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J Am Chem Soc. 2010 Oct 27;132(42):15068-71. doi: 10.1021/ja107425f.

Glycopolypeptides via living polymerization of glycosylated-L-lysine N-carboxyanhydrides.

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  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1600, United States.


The preparation of new glycosylated-L-lysine-N-carboxyanhydride (glyco-K NCA) monomers is described. These monomers employ C-linked sugars and amide linkages to lysine for improved stability without sacrificing biochemical properties. Three glyco-K NCAs were synthesized, purified, and found to undergo living polymerization using transition metal initiation. These are the first living polymerizations of glycosylated NCAs and were used to prepare well-defined, high molecular weight glycopolypeptides and block and statistical glycocopolypeptides. This methodology solves many long-standing problems in the direct synthesis of glycopolypeptides from N-carboxyanhydrides relating to monomer synthesis, purification, and polymerization and gives polypeptides with 100% glycosylation. These long chain glycopolypeptides have potential to be good mimics of natural high molecular weight glycoproteins.

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