Synthesis of glycopolypeptides by the ring opening polymerization of O-glycosylated-α-amino acid N-carboxyanhydride (NCA)

Literature Information

Publication Date 2011-02-16
DOI 10.1039/C0PY00412J
Impact Factor 5.582
Authors

Debasis Pati, Ashif Y. Shaikh, Sayam Sen Gupta


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Abstract

The novel synthesis of O-glycosylated lysine-NCA from a stable glycosyl donor and a commercially available protected amino acid in very high yield is reported. These O-glycosylated lysine-NCA monomers underwent ring opening polymerization using simple primary amine initiators to form well defined, high molecular weight homoglycopolypeptides and diblock co-glycopolypeptides. The synthesis of azide labelled end functionalized glycopolypeptides and amphiphilic diblock copolypeptides is also reported. This methodology represents an easy and practical route to the synthesis of O-glycosylated polypeptides with 100% glycosylation.

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