Glycosylated polymers are increasingly investigated as synthetic analogs of proteoglycans for their therapeutic and diagnostic potentials. Majority of the glycosylated polymers have carbohydrate epitopes installed on the side-chains, where their density and spacing can be readily adjusted. We investigate the synthesis of helical polypeptide-carbohydrate side-chain conjugates by a combination of controlled polymerizations of N-carboxyanhydride bearing reactive functional side chains (i.e., azido, allyl, propargyl) and click chemistry. Monosaccharide such as mannoses can be readily grafted onto the side-chains of helical polypeptides with high grafting efficiency under mild condition. Polypeptoids featuring an N-substituted polyglycine backbone are structural mimics of polypeptides. Their side-chain conjugates with carbohydrate have been synthesized in a similar manner to the polypeptide conjugates. The solution properties of these polypeptide/polypeptoid-carbohydrate conjugates have been investigated and will be discussed.

Glycosylated polypeptides and polypeptoids: Synthesis and solution properties

243rd National Meeting (2012)

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