Protecting-group-free synthesis of well-defined glycopolymers featuring negatively charged oligosaccharides

Abstract

Control of the macromolecular architecture is essential to enable sophisticated functions for glycopolymers and to allow a precise correlation between these functions and the polymer structure. A number of biologically important ligands are negatively charged oligosaccharides that are difficult to manipulate in organic solvent and that are hardly amenable to protection/deprotection strategies. RAFT polymerization is a simple and robust technique that enables the synthesis of well-defined glycopolymers directly in aqueous solution and starting from unprotected vinyl glycomonomers. Here I describe how RAFT polymerization can be combined with reductive amination to transform negatively charged oligosaccharides having 5–20 monosaccharide units into well-defined glycopolymers directly in water and without the need to resort to protecting-group chemistry.