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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 (6-deoxy-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 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. Ever-increasing 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 Mittelstand, engl. Central Innovation Programme for SMEs) project fund. "Small and medium-sized 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.

Website address: https://www.gesundheitsindustrie-bw.de/en/article/news/new-synthesis-method-produces-compound-for-use-in-tumour-medicines