Synthesis of glycopeptides from glucosaminic acid

We report on the synthesis of polypeptides with saccharide side chains starting from d-glucosaminic acid. The hydroxyl groups were first protected by benzylation, followed by N-carboxyanhydride formation, which was polymerized by ring opening to form a high molecular weight polyamide. De-protection of the benzyl groups yields a polypeptide with fully de-protected saccharide side chains. The resulting new non-ionic, water soluble, and optically active polymers possessing the properties of both peptides and saccharides have potential use as scaffolds for tissue engineering and drug carriers. The method described here may be extended to any saccharide α-amino acid.