Synthesis of thiodisaccharides as inhibitors of glycosidases. Oxidation of the interglycosidic sulfur atom to sulfoxides and sulfones

JUAN P. COLOMER; VERÓNICA E. MANZANO; OSCAR VARELA

Madrid

Simposio; 26 International Carbohydrate Symposium; 2012

Thiooligosaccharides constitute an important class of sulfur analogues of naturally occurring oligosaccharides that are useful tools in glycobiology. They are usually stable to glycosyl hydrolases, in comparison to their natural counterparts, and in many cases they act as inhibitors of these enzymes. We have reported efficient strategies for the construction of the thioglycosidic linkage of thiooligosaccharides, and as part of our continuing interest in this subject, we describe here the synthesis and evaluation of the inhibitory activity of (1->3) and (1->4) thiodisaccharides with terminal glucose or galactose residues. The subsequent oxidation of the sulfur atom of these molecules afforded the respective sulfoxides and sulfones.