Synthesis of variously sulfated biotinylated oligosaccharides from the linkage region of proteoglycans.

The synthesis of a collection, as biotinylated conjugates, of various sulfoforms of the trisaccharide β-D-GlcpA-(1→3)-β-D-Galp-(1→3)-β-D-Galp, structures encountered in the linkage region of proteoglycans, is reported herein for the first time. An efficient and stereocontrolled preparation was achieved using common key intermediates in a divergent manner. These molecules should be useful probes to study the substrate specificity of the glycosyltransferases involved at the bifurcation point in the biosynthesis of proteoglycans.