Synthesis and characterization of novel glycopolymers based on ethyl α-hydroxymethylacrylate

Novel methacrylate derivatives bearing beta-D-glucopyranoside and beta-D-galactopyranoside residues are synthesized. The construction of the corresponding glycosidic linkages are performed using 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide and 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide as glycosyl donors, with ethyl alpha-hydroxymethylacrylate. New glycopolymers are obtained by homo, and copolymerization with methyl methacrylate of the corresponding glycomonomers. The reactivity ratios of two protected copolymer systems are determined. Deprotected monomers and polymers are further obtained and characterized by treatment with sodium methoxide. The binding of deprotected polymer with galactose residues to specific receptor protein (RCA(120)) is achieved. (c) 2006 Elsevier Ltd. All rights reserved.