NEOGLYCOPOLYMERS PRODUCED BY AQUEOUS RING-OPENING METATHESIS POLYMERIZATION - DECREASING SACCHARIDE DENSITY INCREASES ACTIVITY

Non-natural carbohydrate-bearing polymers are emerging as important ma terials for the investigation of multivalent carbohydrate-protein inte ractions. In the present study, neoglycopolymers were generated via aq ueous ring-opening metathesis polymerizations. A procedure employing a ruthenium catalyst, preformed by treating a small quantity of the mon omer with RuCl3, reduced metal contamination in the products. To exami ne the effect of sugar residue density on polymer function, materials bearing one or two sugar ligands per repeat unit were synthesized. The se polymers were tested for their ability to inhibit the erythrocyte a gglutinating activity of the carbohydrate-binding protein, concanavali n A. The polymers with lower sugar density were found to be more poten t inhibitors than polymers with higher density, a result that can be r ationalized by analysis of the protein and polymer structures.