Glycopolypeptides with a redox-triggered helix-to-coil transition

Journal of the American Chemical Society
Jessica R Kramer, T J Deming

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.

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Citations

Jan 1, 2013·Faraday Discussions·Colin BonduelleSébastien Lecommandoux
Jul 24, 2013·Biomacromolecules·Colin Bonduelle, Sébastien Lecommandoux
Jan 5, 2014·Chemical Reviews·Fabrice DénèsPhilippe Renaud
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