Stereocontrolled preparation of biotinylated chondroitin sulfate E di-, tetra-, and hexasaccharide conjugates

Abstract

The synthesis of biotinylated conjugates of oligomers of the basic repeating unit of chondroitin sulfate E (CS-E) with the sequence [GlcA-4,6-disulfated GalNAc]n is reported herein for the first time. An efficient and stereocontrolled preparation of di-, tetra-, and hexasaccharide derivatives was achieved using a common key disaccharide intermediate in an iterative way. An unexpected and never reported side reaction on the carbonyl group of the levulinate ester was observed during a coupling reaction. These complex molecules should be useful to study their interactions with various proteins.

Keywords: Biotinylated sugars; Oligosaccharides; Proteoglycans; Sulfoforms.