Synthetic mimics of carbohydrate-based anticancer vaccines: preparation of carbohydrate polymers bearing unimolecular trivalent carbohydrate ligands by controlled living radical polymerization

Abstract

Synthetic methods for preparation of three different styrene-type carbohydrate monomers, containing mannose, sialic acid and N-acetyllactosamine were successfully developed. Diethylene glycol was used as the spacer between the styrene and carbohydrate moieties. Under the conditions of nitroxide-mediated polymerizations, controlled living radical polymerizations could be accomplished, affording well defined carbohydrate polymers with different sugar compositions. The PDIs were increased and conversions were decreased upon increasing the concentrations of carbohydrate monomers. The resulting carbohydrate polymers were characterized by NMR. Novel carbohydrate polymers bearing unimolecular trivalent carbohydrate ligands could also be achieved through the living radical process used in this study.