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Issue 4, 2011
From the journal:

Polymer Chemistry

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

Debasis Pati,a   Ashif Y. Shaikh,b   Srinivas Hotha*bc  and  Sayam Sen Gupta*a  

* Corresponding authors

a CReST, Chemical Engineering Division, National Chemical Laboratory, Pune, India
E-mail: ss.sengupta@ncl.res.in
Fax: +91 20 2590 2021
Tel: +91 20 2590 2747

b Division of Organic Chemistry, National Chemical Laboratory, Pune, India
E-mail: ay.shaikh@ncl.res.in
Tel: +91 20 2590 2331

c Department of Chemistry, Indian Institute of Science Education & Research,
E-mail: s.hotha@iiserpune.ac.in

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.

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

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Article information

DOI
https://doi.org/10.1039/C0PY00412J
Article type
Communication
Submitted
19 Dec 2010
Accepted
17 Jan 2011
First published
16 Feb 2011

Polym. Chem., 2011,2, 805-811

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

D. Pati, A. Y. Shaikh, S. Hotha and S. S. Gupta, Polym. Chem., 2011, 2, 805 DOI: 10.1039/C0PY00412J

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