Download DCC-promoted peptide coupling

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DCC
N,N′-Dicyclohexylcarbodiimide
A reagent for coupling and for dehydration
ProductInformation
CAT No
Grade
Application
Storage
C1395
BioXtra, ≥99.0% (GC)
coupling and for dehydration
Room temperature
Product Name:
N,N’-Dicyclohexylcarbodiimide
CAS Number:
538-75-0
Formula:
C6H11N=C=NC6H11
Molecular weight:
206.33
Melting point:
34-35 °C(lit.)
Boiling point
122-124 °C
Synonym:
Carbodicyclohexylimide;Carbodiimide, dicyclohexyl-; Dicyclimide; dicyclohexyl-carbodiimid;
n,n’-dicyclohexylcarbodiimide,1msol.inn-methylpyrrolidone,peptidesynthesisgrade;
n,n’-methan- etetraylbis -cyclohexaamin; n,n’-methanetetraylbis-cyclohexanamin;
N,N’-methanetetraylbis- Cyclohexanamine
Suitability
N,N'-Dicyclohexylcarbodiimide is an organic compound with the chemical formula C13H22N2 whose primary use is to couple
amino acids during artificial peptide synthesis. Under standard conditions, it exists in the form of white crystals with a
heavy, sweet odor. The low melting point of this material allows it to be melted for easy handling. It is highly soluble in
dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water. The compound is often
abbreviated DCC.
DCC is a dehydrating agent for the preparation of amides, ketones, nitriles. In these reactions, DCC hydrates to form
dicyclohexylurea (DCU), a compound that is insoluble in most organic solvents and in water and hence is readily removed by
filtration. DCC can also be used to invert secondary alcohols.
Moffatt oxidation
A solution of DCC and dimethyl sulfoxide (DMSO) effects the so-called Pfitzner-Moffatt oxidation. This procedure is used for
the oxidation of alcohols toaldehydes and ketones. Unlike metal-mediated oxidations, the reaction conditions are
sufficiently mild to avoid over-oxidation of aldehydes to carboxylic acids. Generally, three equivalents of DCC and 0.5
equivalent of proton source in DMSO are allowed to react overnight at room temperature. The reaction is quenched with
acid.
Dehydration
Alcohols can also be dehydrated using DCC. This reaction proceeds by first giving the O-acylurea intermediate which is then
hydrogenolyzed to produce the corresponding alkene:
RCHOHCH2R' + (C6H11N)2C → RCH=CHR' + (C6H11NH)2CO
Inversion of secondary alcohols
Secondary alcohols can be stereochemically inverted by formation of a formyl ester followed by saponification. The
secondary alcohol is mixed directly with DCC, formic acid, and a strong base such as sodium methoxide.
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Esterification
A range of alcohols, including even some tertiary alcohols, can be esterified using a carboxylic acid in the presence of DCC
and a catalytic amount of DMAP.
DCC-promoted peptide coupling
During protein synthesis (such as Fmoc solid-state synthesizers), the N-terminus is often used as the attachment site
on which the amino acid monomers are added. To enhance the electrophilicity of carboxylate group, the negatively
charged oxygen must first be "activated" into a better leaving group. DCC is used for this purpose. The negatively
charged oxygen will act as a nucleophile, attacking the central carbon in DCC. DCC is temporarily attached to the
former carboxylate group forming a highly electrophilic intermediate, making nucleophilic attack by the terminal
amino group on the growing peptide more efficient.
Safety
DCC is a potent allergen and a sensitizer, often causing skin rashes.
Application：
A reagent for coupling and for dehydration
It is also used to modifie bovine heart mitochondrial transhydrogenase, and a inhibitor of F1F0-ATPase and other
proton-translocating enzymes.
Specification
Grade
Purity (GC)
Appearance (Color)
Appearance (Form)
Infrared Spectrum
Proton NMR Spectrum
BioXtra
 99.0 %
White
Powder or Solid or Crystals or Crystalline Chunk(s)or Chunk(s)
Conforms to Structure or Proton NMR Spectrum
Conforms to Structure or Infrared Spectrum
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