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

Simon J. Mountford, Biswaranjan Mohanty, Kade D. Roberts, Heidi H. Yu, Martin J. Scanlon, Roger L. Nation, Tony Velkov, Jian Li, Philp E. Thompson

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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.

Original languageEnglish
Pages (from-to)7173-7180
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number34
DOIs
Publication statusPublished - 2017

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