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

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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

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Publication details

The article was received on 21 Jun 2017, accepted on 07 Aug 2017 and first published on 07 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01493G
Citation: Org. Biomol. Chem., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB01493G

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