Glycopolymers have emerged as useful tools to probe glycan based biological interactions and as materials for diverse biomedical applications. Glycosylated polypeptides are particularly attractive polymers since they can display glycans in their native form, naturally form complex secondary structures that drive self-assembly, and are biodegradable. A panel of carbohydrate functionalized polypeptides have been prepared via polymerization of N-carboxyanhydrides. Molecular weight and glycan density can be controlled by polymerization reaction stoichiometry to give glycopolypeptides of biologically-relevant length and composition. The glycopolypeptides are dual end-functionalized with chemical handles that allow conjugation to a variety of substrates and fluorophores. These studies focused on preparation and study of synthetic mucin glycoproteins and synthetic pathogen-associated glycoproteins. Conformation and other physical properties were evaluated. Methods to display the synthetic glycoproteins were examined, such as covalent conjugation to live cell-surfaces or to beads. In particular, functionalization of fluorescent beads allowed study of the impact of carbohydrate composition and density on phagocytosis in a model cell line. We observed increased phagocytosis of glycopolypeptide-bead conjugates bearing canonical pattern-recognition motifs compared to controls. The polypeptides also elicited receptor-dependent cytokine expression in model cell lines. These materials provide a new platform for studying carbohydrate-dependent biological systems.

Polymerization of glycosylated NCAs for preparation of biomedical materials and synthetic glycoproteins

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.