Issue 2, 2017

Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

Abstract

We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides based on the intramolecular native chemical ligation of in situ generated thioesters. Key precursors are N-Hnb-Cys crypto-thioesters, easily synthesized by Fmoc-based SPPS. The strategy is applied to a representative range of naturally occurring cyclic disulfide-rich peptide sequences.

Graphical abstract: Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

Supplementary files

Article information

Article type
Communication
Submitted
20 Nov 2016
Accepted
28 Nov 2016
First published
28 Nov 2016

Org. Biomol. Chem., 2017,15, 316-319

Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

V. P. Terrier, A. F. Delmas and V. Aucagne, Org. Biomol. Chem., 2017, 15, 316 DOI: 10.1039/C6OB02546C

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