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 β-D-mannopyranose, 2-acetamido-2-deoxy-β-D-mannopyranose, 2-deoxy-2-fluoro-β-D-mannopyranose, and 2-deoxy-β-D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-α-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 β-D-mannopyranoside residue resulted in the β-D-mannopyranosyl polymer which has the same affinity as that of the α-D-mannopyranosyl polymer.