Non-natural carbohydrate-bearing polymers are emerging as important materials for the investigation of multivalent carbohydrate-protein interactions. In the present study, neoglycopolymers were generated via aqueous ring-opening metathesis polymerizations. A procedure employing a ruthenium catalyst, preformed by treating a small quantity of the monomer with RuCl3, reduced metal contamination in the products. To examine the effect of sugar residue density on polymer function, materials bearing one or two sugar ligands per repeat unit were synthesized. These polymers were tested for their ability to inhibit the erythrocyte agglutinating activity of the carbohydrate-binding protein, concanavalin A. The polymers with lower sugar density were found to be more potent inhibitors than polymers with higher density, a result that can be rationalized by analysis of the protein and polymer structures.
Bibliographical noteFunding Information:
This research was supported in part by the National Institutes of Health (GM-49975). L.L.K. thanks the NSF National Young Investigator Program, the Beckman Young Investigator Program, the American Cancer Society (Junior Faculty Award) and the Milwaukee Foundation (Shaw Scientist Program) for support. M.C.S. is a student in the UW-Madison M.D./Ph.D. Integrated Degree Program. K.H.M. acknowledges the Upjohn Company (ACS Division of Organic Chemistry fellow-
ship) and the N.1.H (Chemistry-Biology Interface, T32 GM085051 for predoctoral fellowships. ADH thanks the N.I.H. for a predoctoral fellowship (Molecular Biosciences, T32 GMO7215). We thank Dr. C. Fry (UW-Madison, Chemistry Instrument Center) for helpful discussions and J. Van Stelle (UW-Madison, Animal Care Facility) for assistance obtaining rabbit erythrocytes.
- Aqueous ring-opening metathesis polymerization
- Concanavalin A