilson IBH. 2005.
Fucosyltransferase substrate specificity and the order of fucosylation in
invertebrates. Glycobiology 15:463–474.
Patel A, Lindhorst TK. 2006. Multivalent glycomimetics: Synthesis of
nonavalent mannoside clusters with variation of spacer properties.
Carbohydr Res 341:1657–1668.
Pedersen NR, Kristensen JB, Bauw G, Ravoo BJ, Darcy R, Larsen KL,
Pedersen LH. 2005. Thermolysin catalyses the synthesis of cyclodextrin
esters in DMSO. Tetrahedron Asym 16:615–622.
Pérez S, Mulloy B. 2005. Prospects for glycoinformatics. Curr Opin Struct
Biol 15:517–524.
Pérez-Balderas F, Hernández-Mateo F, Santoyo-González F. 2005. Synthesis
of multivalent neoglycoconjugates by 1,3 dipolar cycloaddition of
nitrile oxides and alkynes and evaluation of their lectin-binding
affinities. Tetrahedron 61:9338–9348.
Peri F, Marinzi C, Barath M, Granucci F, Urbano M, Nicotra F. 2006.
Synthesis and biological evaluation of novel lipid A antagonists. Bioorg
Med Chem 14:190–199.
Peri F, Nicotra F, Leslie CP, Micheli F, Seneci P, Marchioro C. 2003. Dglucose as a regioselectively addressable scaffold for combinatorial
chemistry on solid phase. J Carbohydr Chem 22:57–71.
Péroche S, Degobert G, Putaux J-L, Blanchin M-G, Fessi H, Parrot-Lopez H.
2005. Synthesis and characterisation of novel nanospheres made from
amphiphilic perfluoroalkylthio-b-cyclodextrins. Eur J Pharm Biopharm
60:123–131.
Perrone A, Plaza A, Bloise E, Nigro P, Hamed AI, Belisario MA, Pizza
C, Piacente S. 2005. Cytotoxic furostanol saponins and a megastigmane glucoside from Tribulus parvispinus. J Nat Prod 68:1549–
1553.
Peter-Katalinic J. 2005. O-glycosylation of proteins. Methods Enzymol
405:139–171.
Petruccelli S, Otegui MS, Lareu F, Dinh OT, Fitchette A-C, Circosta A,
Rumbo M, Bardor M, Carcamo R, Gomord V, Beachy RN. 2006. A
KDEL-tagged monoclonal antibody is efficiently retained in the
endoplasmic reticulum in leaves, but is both partially secreted and
sorted to protein storage vacuoles in seeds. Plant Biotechnol J 4:511–
527.
Pinto MR, Gorin PAJ, Wait R, Mulloy B, Barreto-Bergter E. 2005. Structures
of the O-linked oligosaccharides of a complex glycoconjugate from
Pseudallescheria boydii. Glycobiology 15:895–904.
Plaza A, Perrone A, Balestrieri C, Balestrieri ML, Bifulco G, Carbone V,
Hamed A, Pizza C, Piacente S. 2005a. New antiproliferative 14,15secopregnane glycosides from Solenostemma argel. Tetrahedron 61:
7470–7480.
Plaza A, Perrone A, Balestrieri ML, Felice F, Balestrieri C, Hamed AI, Pizza
C, Piacente S. 2005b. New unusual pregnane glycosides with
antiproliferative activity from Solenostemma argel. Steroids 70:594–
603.
Pochec E, Litynska A, Bubka M, Amoresano A, Casbarra A. 2006.
Characterization of the oligosaccharide component of a3b1 integrin
from human bladder carcinoma cell line T24 and its role in adhesion and
migration. Eur J Cell Biol 85:47–57.
Pojasek K, Raman R, Sasisekharan R. 2005. Structural characterization of
glycosaminoglycans. In: Yarema KJ, editor. Handbook of Carbohydrate
Engineering. Boca Raton, FL: Taylor and Francis. pp 177–210.
Powell AK, Harvey DJ. 1996. Stabilisation of sialic acids in N-linked
oligosaccharides and gangliosides for analysis by positive ion matrixassisted laser desorption-ionization mass spectrometry. Rapid Commun
Mass Spectrom 10:1027–1032.
Preusser-Kunze A, Mariappan M, Schmidt B, Gande SL, Mutenda K, Wenzel
D, von-Figura K, Dierks T. 2005. Molecular characterization of the
human Ca-formylglycine-generating enzyme. J Biol Chem 280:
14900–14910.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Price NPJ. 2006. Oligosaccharide structures studied by hydrogen-deuterium
exchange and MALDI-TOF mass spectrometry. Anal Chem 78:5302–
5308.
Prior JL, Prior RG, Hitchen PG, Diaper H, Griffin KF, Morris HR, Dell A,
Titball RW. 2003. Characterization of the O antigen gene cluster and
structural analysis of the O antigen of Francisella tularensis subsp.
tularensis. J Med Microbiol 52:845–851.
Psylinakis E, Boneca IG, Mavromatis K, Deli A, Hayhurst E, Foster SJ,
Vårum KM, Bouriotis V. 2005. Peptidoglycan N-acetylglucosamine
deacetylases from Bacillus cereus, highly conserved proteins in
Bacillus anthracis. J Biol Chem 280:30856–30863.
Pudelko M, Lindgren A, Tengel T, Reis CA, Elofsson M, Kihlberg J. 2006.
Formation of lactones from sialylated MUC1 glycopeptides. Org
Biomol Chem 4:713–720.
Raju TS, Scallon BJ. 2006. Glycosylation in the Fc domain of IgG increases
resistance to proteolytic cleavage by papain. Biochem Biophys Res
Commun 341:797–803.
Raman R, Raguram S, Venkataraman G, Paulson JC, Sasisekharan R. 2005.
Glycomics: An integrated systems approach to structure-function
relationships of glycans. Nat Methods 2:817–824.
Raman R, Venkataraman M, Ramakrishnan S, Lang W, Raguram S,
Sasisekharan R. 2006. Advancing glycomics: Implementation strategies at the Consortium for Functional Glycomics. Glycobiology
16:82R–90R.
Rättö M, Verhoef R, Suihko M-L, Blanco A, Schols HA, Voragen AGJ,
Wilting R, Siika-aho M, Buchert J. 2006. Colanic acid is an
exopolysaccharide common to many enterobacteria isolated from
paper-machine slimes. J Ind Microbiol Biotechnol 33:359–367.
Ray B. 2006. Polysaccharides from Enteromorpha compressa: Isolation,
purification and structural features. Carbohydr Polym 66:408–
416.
Rebber BL, Halfacre JA, Beran KA, Beller NR, Gomez M, Bashir S,
Giannakopulos AE, Derrick PJ. 2006. Theoretical investigation of the
proton affinity and gas-phase basicity of neutral x,y-dihydroxybenzoic
acid and its derivatives. Eur J Mass Spectrom 12:385–396.
Regué M, Izquierdo L, Fresno S, Jimenez N, Piqué N, Corsaro MM, Parrilli
M, Naldi T, Merino S, Tomás JM. 2005a. The incorporation of
glucosamine into enterobacterial core lipopolysaccharide. Two enzymatic steps are required. J Biol Chem 280:36648–36656.
Regué M, Izquierdo L, Fresno S, Piqué N, Corsaro MM, Naldi T, De Castro C,
Waidelich D, Merino S, Tomás JM. 2005b. A second outer-core region
in Klebsiella pneumoniae lipopolysaccharide. J Bacteriol 187:4198–
4206.
Reife RA, Coats SR, Al-Qutub M, Dixon DM, Braham PA, Billharz RJ,
Howald WN, Darveau RP. 2006. Porphyromonas gingivalis lipopolysaccharide lipid A heterogeneity: Differential activities of tetraand penta-acylated lipid A structures on E-selectin expression and
TLR4 recognition. Cell Microbiol 8:857–868.
Rele SM, Cui W, Wang L, Hou S, Barr-Zarse G, Tatton D, Gnanou Y, Esko JD,
Chaikof EL. 2005. Dendrimer-like PEO glycopolymers exhibit antiinflammatory properties. J Am Chem Soc 127:10132–10133.
Ren S-F, Zhang L, Cheng Z-H, Guo YL. 2005. Immobilized carbon nanotubes
as matrix for MALDI-TOF-MS analysis: Applications to neutral small
carbohydrates. J Am Soc Mass Spectrom 16:333–339.
Rendic D, Linder A, Paschinger K, Borth N, Wilson IB, Fabini G. 2006.
Modulation of neural carbohydrate epitope expression in Drosophila
melanogaster cells. J Biol Chem 281:3343–3353.
Restelli V, Wang MD, Huzel N, Ethier M, Perreault H, Butler M. 2006. The
effect of dissolved oxygen on the production and the glycosylation
profile of recombinant human erythropoietin produced from CHO cells.
Biotechnol Bioeng 94:481–489.
Reyes E, Córdova A. 2005. Amino acid-catalyzed dynamic kinetic
asymmetric transformations (DYKAT): One-step de novo synthesis of
Mass Spectrometry Reviews DOI 10.1002/mas
&
polyketide sugars from racemic b-hydroxy aldehydes. Tetrahedron Lett
46:6605–6609.
Reynolds CM, Kalb SR, Cotter RJ, Raetz CRH. 2005. A phosphoethanolamine transferase specific for the outer 3-deoxy-D-manno-octulosonic
acid residue of Escherichia coli lipopolysaccharide. Identification of the
eptB gene and Ca2þ hypersensitivity of an eptB deletion mutant. J Biol
Chem 280:21202–21211.
Reynolds CM, Ribeiro AA, McGrath SC, Cotter RJ, Raetz CRH, Trent MS.
2006. An outer membrane enzyme encoded by Salmonella typhimurium
lpxR that removes the 3’-acyloxyacyl moiety of lipid A. J Biol Chem
281:21974–21987.
Ribeiro AO, Tomé JPC, Neves MGPMS, Tomé AC, Cavaleiro JAS, Iamamoto
Y, Torres T. 2006. [1,2,3,4-Tetrakis(a/b-D-galactopyranos-6-yl)phthalocyaninato]zinc(II): Awater-soluble phthalocyanine. Tetrahedron Lett
47:9177–9180.
Robinson S, Routledge A, Thomas-Oates J. 2005. Characterisation and
proposed origin of mass spectrometric ions observed 30 Th above the
ionised molecules of per-O-methylated carbohydrates. Rapid Commun
Mass Spectrom 19:3681–3688.
Röhrig CH, Retz OA, Hareng L, Hartung T, Schmidt RR. 2005. A new
strategy for the synthesis of dinucleotides loaded with glycosylated
amino acids—Investigations on in vitro non-natural amino acid
mutagenesis for glycoprotein synthesis. ChemBioChem 6:1805–1816.
Roper JR, Guther ML, Macrae JI, Prescott AR, Hallyburton I, Acosta-Serrano
A, Ferguson MA. 2005. The suppression of galactose metabolism in
procylic form Trypanosoma brucei causes cessation of cell growth and
alters procyclin glycoprotein structure and copy number. J Biol Chem
280:19728–19736.
Rösch A, Kunz H. 2006. Highly regioselective synthesis of a 3-O-sulfonated
arabino Lewis asparagine building block suitable for glycopeptide
synthesis. Carbohydr Res 341:1597–1608.
Rose NL, Completo GC, Lin S-J, McNeil M, Palcic MM, Lowary TL. 2006.
Expression, purification, and characterization of a galactofuranosyltransferase involved in Mycobacterium tuberculosis arabinogalactan
biosynthesis. J Am Chem Soc 128:6721–6729.
Rousseau C, Ortega-Caballero F, Nordstrøm LU, Christensen B, Petersen TE,
Bols M. 2005. Artificial glycosyl phosphorylases. Chem Eur J 11:
5094–5101.
Roychowdhury A, Wolfert MA, Boons G-J. 2005. Synthesis and proinflammatory properties of muramyl tripeptides containing lysine and
diaminopimelic acid moieties. ChemBioChem 6:2088–2097.
Rustam T, McClean S, Newcombe J, McFadden J, Eales-Reynolds L-J. 2006.
Reduced toxicity of lipo-oligosaccharide from a phoP mutant of
Neisseria meningitidis: An in vitro demonstration. J Endotox Res
12:39–46.
Sagi D, Kienz P, Denecke J, Marquardt T, Peter-Katalinic J. 2005.
Glycoproteomics of N-glycosylation by in-gel deglycosylation and
matrix-assisted laser desorption/ionisation-time of flight mass spectrometry mapping: Application to congenital disorders of glycosylation. Proteomics 5:2689–2701.
Saito R, Yamaguchi K. 2005. Effect of guest compounds on template
polymerization of multivinyl monomer of cyclodextrins. Macromolecules 38:2085–2092.
Saksena R, Adamo R, Kovác P. 2005. Studies toward a conjugate vaccine for
anthrax. Synthesis and characterization of anthrose [4,6-dideoxy-4-(3hydroxy-3-methylbutanamido)-2-O-methyl-D-glucopyranose] and its
methyl glycosides. Carbohydr Res 340:1591–1600.
Saksena R, Zhang J, Kovác P. 2005. Immunogens from a synthetic
hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype
Ogawa. Tetrahedron Asym 16:187–197.
Sandler JS, Forsburg SL, Faulkner DJ. 2005. Bioactive steroidal glycosides
from the marine sponge Erylus lendenfeldi. Tetrahedron 61:1199–
1206.
93
&
HARVEY
Sanz ML, Côté GL, Gibson GR, Rastall RA. 2005. Prebiotic properties of
alternansucrase maltose-acceptor oligosaccharides. J Agric Food Chem
53:5911–5916.
Sanz ML, Côté GL, Gibson GR, Rastall RA. 2006. Selective fermentation of
gentiobiose-derived oligosaccharides by human gut bacteria and
influence of molecular weight. FEMS Microbiol Ecol 56:383–388.
Sanz-Nebot V, Benavente F, Giménez E, Barbosa J. 2005. Capillary
electrophoresis and matrix-assisted laser desorption/ionization-time
of flight-mass spectrometry for analysis of the novel erythropoiesisstimulating protein (NESP). Electrophoresis 26:1451–1456.
Sarkar M, Leventis PA, Silvescu CI, Reinhold VN, Schachter H, Boulianne
GL. 2006. Null mutations in drosophila N-acetylglucosaminyltransferase I produce defects in locomotion and a reduced life span. J Biol Chem
281:12776–12785.
Sasaki A, Ishimizu T, Geyer R, Hase S. 2005. Synthesis of b-mannosides
using the transglycosylation activity of endo-b-mannosidase from
Lilium longiflorum. FEBS J 272:1660–1668.
Sasaki S, Shirahashi Y, Nishiyama K, Watanabe H, Hayase F. 2006.
Identification of a novel blue pigment as a melanoidin intermediate in
the D-xylose-glycine reaction system. Biosci Biotechnol Biochem
70:2529–2531.
Sasisekharan R, Shriver Z, Sundaram M, Venkataraman G. 2006. Analytical
techniques for the characterization and sequencing of glycosylaminoglycans. In: Wong C-H, editor. Carbohydrate-based drug discovery.
Hoboken, NJ: Wiley VCH. pp 517–540.
Sato H, Seino T, Yamamoto A, Torimura M, Tao H. 2005. Soft laser
desorption/ionization mass spectrometry using a pyroelectric ceramic
plate. Chem Lett 34:1178–1179.
Sato K, Hada N, Takeda T. 2006. Syntheses of new peptidic glycoclusters
derived from b-alanine: Di- and trimerized glycoclusters and
glycocluster-clusters. Carbohydr Res 341:836–845.
Satterfield MB, Welch MJ. 2005. Comparison by LC-MS and MALDI-MS of
prostate-specific antigen from five commercial sources with certified
reference material 613. Clin Biochem 38:166–174.
Schagerlöf H, Richardson S, Momcilovic D, Brinkmalm G, Wittgren B,
Tjerneld F. 2006. Characterization of chemical substitution of
hydroxypropyl cellulose using enzymatic degradation. Biomacromolecules 7:80–85.
Schimmel J, Eleutério MIP, Ritter G, Schmidt RR. 2006. Synthesis of
saponins with cholestanol, cholesterol, and friedelanol as aglycones.
Eur J Org Chem:1701–1721.
Schmitt A, Bigl K, Meiners I, Schmitt J. 2006. Induction of reactive oxygen
species and cell survival in the presence of advanced glycation end
products and similar structures. Biochim Biophys Acta 1763:927–936.
Schmitt A, Gasic-Milenkovic J, Schmitt J. 2005. Characterization of
advanced glycation end products: Mass changes in correlation to side
chain modifications. Anal Biochem 346:101–106.
Schulz E, Karas M, Rosu F, Gabelica V. 2006. Influence of the matrix on
analyte fragmentation in atmospheric pressure MALDI. J Am Soc Mass
Spectrom 17:1005–1013.
Schuster M, Umana P, Ferrara C, Brünker P, Gerdes C, Waxenecker G,
Wiederkum S, Schwager C, Loibner H, Himmler G, Mudde GC. 2005.
Improved effector functions of a therapeutic monoclonal Lewis Yspecific antibody by glycoform engineering. Cancer Res 65:7934–
7941.
Schweizer F, Hindsgaul O. 2006. Synthesis of a galacto-configured Cketoside-based g-sugar-amino acid and its use in peptide coupling
reactions. Carbohydr Res 341:1730–1736.
Šebela M, Štosová T, Havli J, Wielsch N, Thomas H, Zdráhal Z, Shevchenko
A. 2006. Thermostable trypsin conjugates for high-throughput
proteomics: Synthesis and performance evaluation. Proteomics 6:
2959–2963.
Sekiya S, Wada Y, Tanaka K. 2005. Derivatization for stabilizing sialic acids
in MALDI-MS. Anal Chem 77:4962–4968.
94
Sekiya S, Yamaguchi Y, Kato K, Tanaka K. 2005. Mechanistic elucidation of
the formation of reduced 2-aminopyridine-derivatized oligosaccharides
and their application in matrix-assisted laser desorption/ionization mass
spectrometry. Rapid Commun Mass Spectrom 19:3607–3611.
Seo E-S, Lee J-H, Park J-Y, Kim D, Han H-J, Robyt JF. 2005. Enzymatic
synthesis and anti-coagulant effect of salicin analogs by using the
Leuconostoc mesenteroides glucansucrase acceptor reaction. J Biotechnol 117:31–38.
Seppala U, Hagglund P, Wurtzen PA, Ipsen H, Thorsted P, Lenhard T,
Roepstorff P, Spangfort MD. 2005. Molecular characterization of major
cat allergen Fel d 1: Expression of heterodimer by use of a baculovirus
expression system. J Biol Chem 280:3208–3216.
Seyfried NT, Blundell CD, Day AJ, Almond A. 2005. Preparation and
application of biologically active fluorescent hyaluronan oligosaccharides. Glycobiology 15:303–312.
Shao N, Guo Z. 2005. Solution-phase synthesis with solid-state workup of an
O-glycopeptide with a cluster of cancer-related T antigens. Org Lett
7:3589–3592.
Sherlock O, Dobrindt U, Jensen JP, Vejborg RM, Klemm P. 2006.
Glycosylation of the self-recognizing Escherichia coli Ag43 autotransporter protein. J Bacteriol 188:1798–1807.
Shimizu M, Igasaki T, Yamada M, Yuasa K, Hasegawa J, Kato T, Tsukagoshi
H, Nakamura K, Fukuda H, Matsuoka K. 2005. Experimental
determination of proline hydroxylation and hydroxyproline arabinogalactosylation motifs in secretory proteins. Plant J 42:877–889.
Shimma Y-I, Saito F, Oosawa F, Jigami Y. 2006. Construction of a library of
human glycosyltransferases immobilized in the cell wall of Saccharomyces cerevisiae. Appl Environ Microbiol 72:7003–7012.
Shinya T, Ménard R, Kozone I, Matsuoka H, Shibuya N, Kauffmann S,
Matsuoka K, Saito M. 2006. Novel b-1,3-, 1,6-oligoglucan elicitor from
Alternaria alternata 102 for defense responses in tobacco. FEBS J
273:2421–2431.
Shoda S-I, Misawa Y, Nishijima Y, Tawata Y, Kotake T, Noguchi M,
Kobayashi A, Watanabe T. 2006. Chemo-enzymatic synthesis of novel
oligo-N-acetyllactosamine derivatives having a b(1-4)-b(1-6) repeating
unit by using transition state analogue substrate. Cellulose 13:477–484.
Sicherl F, Wittmann V. 2005. Orthogonally protected sugar diamino acids as
building blocks for linear and branched oligosaccharide mimetics.
Angew Chem Int Ed Engl 44:2096–2099.
Siemiatkoski J, Lyubarskaya Y, Houde D, Tep S, Mhatre R. 2006. A
comparison of three techniques for quantitative carbohydrate analysis
used in characterization of therapeutic antibodies. Carbohydr Res
341:410–419.
Silchenko AS, Avilov SA, Antonov AS, Kalinovsky AI, Dmitrenok PS,
Kalinin VI, Stonik VA, Woodward C, Collin PD. 2005. Glycosides from
the sea cucumber Cucumaria frondosa. III. Structure of frondosides A21, A2-2, A2-3, and A2-6, four new minor monosulfated triterpene
glycosides. Can J Chem 83:21–27.
Silipo A, Lanzetta R, Parrilli M, Sturiale L, Garozzo D, Nazarenko EL,
Gorshkova RP, Ivanova EP, Molinaro A. 2005a. The complete structure
of the core carbohydrate backbone from the LPS of marine halophilic
bacterium Pseudoalteromonas carrageenovora type strain IAM
12662T. Carbohydr Res 340:1475–1482.
Silipo A, Leone S, Molinaro A, Sturiale L, Garozzo D, Nazarenko EL,
Gorshkova RP, Ivanova EP, Lanzetta R, Parrilli M. 2005b. Complete
structural elucidation of a novel lipooligosaccharide from the outer
membrane of the marine bacterium Shewanella pacifica. Eur J Org
Chem:2281–2291.
Silipo A, Molinaro A, Cescutti P, Bedini E, Rizzo R, Parrilli M, Lanzetta R.
2005c. Complete structural characterization of the lipid A fraction of a
clinical strain of B. cepacia genomovar I lipopolysaccharide.
Glycobiology 15:561–570.
Silipo A, Molinaro A, Comegna D, Struiale L, Cescutti P, Garozzo D,
Lanzetta R, Parrilli M. 2006. Full structural characterisation of the
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
lipooligosaccharide of a Burkholderia pyrrocinia clinical isolate. Eur J
Org Chem:4874–4883.
Silipo A, Molinaro A, Nazarenko EL, Sturiale L, Garozzo D, Gorshkova RP,
Nedashkovskaya OI, Lanzetta R, Parrilli M. 2005d. Structural
characterization of the carbohydrate backbone of the lipooligosaccharide of the marine bacterium Arenibacter certesii strain KMM 3941T.
Carbohydr Res 340:2540–2549.
Silipo A, Molinaro A, Sturiale L, Dow JM, Erbs G, Lanzetta R, Newman MA, Parrilli M. 2005e. The elicitation of plant innate immunity by
lipooligosaccharide of Xanthomonas campestris. J Biol Chem 280:
33660–33668.
Silván JM, van de Lagemaat J, Olano A, del Castillo MD. 2006. Analysis and
biological properties of amino acid derivates formed by Maillard
reaction in foods. J Pharm Biomed Anal 41:1543–1551.
Skhirtladze A, Plaza A, Montoro P, Benidze M, Kemertelidze E, Pizza C,
Piacente S. 2006. Furostanol saponins from Yucca gloriosa L. rhizomes.
Biochem Syst Ecol 34:809–814.
Skov LK, Seppala U, Coen JJ, Crickmore N, King TP, Monsalve R, Kastrup
JS, Spangfort MD, Gajhede M. 2006. Structure of recombinant Ves v 2
at 2.0 Angstrom resolution: Structural analysis of an allergenic
hyaluronidase from wasp venom. Acta Cryst 62:595–604.
Smith DK, Hirst AR, Love CS, Hardy JG, Brignell SV, Huang B. 2005. Selfassembly using dendritic building blocks—Towards controllable
nanomaterials. Prog Polym Sci 30:220–293.
Snovida SI, Chen VC, Krokhin O, Perreault H. 2006. Isolation and
identification of sialylated glycopeptides from bovine a1-acid glycoprotein by off-line capillary electrophoresis MALDI-TOF mass
spectrometry. Anal Chem 78:6556–6563.
Snovida SI, Chen VC, Perreault H. 2006. Use of a 2,5-dihydroxybenzoic
acid/aniline MALDI matrix for improved detection and on-target
derivatization of glycans: A preliminary report. Anal Chem 78:8561–
8568.
Sol A, Charmot A, Krausz P, Trombotto S, Queneau Y. 2005. Synthesis of new
glucosylated porphyrins bearing an a-D-linkage. J Carbohydr Chem
25:345–360.
Sol V, Chaleix V, Champavier Y, Granet R, Huang Y-M, Krausz P. 2006.
Glycosyl bis-porphyrin conjugates: Synthesis and potential application
in PDT. Bioorg Med Chem 14:7745–7760.
Soltés L, Stankovskyá M, Brezová V, Schiller J, Arnhold J, Mendichi R,
Kogan G, Gemeiner P. 2006. Hyaluronan degradation by copper(II)
chloride and ascorbate: Rotational viscometric, EPR spin-trapping and
MALDI-TOF mass spectrometric investigations. Carbohydr Res
341:2826–2834.
Sørensen AL, Reis CA, Tarp MA, Mandel U, Ramachandran K, Sankaranarayanan V, Schwientek T, Graham R, Taylor-Papadimitriou J, Hollingsworth MA, Burchell J, Clausen H. 2006. Chemoenzymatically
synthesized multimeric Tn/STn MUC1 glycopeptides elicit cancerspecific anti-MUC1 antibody responses and override tolerance.
Glycobiology 16:96–107.
Soria-Dı́az ME, Rodrı́guez-Carvajal MA, Tejero-Mateo P, Espartero JL,
Morón B, Sousa C, Megı́as M, Thomas-Oates J, Gil-Serrano AM. 2006.
Structural determination of the Nod factors produced by Rhizobium
gallicum bv. gallicum R602. FEMS Microbiol Lett 255:164–173.
Sparbier K, Koch S, Kessler I, Wenzel T, Kostrzewa M. 2005. Selective
isolation of glycoproteins and glycopeptides for MALDI-TOF MS
detection supported by magnetic particles. J Biomol Tech 16:405–411.
Sparbier K, Wenzel T, Kostrzewa M. 2006. Exploring the binding profiles of
ConA, boronic acid and WGA by MALDI-TOF/TOF MS and magnetic
particles. J Chromatogr B 840:29–36.
Srinivas O, Mitra N, Surolia A, Jayaraman N. 2005. Photoswitchable cluster
glycosides as tools to probe carbohydrate-protein interactions: Synthesis and lectin-binding studies of azobenzene containing multivalent
sugar ligands. Glycobiology 15:861–873.
Mass Spectrometry Reviews DOI 10.1002/mas
&
St. John FJ, Rice JD, Preston JF. 2006. Characterization of XynC from
Bacillus subtilis subsp. subtilis strain 168 and analysis of its role in
depolymerization of glucuronoxylan. J Bacteriol 188:8617–8626.
Stadthagen G, Jackson M, Charles P, Boudou F, Barilone N, Huerre M,
Constant P, Liav A, Bottova I, Nigou J, Brando T, Puzo G, Daffé M,
Benjamin P, Coade S, Buxton RS, Tascon RE, Rae A, Robertson BD,
Lowrie DB, Young DB, Gicquel B, Griffin R. 2006. Comparative
investigation of the pathogenicity of three Mycobacterium tuberculosis
mutants defective in the synthesis of p-hydroxybenzoic acid derivatives.
Microbes Infect 8:2245–2253.
Stadthagen G, Kordulakova J, Griffin R, Constant P, Bottova I, Barilone N,
Gicquel B, Daffe M, Jackson M. 2005. p-Hydroxybenzoic acid
synthesis in Mycobacterium tuberculosis. J Biol Chem 280:40699–
40706.
Staehelin C, Forsberg LS, D’Haeze W, Gao M-Y, Carlson RW, Xie Z-P,
Pellock BJ, Jones KM, Walker GC, Streit WR, Broughton WJ. 2006.
Exo-oligosaccharides of Rhizobium sp. strain NGR234 are required for
symbiosis with various legumes. J Bacteriol 188:6168–6178.
Staniszewska M, Jarosz S, Jon M, Gamian A. 2005. Advanced glycation endproducts prepared in solution under high pressure contain epitopes
distinct from those formed in the dry reaction at high temperature. Arch
Immunol Exp Ther 53:71–78.
Stanley P, Sundaram S, Tang J, Shi S. 2005. Molecular analysis of three gainof-function CHO mutants that add the bisecting GlcNAc to N-glycans.
Glycobiology 15:43–53.
Stead C, Tran A, Ferguson DJ, McGrath S, Cotter R, Trent S. 2005. A novel 3deoxy-D-manno-octulosonic acid (Kdo) hydrolase that removes the
outer Kdo sugar of Helicobacter pylori lipopolysaccharide. J Bacteriol
187:3374–3383.
Steiner K, Pohlentz G, Dreisewerd K, Berkenkamp S, Messner P, PeterKatalinic J, Schäffer C. 2006. New Insights into the glycosylation of the
surface layer protein SgsE from Geobacillus stearothermophilus NRS
2004/3a. J Bacteriol 188:7914–7921.
Strasser R, Schoberer J, Jin C, Glössl J, Mach L, Steinkellner H. 2006.
Molecular cloning and characterization of Arabidopsis thaliana Golgi
a-mannosidase II, a key enzyme in the formation of complex N-glycans
in plants. Plant J 45:789–803.
Strasser R, Stadlmann J, Svoboda B, Altmann F, Glössl J, Mach L. 2005.
Molecular basis of N-acetylglucosaminyltransferase I deficiency in
Arabidopsis thaliana plants lacking complex N-glycans. Biochem J
387:385–391.
Stübiger G, Marchetti M, Nagano M, Grimm R, Gmeiner G, Reichel C,
Allmaier G. 2005a. Characterization of N- and O-glycopeptides of
recombinant human erythropoietins as potential biomarkers for doping
analysis by means of microscale sample purification combined with
MALDI-TOF and quadrupole IT/RTOF mass spectrometry. J Sep Sci
28:1764–1778.
Stübiger G, Marchetti M, Nagano M, Reichel C, Gmeiner G, Allmaier G.
2005b. Characterisation of intact recombinant human erythropoietins
applied in doping by means of planar gel electrophoretic techniques and
matrix-assisted laser desorption/ionisation linear time-of-flight mass
spectrometry. Rapid Commun Mass Spectrom 19:728–742.
Sturiale L, Barone R, Fiumara A, Perez M, Zaffanello M, Sorge G, Pavone L,
Tortorelli S, O’Brien JF, Jaeken J, Garozzo D. 2005a. Hypoglycosylation with increased fucosylation and branching of serum transferrin Nglycans in untreated galactosemia. Glycobiology 15:1268–1276.
Sturiale L, Garozzo D, Silipo A, Lanzetta R, Parrilli M, Molinaro A. 2005b.
New conditions for matrix-assisted laser desorption/ionization mass
spectrometry of native bacterial R-type lipopolysaccharides. Rapid
Commun Mass Spectrom 19:1829–1834.
Subramaniam V, Gurcha SS, Besra GS, Lowary TL. 2005. Modified mannose
disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent a-(1-6)-mannosyltransferase involved in
95
&
HARVEY
mycobacterial lipoarabinomannan biosynthesis. Bioorg Med Chem
13:1083–1094.
Sun Y, Hayakawa S, Ogawa M, Izumori K. 2005. Evaluation of the site
specific protein glycation and antioxidant capacity of rare sugarprotein/peptide conjugates. J Agric Food Chem 53:10205–10212.
Sun Y, Hayakawa S, Puangmanee S, Izumori K. 2006. Chemical properties
and antioxidative activity of glycated a-lactalbumin with a rare sugar, Dallose, by Maillard reaction. Food Chem 95:509–517.
Sundgren A, Lahmann M, Oscarson S. 2005. Block synthesis of
Streptococcus pneumoniae type 14 capsular polysaccharide structures.
J Carbohydr Chem 24:379–391.
Suzuki H, Yamagaki T, Tachibana K. 2005. Optimization of matrix and
amount of ammonium chloride additive for effective ionization of
neutral oligosaccharides as chloride ion adducts in negative-mode
MALDI-TOF mass spectrometry. J Mass Spectrom Soc Jpn 53:227–
229.
Suzuki H, Yamagaki T, Tachibana K. 2006. Optimization for effective
ionization of neutral oligosaccharides in negative-ion MALDI-MS.
Nippon Kagakkai Koen Yokoshu 86:503.
Suzuki S, Fujimori T, Yodoshi M. 2006. Recovery of free oligosaccharides
from derivatives labeled by reductive amination. Anal Biochem 354:
94–103.
Suzuki T, Hara I, Nakano M, Shigeta M, Nakagawa T, Kondo A, Funakoshi Y,
Taniguchi N. 2006a. Man2C1, an a-mannosidase, is involved in
the trimming of free oligosaccharides in the cytosol. Biochem J 400:
33–41.
Suzuki T, Hara I, Nakano M, Zhao G, Lennarz WJ, Schindelin H, Taniguchi
N, Totani K, Matsuo I, Ito Y. 2006b. Site-specific labeling of
cytoplasmic peptide: N-glycanase by N,N’-diacetylchitobiose-related
compounds. J Biol Chem 281:22152–22160.
Suzuki Y, Suzuki M, Ito E, Goto-Inoue N, Miseki K, Iida J, Yamazaki Y,
Yamada M, Suzuki A. 2006c. Convenient structural analysis of
glycosphingolipids using MALDI-QIT-TOF mass spectrometry with
increased laser power and cooling gas flow. J Biochem (Tokyo) 139:
771–777.
Suzuki Y, Suzuki M, Ito E, Ishii H, Miseki K, Suzuki A. 2005. Convenient and
rapid analysis of linkage isomers of fucose-containing oligosaccharides
by matrix-assisted laser desorption/ionization quadrupole ion trap timeof-flight mass spectrometry. Glycoconj J 22:427–431.
Suzuki Y, Suzuki M, Nakahara Y, Ito Y, Ito E, Goto N, Miseki K, Iida J, Suzuki
A. 2006d. Structural characterization of glycopeptides by N-terminal
protein ladder sequencing. Anal Chem 78:2239–2243.
Svarovsky SA, Szekely Z, Barchi JJ. 2005. Synthesis of gold nanoparticles
bearing the Thomsen-Friedenreich disaccharide: A new multivalent
presentation of an important tumor antigen. Tetrahedron Asym 16:587–
598.
Swanson KV, Griffiss JM. 2006. Separation and identification of neisserial
lipooligosaccharide oligosaccharides using high-performance anionexchange chromatography with pulsed amperometric detection.
Carbohydr Res 341:388–396.
Swanwick RS, Daines AM, Flitsch SL, Allemann RK. 2005. Synthesis of
homogenous site-selectively glycosylated proteins. Org Biomol Chem
3:572–574.
Szafranek J, Kumirska J, Czerwicka M, Kunikowska D, Dziadziuszko H,
Glosnicka R. 2006. Structure and heterogeneity of the O-antigen chain
of Salmonella agona lipopolysaccharide. FEMS Immunol Med Microbiol 48:223–236.
Szolcsányi P, Gracza T. 2006. PdCl2/CuCl2-catalysed chlorocyclisation of
sugar-derived aminoalkenitols in the synthesis of new iminohexitols.
Tetrahedron 62:8498–8502.
Sztaricskai F, Sum A, Roth E, Pelyvás IF, Sándor S, Batta G, Herczegh P,
Reményi J, Miklán Z, Hudecz F. 2005. A new class of semisynthetic
anthracycline glycoside antibiotics incorporating a squaric acid moiety.
J Antibiot 58:704–714.
96
Taguchi F, Takeuchi K, Katoh E, Murata K, Suzuki T, Marutani M, Kawasaki
T, Eguchi M, Katoh S, Kaku H, Yasuda C, Inagaki Y, Toyoda K,
Shiraishi T, Ichinose Y. 2006. Identification of glycosylation genes and
glycosylated amino acids of flagellin in Pseudomonas syringae pv.
tabaci. Cell Microbiol 8:923–938.
Taira H, Nagase H, Endo T, Ueda H. 2006. Isolation, purification and
characterization of large-ring cyclodextrins (CD36-CD39). J Incl
Phenom Macrocyclic Chem 56:23–28.
Tajiri M, Yoshida S, Wada Y. 2005. Differential analysis of site-specific
glycans on plasma and cellular fibronectins: Application of a hydrophilic affinity method for glycopeptide enrichment. Glycobiology
15:1332–1340.
Takahashi H, Takashima Y, Yamaguchi H, Harada A. 2006. Selection between
pinching-type and supramolecular polymer-type complexes by acyclodextrin-b-cyclodextrin hetero-dimer and hetero-cinnamamide
guest dimers. J Org Chem 71:4878–4883.
Takahashi N, Okada H, Fukushi E, Onodera S, Nishimoto T, Kawabata J,
Shiomi N. 2005. Structural analysis of six novel oligosaccharides
synthesized by glucosyl transfer from b-D-glucose 1-phosphate to
raffinose and stachyose using Thermoanaerobacter brockii kojibiose
phosphorylase. Tetrahedron Asym 16:57–63.
Takashiba M, Chiba Y, Jigami Y. 2006. Identification of phosphorylation sites
in N-linked glycans by matrix-assisted laser desorption/ionization timeof-flight mass spectrometry. Anal Chem 78:5208–5213.
Takeda M, Makita H, Ohno K, Nakahara Y, Koizumi J. 2005. Structural
analysis of the sheath of a sheathed bacterium, Leptothrix cholodnii. Int
J Biol Macromol 37:92–98.
Takemori N, Komori N, Matsumoto H. 2006. Highly sensitive multistage
mass spectrometry enables small-scale analysis of protein glycosylation
from two-dimensional polyacrylamide gels. Electrophoresis 27:1394–
1406.
Talabnin K, Yagi H, Takahashi N, Suzuki T, Kato K, Uemura H, Saichua P,
Kaewkes S, Wongkham S, Suzuki Y, Sripa B. 2006. Glycobiological
study of adult Opisthorchis viverrini: Characterization of N-linked
oligosaccharides. Mol Biochem Parasitol 147:230–233.
Tamayo R, Choudhury B, Septer A, Merighi M, Carlson R, Gunn JS. 2005.
Identification of cptA, a PmrA-regulated locus required for phosphoethanolamine modification of the Salmonella enterica serovar typhimurium lipopolysaccharide core. J Bacteriol 187:3391–3399.
Tanabe K, Ikenaka K. 2006. In-column removal of hydrazine and Nacetylation of oligosaccharides released by hydrazionolysis. Anal
Biochem 348:324–326.
Tanaka E, Nakahara Y, Kuroda Y, Takano Y, Kojima N, Hojo H, Nakahara Y.
2006. Chemoenzymatic synthesis of a MUC1 glycopeptide carrying
non-natural sialyl TF-b O-glycan. Biosci Biotechnol Biochem 70:
2515–2522.
Tang H, Mechref Y, Novotny MV. 2005. Automated interpretation of MS/MS
spectra of oligosaccharides. Bioinformatics 21:i431–i439.
Tang S-Y, Yang S-J, Cha H, Woo E-J, Park C, Park K-H. 2006. Contribution of
W229 to the transglycosylation activity of 4-a-glucanotransferase from
Pyrococcus furiosus. Biochim Biophys Acta 1764:1633–1638.
Taylor AM, Holst O, Thomas-Oates J. 2006. Mass spectrometric profiling of
O-linked glycans released directly from glycoproteins in gels using ingel reductive b-elimination. Proteomics 6:2936–2946.
ten Cate MGJ, Omerovi M, Oshovsky GV, Crego-Calama M, Reinhoudt DN.
2005. Self-assembly and stability of double rosette nanostructures with
biological functionalities. Org Biomol Chem 3:3727–3733.
Terada M, Khoo KH, Inoue R, Chen CI, Yamada K, Sakaguchi H, Kadowaki
N, Ma BY, Oka S, Kawasaki T, Kawasaki N. 2005. Characterization of
oligosaccharide ligands expressed on SW1116 cells recognized by
mannan-binding protein. A highly fucosylated polylactosamine type Nglycan. J Biol Chem 280:10897–10913.
Teramoto N, Abe Y, Enomoto A, Watanabe D, Shibata M. 2005. Novel
synthetic route of a trehalose-based linear polymer by ring opening of
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
two epoxy groups with aliphatic diamine. Carbohydr Polym 59:217–
224.
Terinek M, Vasella A. 2005. Synthesis and evaluation of two mannosaminederived lactone-type inhibitors of snail b-mannosidase. Tetrahedron
Asym 16:449–469.
Thaysen-Andersen M, Højrup P. 2006. Enrichment and characterization of
glycopeptides from gel-separated glycoproteins. Am Biotechnol Lab
24:14–17.
Tholey A, Heinzle E. 2006. Ionic (liquid) matrices for matrix-assisted laser
desorption/ionization mass spectrometry-applications and perspectives. Anal Bioanal Chem 386:24–37.
Thoma G, Streiff MB, Katopodis AG, Duthaler RO, Voelcker NH, Ehrhardt C,
Masson C. 2006. Non-covalent polyvalent ligands by self-assembly of
small glycodendrimers: A novel concept for the inhibition of polyvalent
carbohydrate-protein interactions in vitro and in vivo. Chem Eur J
12:99–117.
Tie J-K, Zheng M-Y, Pope RM, Straight DL, Stafford DW. 2006.
Identification of the N-linked glycosylation sites of vitamin Kdependent carboxylase and effect of glycosylation on carboxylase
function. Biochemistry 45:14755–14763.
Tolbert TJ, Franke D, Wong C-H. 2005. A new strategy for glycoprotein
synthesis: Ligation of synthetic glycopeptides with truncated proteins
expressed in E. coli as TEV protease cleavable fusion protein. Bioorg
Med Chem 13:909–915.
Totani K, Ihara Y, Matsuo I, Koshino H, Ito Y. 2005. Synthetic substrates for
an endoplasmic reticulum protein-folding sensor, UDP-glucose:
Glycoprotein glucosyltransferase. Angew Chem Int Ed Engl 44:
7950–7954.
Totani K, Matsuo I, Ihara Y, Ito Y. 2006. High-mannose-type glycan
modifications of dihydrofolate reductase using glycan-methotrexate
conjugates. Bioorg Med Chem 14:5220–5229.
Touboul D, Roy S, Germain DP, Baillet A, Brion F, Prognon P, Chaminade P,
Laprévote O. 2005. Fast fingerprinting by MALDI-TOF mass
spectrometry of urinary sediment glycosphingolipids in Fabry disease.
Anal Bioanal Chem 382:1209–1216.
Tran AX, Lester ME, Stead CM, Raetz CRH, Maskell DJ, McGrath SC,
Cotter RJ, Trent MS. 2005. Resistance to the antimicrobial peptide
polymyxin requires myristoylation of Escherichia coli and Salmonella
typhimurium lipid A. J Biol Chem 280:28186–28194.
Tran AX, Whittimore JD, Wyrick PB, McGrath SC, Cotter RJ, Trent MS.
2006. The lipid A 1-phosphatase of Helicobacter pylori is required for
resistance to the antimicrobial peptide polymyxin. J Bacteriol 188:
4531–4541.
Tranchepain F, Deschrevel B, Courel M-N, Levasseur N, Le Cerf D,
Loutelier-Bourhis C, Vincent J-C. 2006. A complete set of hyaluronan
fragments obtained from hydrolysis catalyzed by hyaluronidase:
Application to studies of hyaluronan mass distribution by simple HPLC
devices. Anal Biochem 348:232–242.
Triguero A, Cabrera G, Cremata JA, Yuen C-T, Wheeler J, Ramirez NI. 2006.
Plant-derived mouse IgG monoclonal antibody fused to KDEL
endoplasmic reticulum-retention signal is N-glycosylated homogeneously throughout the plant with mostly high-mannose-type N-glycans.
Plant Biotechnol J 3:449–457.
Trimpin S, Räder HJ, Müllen K. 2006. Investigations of theoretical principles
for MALDI-MS derived from solvent-free sample preparation: Part I.
Preorganization. Int J Mass Spectrom 253:13–21.
Tropis M, Meniche X, Wolf A, Gebhardt H, Strelkov S, Chami M, Schomburg
D, Kramer R, Morbach S, Daffe M. 2005. The crucial role of trehalose
and structurally related oligosaccharides in the biosynthesis and transfer
of mycolic acids in Corynebacterineae. J Biol Chem 280:26573–
26585.
Turek D, Sundgren A, Lahmann M, Oscarson S. 2006. Synthesis of
oligosaccharides corresponding to Vibrio cholerae O139 polysacchar-
Mass Spectrometry Reviews DOI 10.1002/mas
&
ide structures containing dideoxy sugars and a cyclic phosphate. Org
Biomol Chem 4:1236–1241.
Ueki M, Yamaguchi M. 2005. Analysis of acidic carbohydrates as their
quaternary ammonium or phosphonium salts by matrix-assisted laser
desorption/ionization mass spectrometry. Carbohydr Res 340:1722–
1731.
Uematsu R, Furukawa J-I, Nakagawa H, Shinohara Y, Deguch K, Monde K,
Nishimura S-I. 2005. High throughput quantitative glycomics and
glycoform-focused proteomics of murine dermis and epidermis. Mol
Cell Proteomics 4:1977–1989.
Uemura Y, Asakuma S, Nakamura T, Arai I, Taki M, Urashima T. 2005.
Occurrence of a unique sialyl tetrasaccharide in colostrum of a
bottlenose dolphin (Tursiops truncatus). Biochim Biophys Acta
1725:290–297.
Ullmer R, Plematl A, Rizzi A. 2006. Derivatization by 6-aminoquinolyl-Nhydroxysuccinimidyl carbamate for enhancing the ionization yield of
small peptides and glycopeptides in matrix-assisted laser desorption/
ionization and electrospray ionization mass spectrometry. Rapid
Commun Mass Spectrom 20:1469–1479.
Usuki S, Thompson SA, Rivner MH, Taguchi K, Shibata K, Ariga T, Yu RK.
2006. Molecular mimicry: Sensitization of Lewis rats with Campylobacter jejuni lipopolysaccharides induces formation of antibody toward
GD3 ganglioside. J Neurosci Res 83:274–284.
Utz S, Roditi I, Renggli CK, Almeida IC, Acosta-Serrano A, Bütikofer P.
2006. Trypanosoma congolense procyclins: Unmasking cryptic major
surface glycoproteins in procyclic forms. Eukaryot Cell 5:1430–1440.
Vaidyanathan G, Affleck DJ, Schottelius M, Wester H, Friedman HS,
Zalutsky MR. 2006. Synthesis and evaluation of glycosylated octreotate
analogues labeled with radioiodine and 211At via a tin precursor.
Bioconjug Chem 17:195–203.
Van Riet E, Wuhrer M, Wahyuni S, Retra K, Deelder AM, Tielens AGM, Van
Der Kleij D, Yazdanbakhsh M. 2006. Antibody responses to Ascarisderived proteins and glycolipids: The role of phosphorylcholine.
Parasite Immunol 28:363–371.
van Roon A-MM, Aguilera B, Cuenca F, van Remoortere A, van der Marel
GA, Deelder AM, Overkleeft HS, Hokke CH. 2005. Synthesis and
antibody-binding studies of a series of parasite fuco-oligosaccharides.
Bioorg Med Chem 13:3553–3564.
Vedam V, Kannenberg E, Datta A, Brown D, Haynes-Gann JG, Sherrier DJ,
Carlson RW. 2006. The pea nodule environment restores the ability of a
Rhizobium leguminosarum lipopolysaccharide acpXL mutant to add
27-hydroxyoctacosanoic acid to its lipid A. J Bacteriol 188:2126–
2133.
Verhagen C, Bryld T, Raunkjær M, Vogel S, Buchalová K, Wengel J. 2006. A
conformationally locked aminomethyl C-glycoside and studies on its Npyren-1-ylcarbonyl derivative inserted into oligodeoxynucleotides. Eur
J Org Chem:2538–2548.
Verhoef R, Beldman G, Schols HA, Siika-aho M, Rättö M, Buchert J, Voragen
AGJ. 2005. Characterisation of a 1,4-b-fucoside hydrolase degrading
colanic acid. Carbohydr Res 340:1780–1788.
Vialle S, Sepulcri P, Dubayle J, Talaga P. 2005. The teichoic acid (Cpolysaccharide) synthesized by Streptococcus pneumoniae serotype 5
has a specific structure. Carbohydr Res 340:91–96.
Vila-Perelló M, Gallego R, Andreu D. 2005. A simple approach to welldefined sugar-coated surfaces for interaction studies. ChemBioChem
6:1831–1838.
Vinogradov E, Caroff M. 2005. Structure of the Bordetella trematum LPS Ochain subunit. FEBS Lett 579:18–24.
von der Lieth C-W, Lütteke T, Frank M. 2006. The role of informatics in
glycobiology research with special emphasis on automatic interpretation of MS spectra. Biochim Biophys Acta 1760:568–577.
von Witzendorff D, Ekhlasi-Hundrieser M, Dostalova Z, Resch M, Rath D,
Michelmann HW, Topfer-Petersen E. 2005. Analysis of N-linked
97
&
HARVEY
glycans of porcine zona pellucida glycoprotein ZPA by MALDI-TOF
MS: A contribution to understanding zona pellucida structure.
Glycobiology 15:475–488.
Vosseller K, Trinidad JC, Chalkley RJ, Specht CG, Thalhammer A, Lynn AJ,
Snedecor JO, Guan S, Medzihradszky KF, Maltby DA, Schoepfer R,
Burlingame AL. 2006. O-linked N-acetylglucosamine proteomics of
postsynaptic density preparations using lectin weak affinity chromatography and mass spectrometry. Mol Cell Proteomics 5:923–934.
Voutquenne L, Guinot P, Froissard C, Thoison O, Litaudon M, Lavaud C.
2005. Haemolytic acylated triterpenoid saponins from Harpullia
austro-caledonica. Phytochemistry 66:825–835.
Wa C, Cerny R, Hage DS. 2006. Obtaining high sequence coverage in matrixassisted laser desorption time-of-flight mass spectrometry for studies of
protein modification: Analysis of human serum albumin as a model.
Anal Biochem 349:229–241.
Wacker M, Feldman MF, Callewaert N, Kowarik M, Clarke BR, Pohl NL,
Hernandez M, Vines ED, Valvano MA, Whitfield C, Aebi M. 2006.
Substrate specificity of bacterial oligosaccharyltransferase suggests a
common transfer mechanism for the bacterial and eukaryotic systems.
Proc Natl Acad Sci USA 103:7088–7093.
Wacker R, Stoeva S, Betzel C, Voelter W. 2005. Complete structure
determination of N-acetyl-D-galactosamine-binding mistletoe lectin-3
from Viscum album L. album. J Peptide Sci 11:289–302.
Wada Y. 2006. Mass spectrometry for congenital disorders of glycosylation,
CDG. J Chromatogr B 838:3–8.
Wahrenbrock MG, Varki A. 2006. Multiple hepatic receptors cooperate to
eliminate secretory mucins aberrantly entering the bloodstream: Are
circulating cancer mucins the ‘‘tip of the iceberg’’? Cancer Res
66:2433–2441.
Walter M, Wiegand M, Lindhorst TK. 2006. Synthesis of cluster mannosides
carrying a photolabile diazirine group. Eur J Org Chem:719–728.
Wang H-W, Liu Y-Q, Feng C-G. 2006. Isolation and identification of a novel
flavonoid from Penthorum chinense P. J Asian Nat Prod Res 8:757–761.
Wang J, Li J, Chen H-N, Chang H, Tanifum CT, Liu H-H, Czyryca PG, Chang
C-WT. 2005a. Glycodiversification for the optimization of the
kanamycin class aminoglycosides. J Med Chem 48:6271–6285.
Wang J, Mou H, Jiang X, Guan H. 2006a. Characterization of a novel betaagarase from marine Alteromonas sp. SY37-12 and its degrading
products. Appl Microbiol Biotechnol 71:833–839.
Wang X, McGrath SC, Cotter RJ, Raetz CRH. 2006b. Expression cloning and
periplasmic orientation of the Francisella novicida Lipid A 40 phosphatase LpxF. J Biol Chem 281:9321–9330.
Wang X, Ribeiro AA, Guan Z, McGrath SC, Cotter RJ, Raetz CRH. 2006c.
Structure and biosynthesis of free lipid A molecules that replace
lipopolysaccharide in Francisella tularensis subsp. novicida. Biochemistry 45:14427–14440.
Wang Y, Han F, Hu B, Li J, Yu W. 2006d. In vivo prebiotic properties of
alginate oligosaccharides prepared through enzymatic hydrolysis of
alginate. Nutr Res 26:597–603.
Wang Y, Yan Q, Wu J, Zhang L-H, Ye X-S. 2005b. A new one-pot synthesis of
a-Gal epitope derivatives involved in the hyperacute rejection response
in xenotransplantation. Tetrahedron 61:4313–4321.
Warabi K, Hamada T, Nakao Y, Matsunaga S, Hirota H, van Soest RWM,
Fusetani N. 2005. Axinelloside A, an unprecedented highly sulfated
lipopolysaccharide inhibiting telomerase, from the marine sponge,
Axinella infundibula. J Am Chem Soc 127:13262–13270.
Ward RE, Ninonuevo M, Mills DA, Lebrilla CB, German JB. 2006. In vitro
fermentation of breast milk oligosaccharides by Bifidobacterium
infantis and Lactobacillus gasseri. Appl Environ Microbiol 72:4497–
4499.
Warnock D, Bai X, Autote K, Gonzales J, Kinealy K, Yan B, Qian J,
Stevenson T, Zopf D, Bayer RJ. 2005. In vitro galactosylation of human
IgG at 1 kg scale using recombinant galactosyltransferase. Biotechnol
Bioeng 92:831–842.
98
Webber D, Radcliffe CM, Royle L, Tobiasen G, Merry AH, Rodgers AL,
Sturrock ED, Wormald MR, Harvey DJ, Dwek RA, Rudd PM. 2006.
Sialylation of urinary prothrombin fragment 1 is implicated as a
contributory factor in the risk of calcium oxalate kidney stone
formation. FASEB J 273:3024–3037.
Weerapana E, Glover KJ, Chen MM, Imperiali B. 2005. Investigating
bacterial N-linked glycosylation: Synthesis and glycosyl acceptor
activity of the undecaprenyl pyrophosphate-linked bacillosamine. J Am
Chem Soc 127:13766–13767.
Wei L, Wei G, Zhang H, Wang PG, Du Y. 2005a. Synthesis of new,
potent avermectin-like insecticidal agents. Carbohydr Res 340:1583–
1590.
Wei Y, Yen TY, Cai J, Trent JO, Pierce WM, Young WW. 2005b. Structural
features of the lysosomal hydrolase mannose 6-phosphate uncovering
enzyme. Glycoconj J 22:13–19.
Weimer PJ, Price NPJ, Kroukamp O, Joubert L-M, Wolfaardt GM, Van Zyl
WH. 2006. Studies of the extracellular glycocalyx of the anaerobic
cellulolytic bacterium Ruminococcus albus 7. Appl Environ Microbiol
72:7559–7566.
Westerlind U, Norberg T. 2006. Chemical synthesis of analogs of the
glycopeptide contulakin-G, an analgetically active conopeptide from
Conus geographus. Carbohydr Res 341:9–18.
Wilson JC, Hitchen PG, Frank M, Peak IR, Collins PM, Morris HR, Dell A,
Grice ID. 2005. Identification of a capsular polysaccharide from
Moraxella bovis. Carbohydr Res 340:765–769.
Wolfenden ML, Cloninger MJ. 2005. Mannose/glucose-functionalized
dendrimers to investigate the predictable tunability of multivalent
interactions. J Am Chem Soc 127:12168–12169.
Wolfenden ML, Cloninger MJ. 2006. Carbohydrate-functionalized dendrimers to investigate the predictable tunability of multivalent
interactions. Bioconjug Chem 17:958–966.
Wong C-H. 2005. Protein glycosylation: New challenges and opportunities. J
Org Chem 70:4219–4225.
Wong NSC, Yap MGS, Wang DIC. 2006. Enhancing recombinant
glycoprotein sialylation through CMP-sialic acid transporter over
expression in Chinese hamster ovary cells. Biotechnol Bioeng 93:
1005–1016.
Woosley B, Xie M, Wells L, Orlando R, Garrison D, King D,
Bergmann C. 2006a. Comprehensive glycan analysis of recombinant
Aspergillus niger endo-polygalacturonase C. Anal Biochem 354:43–
53.
Woosley BD, Kim YH, Kolli VSK, Wells L, King D, Poe R, Orlando R,
Bergmann C. 2006b. Glycan analysis of recombinant Aspergillus niger
endo-polygalacturonase A. Carbohydr Res 341:2370–2378.
Wopereis S, Morava E, Grünewald S, Mills PB, Winchester BG, Clayton P,
Coucke P, Huijben KMLC, Wevers RA. 2005. A combined defect in the
biosynthesis of N- and O-glycans in patients with cutis laxa and
neurological involvement: The biochemical characteristics. Biochim
Biophys Acta 1741:156–164.
Wu P, Malkoch M, Hunt JN, Vestberg R, Kaltgrad E, Finn MG, Fokin VV,
Sharpless BS, Hawker CJ. 2005. Multivalent, bifunctional dendrimers
prepared by click chemistry. Chem Commun:5775–5777.
Wu X, Bundle DR. 2005. Synthesis of glycoconjugate vaccines for Candida
albicans using novel linker methodology. J Org Chem 70:7381–
7388.
Wuhrer M, Balog CIA, Catalina MI, Jones FM, Schramm G, Haas H,
Doenhoff MJ, Dunne DW, Deelder AM, Hokke CH. 2006a. IPSE/alpha1, a major secretory glycoprotein antigen from schistosome eggs,
expresses the Lewis X motif on core-difucosylated N-glycans. FEBS J
273:2276–2292.
Wuhrer M, Balog CIA, Koeleman CAM, Deelder AM, Hokke CH. 2005. New
features of site-specific horseradish peroxidase (HRP) glycosylation
uncovered by nano-LC-MS with repeated ion-isolation/fragmentation
cycles. Biochim Biophys Acta 1723:229–239.
Mass Spectrometry Reviews DOI 10.1002/mas
ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES
Wuhrer M, Deelder AM. 2005. Negative-mode MALDI-TOF/TOF-MS of
oligosaccharides labeled with 2-aminobenzamide. Anal Chem
77:6954–6959.
Wuhrer M, Deelder AM. 2006. Matrix-assisted laser desorption/ionization insource decay combined with tandem time-of-flight mass spectrometry
of permethylated oligosaccharides: Targeted characterization of
specific parts of the glycan structure. Rapid Commun Mass Spectrom
20:943–951.
Wuhrer M, Koeleman CA, Deelder AM, Hokke CH. 2006b. Repeats of
LacdiNAc and fucosylated LacdiNAc on N-glycans of the human
parasite Schistosoma mansoni. FEBS J 273:347–361.
Wuhrer M, Koeleman CA, Hokke CH, Deelder AM. 2006c. Mass
spectrometry of proton adducts of fucosylated N-glycans: Fucose
transfer between antennae gives rise to misleading fragments. Rapid
Commun Mass Spectrom 20:1747–1754.
Wuhrer M, Koeleman CAM, Fitzpatrick JM, Hoffmann KF, Deelder AD,
Hokke CH. 2006d. Gender-specific expression of complex-type Nglycans in schistosomes. Glycobiology 16:991–1006.
Wyatt MF, Stein BK, Brenton AG. 2006. Characterization of various analytes
using matrix-assisted laser desorption/ionization time-of-flight mass
spectrometry and 2-[(2E)-3-(4-tert-butylphenyl)-2-methylprop-2-enylidene]malononitrile matrix. Anal Chem 78:199–206.
Xia B, Kawar ZS, Ju T, Alvarez RA, Sachdev GP, Cummings RD. 2005a.
Versatile fluorescent derivatization of glycans for glycomic analysis.
Nat Methods 2:845–850.
Xia B, Royall JA, Damera G, Sachdev GP, Cummings RD. 2005b. Altered Oglycosylation and sulfation of airway mucins associated with cystic
fibrosis. Glycobiology 15:747–775.
Xiao Z, Prieto D, Conrads TP, Veenstra TD, Issaq HJ. 2005. Proteomic
patterns: Their potential for disease diagnosis. Mol Cell Endocrinol
230:95–106.
Xie B, Zhou G, Chan S-Y, Shapiro E, Kong X-P, Wu X-R, Sun T-T, Costello
CE. 2006. Distinct glycan structures of uroplakins Ia and Ib: Structural
basis for the selective binding of FimH adhesin to uroplakin Ia. J Biol
Chem 281:14644–14653.
Xing G-W, Wu D, Poles MA, Horowitz A, Tsuji M, Ho DD, Wong C-H. 2005.
Synthesis and human NKT cell stimulating properties of 3-O-sulfo-a/bgalactosylceramides. Bioorg Med Chem 13:2907–2916.
Xu S, Li Y, Zou H, Qiu J, Guo Z, Guo B. 2003. Carbon nanotubes as assisted
matrix for laser desorption/ionization time-of-flight mass spectrometry.
Anal Chem 75:6191–6195.
Xue J, Zhu J, Marchant RE, Guo Z. 2005. Pentaerythritol as the core of
multivalent glycolipids: Synthesis of a glycolipid with three SO3Lea
ligands. Org Lett 7:3753–3756.
Yagi H, Takahashi N, Yamaguchi Y, Kimura N, Uchimura K, Kannagi R, Kato
K. 2005. Development of structural analysis of sulfated N-glycans by
multidimensional high performance liquid chromatography mapping
methods. Glycobiology 15:1051–1060.
Yamagaki T. 2005. Development of structure analysis method of isomeric
oligosaccharides by MALDI-TOF mass spectrometry. Bunseki Kagaku
54:983–990.
Yamagaki T, Fukui K, Tachibana K. 2006. Analysis of glycosyl bond cleavage
and related isotope effects in collision-induced dissociation quadrupole-time-of-flight mass spectrometry of isomeric trehaloses. Anal
Chem 78:1015–1022.
Yamagaki T, Suzuki H, Tachibana K. 2005. In-source and postsource decay in
negative-ion matrix-assisted laser desorption/ionization time-of-flight
mass spectrometry of neutral oligosaccharides. Anal Chem 77:1701–
1707.
Yamagaki T, Suzuki H, Tachibana K. 2006a. A comparative study of the
fragmentation of neutral lactooligosaccharides in negative-ion mode by
UV-MALDI-TOF and UV-MALDI ion-trap/TOF mass spectrometry. J
Am Soc Mass Spectrom 17:67–74.
Mass Spectrometry Reviews DOI 10.1002/mas
&
Yamagaki T, Suzuki H, Tachibana K. 2006b. Semiquantitative analysis of
isomeric oligosaccharides by negative-ion mode UV-MALDI TOF
postsource decay mass spectrometry and their fragmentation mechanism study at N-acetyl hexosamine moiety. J Mass Spectrom 41:454–
462.
Yamagaki T, Suzuki H, Tachibana K. 2006c. Study of negative-ion MALDIMS of neutral oligosaccharides I: Linkage isomers’ analyses by
postsource and in-source decay measurements. J Mass Spectrom Soc
Jpn 54:141–149.
Yamaguchi M, Kojima K, Hayashi N, Kakizaki I, Kon A, Takagaki K. 2006.
Efficient and widely applicable method of constructing neo-proteoglycan utilizing copper(I) catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett 47:7455–7458.
Yamamoto N, Takayanagi A, Sakakibara T, Dawson PE, Kajihara Y.
2006. Highly efficient synthesis of sialylglycopeptides overcoming
unexpected aspartimide formation during activation of FmocAsn(undecadisialyloligosaccharide)-OH. Tetrahedron Lett 47:1341–
1346.
Yamamoto S, Muramatsu H, Muramatsu T. 2005. Mutational studies on endob-N-acetylglucosaminidase D which hydrolyzes core portion of
asparagine-linked complex type oligosaccharides. Glycoconj J 22:
35–42.
Yamanoi T, Yoshida N, Oda Y, Akaike E, Tsutsumida M, Kobayashi N, Osumi
K, Yamamoto K, Fujita K, Takahashi K, Hattori K. 2005. Synthesis of
mono-glucose-branched cyclodextrins with a high inclusion ability for
doxorubicin and their efficient glycosylation using Mucor hiemalis
endo-b-N-acetylglucosaminidase. Bioorg Med Chem Lett 15:1009–
1013.
Yang Y-L, Yang F-L, Jao S-C, Chen M-Y, Tsay S-S, Zou W, Wu S-H. 2006.
Structural elucidation of phosphoglycolipids from strains of the
bacterial thermophiles Thermus and Meiothermus. J Lipid Res 47:
1823–1832.
Yang Z, Wong EL-M, Shum TY-T, Che C-M, Hui Y. 2005. Fluorophoreappended steroidal saponin (dioscin and polyphyllin D) derivatives. Org
Lett 7:669–672.
Yaoi K, Kondo H, Noro N, Suzuki M, Tsuda S, Mitsuishi Y. 2005a. Functions
and structures of xyloglucan hydrolyases belonging to glycoside
hydrolyse family 74. J Appl Glycosci 52:169–176.
Yaoi K, Nakai T, Kameda Y, Hiyoshi A, Mitsuishi Y. 2005b. Cloning and
characterization of two xyloglucanases from Paenibacillus sp. strain
KM21. Appl Environ Microbiol 71:7670–7678.
Yashunsky DV, Borodkin VS, Ferguson MAJ, Nikolaev AV. 2006. The
chemical synthesis of bioactive glycosylphosphatidylinositols from
Trypanosoma cruzi containing an unsaturated fatty acid in the lipid.
Angew Chem Int Ed Engl 45:468–474.
Yasuda J, Eguchi H, Fujiwara N, Ookawara T, Kojima S, Yamaguchi Y,
Nishimura M, Fujimoto J, Suzuki K. 2006. Reactive oxygen species
modify oligosaccharides of glycoproteins in vivo: A study of a
spontaneous acute hepatitis model rat (LEC rat). Biochem Biophys
Res Commun 342:127–134.
Ye X-S, Sun F, Liu M, Li Q, Wang Y, Zhang G, Zhang L-H, Zhang X-L. 2005.
Synthetic iminosugar derivatives as new potential immunosuppressive
agents. J Med Chem 48:3688–3691.
Yeager AR, Finney NS. 2005. Synthesis of fluorescently labeled UDPGlcNAc analogues and their evaluation as chitin synthase substrates. J
Org Chem 70:1269–1275.
Ying L, Liu R, Zhang J, Lam K, Lebrilla CB, Gervay-Hague J. 2005. A
topologically segregated one-bead-one-compound combinatorial glycopeptide library for identification of lectin ligands. J Comb Chem
7:372–384.
Yonezawa N, Kudo K, Terauchi H, Kanai S, Yoda N, Tanokura M,
Ito K, Miura K, Katsumata T, Nakano M. 2005. Recombinant
porcine zona pellucida glycoproteins expressed in Sf9 cells bind to
99
&
HARVEY
bovine sperm but not to porcine sperm. J Biol Chem 280:20189–
20196.
Yoon SJ, Nakayama K-I, Takahashi N, Yagi H, Utkina N, Wang HY, Kato K,
Sadilek M, Hakomori S-I. 2006. Interaction of N-linked glycans, having
multivalent GlcNAc termini, with GM3 ganglioside. Glycoconj J
23:639–649.
Yoshida N, Takatsuka K, Katsuragi T, Tani Y. 2005. Occurrence of fructosylamino acid oxidase-reactive compounds in fungal cells. Biosci
Biotechnol Biochem 69:258–260.
Yu B, Cong H, Liu H, Li Y, Liu F. 2005a. Ionene-dynamically coated capillary
for analysis of urinary and recombinant human erythropoietin by
capillary electrophoresis and online electrospray ionization mass
spectrometry. J Sep Sci 28:2390–2400.
Yu F, Prestegard JH. 2006. Structural monitoring of oligosaccharides through
13
C enrichment and NMR observation of acetyl groups. Biophys J
91:1952–1959.
Yu H, Teramoto A, Fukudome M, Xie R-G, Yuan D-Q, Fujita K. 2006. A
facile sulfonylation method enabling direct syntheses of per(2-Osulfonyl)-b-cyclodextrins. Tetrahedron Lett 47:8837–8840.
Yu SY, Wu SW, Khoo KH. 2006. Distinctive characteristics of MALDI-Q/
TOF and TOF/TOF tandem mass spectrometry for sequencing of
permethylated complex type N-glycans. Glycoconj J 23:355–369.
Yu YG, Gilar M, Kaska J, Gebler JC. 2005b. Deglycosylation and sample
cleanup method for mass spectrometry analysis of N-linked glycans. LC
GC North America:23–25.
Yu YQ, Gilar M, Kaska J, Gebler JC. 2005c. A rapid sample preparation
method for mass spectrometric characterization of N-linked glycans.
Rapid Commun Mass Spectrom 19:2331–2336.
Yurkova I, Kisel M, Arnhold J, Shadyro O. 2005. Free-radical fragmentation
of galactocerebrosides: A MALDI-TOF mass spectrometry study.
Chem Phys Lipids 134:41–49.
Zaliz CLR, Erra-Balsells R, Nonami H, Sato Y, Varela O. 2005. Synthesis and
polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives. Arkivoc:76–87.
Zaliz CLR, Varela O. 2006. Facile synthesis of a D-galactono-1,6-lactone
derivative, a precursor of a copolyester. Carbohydr Res 341:2973–
2977.
Zandleven J, Beldman G, Bosveld M, Benen J, Voragen A. 2006a. Mode of
action of xylogalacturonan hydrolase towards xylogalacturonan and
xylogalacturonan oligosaccharides. Biochem J 387:719–725.
Zandleven J, Beldman G, Bosveld M, Schols HA, Voragen AGJ. 2006b.
Enzymatic degradation studies of xylogalacturonans from apple and
potato, using xylogalacturonan hydrolase. Carbohydr Polym 65:495–503.
Zehl M, Pittenauer E, Rizzi A, Allmaier G. 2006. Characterization of
moenomycin antibiotic complex by multistage MALDI-IT/RTOF-MS
and ESI-IT-MS. J Am Soc Mass Spectrom 17:1081–1090.
Zeleny R, Leonard R, Dorfner G, Dalik T, Kolarich D, Altmann F. 2006.
Molecular cloning and characterization of a plant a,3/4-fucosidase
based on sequence tags from almond fucosidase I. Phytochemistry
67:641–648.
Zhang G, Fu M, Ning J. 2005a. First synthesis of 5,6-branched galactohexasaccharide, the dimer of the trisaccharide repeating unit of the cellwall galactans of Bifidobacterium catenulatum YIT 4016. Tetrahedron
Asym 16:733–738.
Zhang G, Fu M, Ning J. 2005b. Synthesis of galactose-containing analogues
of (1-6)-branched (1-3)-glucohexaose and its lauryl glycoside.
Carbohydr Res 340:597–602.
Zhang H, Singh S, Reinhold VN. 2005. Congruent strategies for carbohydrate
sequencing. 2. FragLib: An MSn spectral library. Anal Chem 77:6263–
6270.
Zhang J, LaMotte L, Dodds ED, Lebrilla CB. 2005c. Atmospheric pressure
MALDI Fourier transform mass spectrometry of labile oligosaccharides. Anal Chem 77:4429–4438.
100
Zhang J, Schubothe K, Li B, Russell S, Lebrilla CB. 2005d. Infrared
multiphoton dissociation of O-linked mucin-type oligosaccharides.
Anal Chem 77:208–214.
Zhang M, Shi Z, Bai Y, Gao Y, Hu R, Zhao F. 2006. Using molecular
recognition of b-cyclodextrin to determine molecular weights of lowmolecular-weight explosives by MALDI-TOF mass spectrometry. J Am
Soc Mass Spectrom 17:189–193.
Zhao J, Simeone DM, Heidt D, Anderson MA, Lubman DM. 2006.
Comparative serum glycoproteomics using lectin selected sialic acid
glycoproteins with mass spectrometric analysis: Application to
pancreatic cancer serum. J Proteome Res 5:1792–1802.
Zhao W, Kong F. 2005. Facile synthesis of the heptasaccharide repeating unit
of O-deacetylated GXM of C. neoformans serotype B. Bioorg Med
Chem 13:121–130.
Zheng W, Kollmeyer J, Symolon H, Momin A, Munter E, Wang E, Kelly S,
Allegood JC, Liu Y, Peng Q, Ramaraju H, Sullards MC, Cabot M,
Merrill AHJ. 2006. Ceramides and other bioactive sphingolipid
backbones in health and disease: Lipidomic analysis, metabolism and
roles in membrane structure, dynamics, signaling and autophagy.
Biochim Biophys Acta 1758:1864–1884.
Zheng X, Wu S-L, Hancock WS. 2006. Glycation of interferon-beta-1b and
human serum albumin in a lyophilized glucose formulation: Part III:
Application of proteomic analysis to the manufacture of biological
drugs. Int J Pharm 322:136–145.
Zhong R, Peña MJ, Zhou G-K, Nairn CJ, Wood-Jones A, Richardson EA,
Morrison WH III, Darvill AG, York WS, Ye Z-H. 2005. Arabidopsis
Fragile Fiber8, which encodes a putative glucuronyltransferase, is
essential for normal secondary wall synthesis. Plant Cell 17:3390–3408.
Zhou Q, Kyazike J, Echelard Y, Meade HM, Higgins E, Cole ES, Edmunds T.
2005. Effect of genetic background on glycosylation heterogeneity in
human antithrombin produced in the mammary gland of transgenic
goats. J Biotechnol 117:57–72.
Zhu J, Marchant RE. 2006. Dendritic saccharide surfactant polymers as
antifouling interface materials to reduce platelet adhesion. Biomacromolecules 7:1036–1041.
Zhu J, Yan F, Guo Z, Marchant RE. 2005a. Surface modification of liposomes
by saccharides: Vesicle size and stability of lactosyl liposomes studied by
photon correlation spectroscopy. J Colloid Interface Sci 289:542–550.
Zhu L, van de Lavoir M-C, Albanese J, Beenhouwer DO, Cardarelli PM,
Cuison S, Deng DF, Deshpande S, Diamond JH, Green L, Halk EL,
Heyer BS, Kay RM, Kerchner A, Leighton PA, Mather CM, Morrison
SL, Nikolov ZL, Passmore DB, Pradas-Monne A, Preston BT, Rangan
VS, Shi M, Srinivasan M, White SG, Winters-Digiacinto P, Wong S,
Zhou W, Etches RJ. 2005b. Production of human monoclonal antibody
in eggs of chimeric chickens. Nat Biotechnol 23:1159–1169.
Zhu P, Boykins RA, Tsai C-M. 2006. Genetic and functional analyses of the
IgtH gene, a member of the b-1,4-galactosyltransferase gene family in
the genus Neisseria. Microbiology 152:123–134.
Zhu S, Shimokawa S, Shoyama Y, Tanaka H. 2006a. A novel analytical
ELISA-based methodology for pharmacologically active saikosaponins. Fitoterapia 77:100–108.
Zhu S, Zhang Y, Li M, Yu J, Zhang L, Li Y, Yu B. 2006b. Synthesis and
cytotoxicities of dioscin derivatives with decorated chacotriosyl
residues. Bioorg Med Chem Lett 16:5629–5632.
Zhu X, Kawatkar S, Rao Y, Geert-Jan Boons G-J. 2006c. Practical approach
for the stereoselective introduction of b-arabinofuranosides. J Am
Chem Soc 128:11948–11957.
Ziegler T, Schips C. 2006. An efficient Mitsunobu protocol for the one-pot
synthesis of S-glycosyl amino-acid building blocks and their use in
combinatorial spot synthesis of glycopeptide libraries. Nat Protoc
1:1987–1994.
Zou K, Tong W-Y, Liang H, Cui J-R, Tu G-Z, Zhao Y-Y, Zhang R-Y. 2005.
Diastereoisomeric saponins from Albizia julibrissin. Carbohydr Res
340:1329–1334.
Mass Spectrometry Reviews DOI 10.1002/mas