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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► The trisaccharide backbone was constructed starting from the non-reducing end. ► One trisaccharide diol derivative was fully resistant to benzoylation. ► Biotinylated derivatives were prepared from oligomer precursors having a masked amine group at the reducing anomeric carbon.