Polypeptides with domains of sugar modified residues have many potential biomedical applications in glycomics research, drug delivery, and tissue engineering. Three peracetylated monosaccharide-linked lysine N-carboxyanhydride (NCA) monomers have been synthesized and polymerized using tetrakis(trimethylphosphine)cobalt(0). Polymerization studies have demonstrated that these NCAs display the characteristics of controlled and living polymerization such as control over molecular weight by varying the monomer to initiator ratio, and preparation of statistical and block copolymers. All deacetylated glycopolypeptides studied are fully water soluble. The aqueous conformation of the glycosylated polylysine was examined using circular dichroism spectroscopy. The glycopeptides were found to take on a highly alpha-helical content in water that is stable over a wide temperature range. Highly helical, non-ionic polypeptide segments are useful building blocks in self-assembled polypeptide structures. Current studies are underway on glyconjugates featuring covalent linkages to various  amino acids, with various aqueous conformations.

Glycosylated polypeptides by ring opening polymerization of glycosylated N-carboxyanhydrides

243rd National Meeting (2012)

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