Synthesis of oligosaccharides of glycosaminoglycans using semisynthesis strategy
Challenge : Development of new synthetic methodologies in chondroitin sulfate (CS) and hyaluronic acid series - Structure-function study of the chondroitin synthase, glycosyltransferase responsible of the CS chains polymerization – Study of GAGs-lectins interaction.
We developed an efficient and competitive process using semisynthesis starting from commercialy available CS polymer for the preparation of oligosaccharides of GAG oligosaccharides. Acid hydrolysis of the natural polymer affords a key disaccharide building block which possesses the functionalities of chondrosine, the basic repeating unit of CS. This disaccharide, obtained on multi-gram scale, is the starting building block for the preparation of a large collection of chondroitin sulfate or hyaluronic acid oligosaccharides.
Example of sulfated and biotinylated oligosaccharide :
Multidisciplinary program supported by :
- ANR BLAN 2008 « Glycocart »
- Projet Centre-FEDER « glycosign » with Glycodiag company