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.

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

Cite this

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title = "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.",
author = "Mountford, {Simon J.} and Biswaranjan Mohanty and Roberts, {Kade D.} and Yu, {Heidi H.} and Scanlon, {Martin J.} and Nation, {Roger L.} and Tony Velkov and Jian Li and Thompson, {Philp E.}",
year = "2017",
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language = "English",
volume = "15",
pages = "7173--7180",
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publisher = "The Royal Society of Chemistry",
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T1 - The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity

AU - Mountford, Simon J.

AU - Mohanty, Biswaranjan

AU - Roberts, Kade D.

AU - Yu, Heidi H.

AU - Scanlon, Martin J.

AU - Nation, Roger L.

AU - Velkov, Tony

AU - Li, Jian

AU - Thompson, Philp E.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

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U2 - 10.1039/c7ob01493g

DO - 10.1039/c7ob01493g

M3 - Article

VL - 15

SP - 7173

EP - 7180

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 34

ER -