Issue 34, 2017

The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity

Abstract

The first total synthesis of a polypeptin, PE2, as well as its solution structure is reported. Synthesis in optically pure form confirms the proposed stereochemistry of the polypeptins at the 3-position on the 3-hydroxy depsipeptide moiety. We have also determined the NMR structure of PE2 in aqueous solution, showing it to form a stable ring conformation. The synthetic peptide shows anti-bacterial activity consistent with reports for naturally derived counterparts.

Graphical abstract: The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity

Supplementary files

Article information

Article type
Paper
Submitted
21 Jun 2017
Accepted
07 Aug 2017
First published
07 Aug 2017

Org. Biomol. Chem., 2017,15, 7173-7180

The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity

S. J. Mountford, B. Mohanty, K. D. Roberts, H. H. Yu, M. J. Scanlon, R. L. Nation, T. Velkov, J. Li and P. E. Thompson, Org. Biomol. Chem., 2017, 15, 7173 DOI: 10.1039/C7OB01493G

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