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New synthesis method produces compound for use in
tumour medicines
Very few people have ever heard of the chemical compound sulphoquinovose. This natural
substance is nevertheless found in a large variety of foods. Sulphoquinovose has been
playing an increasing role in cancer research, which is why demand for the compound is
constantly growing. With this in mind, researchers from a company called MCAT GmbH from
Konstanz are working on the development a method to synthesise larger quantities of
sulphoquinovose than currently possible.
Sulphoquinovose is a glucose derivative with a sulphonic acid group rather than an OH group
at the sixth carbon (6-deoxy-6-sulphoglucose). It is a building block of sulphoglycolipid
(sulphoquinovosyl diacylglycerol, SQDG), which is a major constituent of the chloroplast cell
membrane and therefore present in many photosynthetic plants. Spinach and green tea
contain particularly large quantities of SQDG. Despite its high bioavailability, pure
sulphoquinovose is difficult to obtain.
Sulphoquinovose is a glucose derivative with a sulphonic acid group rather than an OH group at the sixth carbon (6deoxy-6-sulphoglucose). © MCAT
Current studies are focusing intensively on the biosynthesis, metabolic pathways and
applications of sulphoquinovose and its derivatives. In future, sulphoquinovose will increasingly
be used in cancer research for identifying and studying sulphoquinovose derivatives with an
anti-cancer activity, particularly for their ability to treat tumours. The chemical compound is
also used in cytostatic drug research and the development of new HIV therapeutics, where
sulphoquinovose derivatives are tested for their inhibitory effect on eukaryotic DNA
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polymerases.
What these different research areas have in common is that they require relatively large
quantities of sulphoquinovose and sulphoquinovose derivates to deliver reliable results. Everincreasing quantities of sulphoquinovose are therefore needed to meet demand, which is
particularly high in pharmaceutical research. "Only quite small amounts are currently available.
However, demand is so high that, in the next few years, several kilogrammes, perhaps even up
to 100 kilogrammes a day will have to be produced," says Dr. Magnus Schmidt, Head of
Research, Development and Production at MCAT GmbH.
New synthesis method to meet increasing demand
Dr. Magnus Schmidt is Head of Research, Development and Production at Konstanz-based MCAT GmbH and is in
charge of developing sulphoquinovose synthesis pathways. © private
MCAT GmbH was founded in 1998 as a spin-off from the University of Konstanz. The company
provides life sciences services related to the development and production of catalysts and
organometallic compounds. MCAT GmbH became aware of sulphoquinovose as a potential new
product following a request from a group of researchers at the University of Konstanz who were
attempting to elucidate the biogeochemical sulphur cycle. The bacteria used in this research
required sulphoquinovose as food and sulphur source.
The limited availability of the chemical compound is a major hindrance for such research
activities, and efforts are being made to increase sulphoquinovose yield. Among those working
on the development of effective sulphoquinovose production methods is the Konstanz-based
company, which has already made considerable progress since starting the project in January.
In order to chemically synthesise the compound, the researchers had to study several
synthesis pathways and develop a strategy that yielded small amounts of sulphoquinovose.
Initial yields amounted to several hundred milligrammes.
The next step will be to upscale production and subsequently use the new synthesis strategies
for developing and producing sulphoquinovose derivatives. "We aim to produce quantities of 50
to 100 g in a single production batch," says Schmidt. The researchers have got this far thanks
in part to the support of the German Federal Ministry for Economic Affairs and Energy which is
funding the small company's research through the ZIM (Zentrales Innovatiosprogramm
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Mittelstand, engl. Central Innovation Programme for SMEs) project fund. "Small and mediumsized companies do not have the capacity to finance complex synthesis developments as it is
very difficult to assess the potential added value generated by a project in the ideal case
scenario," says Schmidt. This often means that innovative ideas come to nothing. "The ZIM
programme finally gave us the security we needed to be able to go ahead with the project,"
says Magnus Schmidt.
Quality assurance with nuclear magnetic resonance spectroscopy
A nuclear magnetic resonance spectrometer ensures that synthesised sulphoquinovose is highly pure. © BioLAGO
It will be another year before the company can place the new product on the market. The
process needs to be optimised and high quality standards ensured. In addition to standard
analytical methods, MCAT also uses a nuclear magnetic resonance spectrometer to determine
the purity of the compound. "This is quite remarkable because NMR spectrometers are
relatively expensive. We are probably the smallest company in Germany with access to this
technology in its own laboratories," says Magnus Schmidt. Nuclear magnetic resonance
spectroscopy is particularly suited for detecting impurities in drug substances. The
development of effective sulphoquinovose synthesis methods has led to the identification of
unwanted side products which can subsequently be prevented or eliminated by nuclear
magnetic resonance spectroscopy. "We are able to synthesise sulphoquinovose with a level of
purity that has never before been attained," says Magnus Schmidt with pride.
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Article
30-Sep-2015
Eva Botzenhart-Eggstein
BioLAGO
© BIOPRO Baden-Württemberg GmbH
Further information
MCAT GmbH
Hermann-von-Vicari-Str. 23
D-78464 Konstanz
Tel.: +49(0)7531/939097
E-mail: Schmidt(at)mcat.de
MCAT GmbH,
Konstanz
The article is part of the following dossiers
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