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.

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► 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.