Synthesis of glycopeptide-conjugates via ring-opening polymerization of sugar-substituted α-amino acid N-carboxyanhydrides (GlycoNCAs)

Abstract

This article briefly reviews our recent investigation on the synthesis and biological functions of artificial glycopeptide-conjugates via ring-opening polymerization of D-glucose- or N-acetyl-D-glucosamine-substituted L-serine N-carboxyanhydrides (glycoNCAs). Primary amine-initiated polymerization of glycoNCAs proceeded without side reactions to give linear glycopeptide-conjugates of controlled chain lengths. A variety of block copolymers and graft copolymers containing glycopeptide segments were synthesized by utilizing the living nature of the ring-opening polymerization of glycoNCAs. Reaction of primary amine-terminated poly(amido amine) dendrimers of different generations with a slight excess of glycoNCAs at -30°C gave a new type of dendrimers whose surfaces were modified with the corresponding mono(glycopeptide) moieties. Oligomerization of glycoNCAs with poly(amido amine) dendrimer as a multifunctional macroinitiator at 27°C provided globular macromolecules coated with oligo(glycopeptide) chains. Molecular recognition abilities of these linear and globular glycopeptide-conjugate macromolecules were evaluated by the hemagglutination inhibition assay.