title: Glycopolypeptides with a redox-triggered helix-to-coil transition.
abstract: Conformation-switchable glycopolypeptides were prepared by the living polymerization of glycosylated L-cysteine-N-carboxyanhydride (glyco-C NCA) monomers. These new monomers were prepared in high yield by coupling of alkene-terminated C-linked glycosides of D-galactose or D-glucose to L-cysteine using thiol-ene "click" chemistry, followed by their conversion to the corresponding glyco-C NCAs. The resulting glycopolypeptides were found to be water-soluble and α-helical in solution. Aqueous oxidation of the side-chain thioether linkages in these polymers to sulfone groups resulted in disruption of the α-helical conformations without loss of water solubility. The ability to switch chain conformation and remain water-soluble is unprecedented in synthetic polymers, and allows new capabilities to control presentation of sugar functionality in subtly different contexts.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
authors.forename: Jessica R
authors.initials: JR
authors.lastname: Kramer
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Deming
mesh_terms: D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility
chemical_list: D006020:Glycopeptides; D011108:Polymers