Synthesis of new glycopolymers containing β-D-mannopyranose, and C-2-substituted β-D-mannopyranose residues as a new class of inhibitor

New styryl monomers containing beta -D-mannopyranose, 2-acetamido-2-deoxy-beta -D-mannopyranose, 2-deoxy-2-fluoro-beta -D-mannopyranose, and 2-deoxy-beta -D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-or-mannosidase digestion. The binding affinity of the carbohydrate polymers obtained from those mannopyranosyl styryl monomers by radical polymerization with Concanavalin A were evaluated. A binding assay indicated that the multivalency effect and the affinity enhancement attained by modification at the C-2 position of the beta -D-mannopyranoside residue resulted in the beta -D-mannopyranosyl polymer which has the same affinity as that of the alpha -D-mannopyranosyl polymer.