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

doi:10.1039/c7ob01493g

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

Research output: Contribution to journal › Article › Research › peer-review

3 Citations (Scopus)

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 language	English
Pages (from-to)	7173-7180
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	34
DOIs	https://doi.org/10.1039/c7ob01493g
Publication status	Published - 2017

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10.1039/c7ob01493g

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Mountford, Simon J. ; Mohanty, Biswaranjan ; Roberts, Kade D. ; Yu, Heidi H. ; Scanlon, Martin J. ; Nation, Roger L. ; Velkov, Tony ; Li, Jian ; Thompson, Philp E. / The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity. In: Organic and Biomolecular Chemistry. 2017 ; Vol. 15, No. 34. pp. 7173-7180.

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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.",

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.}",

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language = "English",

volume = "15",

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journal = "Organic and Biomolecular Chemistry",

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The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity. / Mountford, Simon J.; Mohanty, Biswaranjan; Roberts, Kade D.; Yu, Heidi H.; Scanlon, Martin J.; Nation, Roger L.; Velkov, Tony; Li, Jian; Thompson, Philp E.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 34, 2017, p. 7173-7180.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

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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DO - 10.1039/c7ob01493g

M3 - Article

AN - SCOPUS:85028649518

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SP - 7173

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

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

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Polymyxin-like lipopeptide antibiotics of the future

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

Abstract

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Polymyxin-like lipopeptide antibiotics of the future

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