Mupirocin F: structure elucidation, synthesis and rearrangements

RW Scott; AC Murphy; J Wu; J Hothersall; RJ Cox; TJ Simpson; Christopher Thomas; CL Willis

doi:10.1016/j.tet.2011.05.021

Mupirocin F: structure elucidation, synthesis and rearrangements

RW Scott, AC Murphy, J Wu, J Hothersall, RJ Cox, TJ Simpson, Christopher Thomas, CL Willis

Biosciences

Research output: Contribution to journal › Article

7 Citations (Scopus)

Abstract

The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5098-5106
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2011.05.021
Publication status	Published - 1 Jul 2011

Keywords

Rearrangements
Structure elucidation
Selective oxidation
Polyketide

Access to Document

10.1016/j.tet.2011.05.021

Biosynthesis of polyketide antibiotic mupirocin by Pseudomonas fluorescens
Thomas, C.
Biotechnology & Biological Sciences Research Council
1/06/07 → 30/01/11
Project: Research Councils
Biosynthesis of the Polyketide Antibiotic Mupirocin by Pseudomonas Fluorescens
Thomas, C. & Hothersall, J.
Biotechnology & Biological Sciences Research Council
14/05/04 → 13/05/07
Project: Research Councils

Cite this

@article{dcc0cb8837354957b0870d695a01091c,

title = "Mupirocin F: structure elucidation, synthesis and rearrangements",

abstract = "The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Rearrangements, Structure elucidation, Selective oxidation, Polyketide",

author = "RW Scott and AC Murphy and J Wu and J Hothersall and RJ Cox and TJ Simpson and Christopher Thomas and CL Willis",

year = "2011",

month = jul,

day = "1",

doi = "10.1016/j.tet.2011.05.021",

language = "English",

volume = "67",

pages = "5098--5106",

journal = "Tetrahedron",

publisher = "Elsevier",

number = "27-28",

}

TY - JOUR

T1 - Mupirocin F: structure elucidation, synthesis and rearrangements

AU - Scott, RW

AU - Murphy, AC

AU - Wu, J

AU - Hothersall, J

AU - Cox, RJ

AU - Simpson, TJ

AU - Thomas, Christopher

AU - Willis, CL

PY - 2011/7/1

Y1 - 2011/7/1

N2 - The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

AB - The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

KW - Rearrangements

KW - Structure elucidation

KW - Selective oxidation

KW - Polyketide

U2 - 10.1016/j.tet.2011.05.021

DO - 10.1016/j.tet.2011.05.021

M3 - Article

VL - 67

SP - 5098

EP - 5106

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

Mupirocin F: structure elucidation, synthesis and rearrangements

Abstract

Keywords

Access to Document

Fingerprint

Projects

Biosynthesis of polyketide antibiotic mupirocin by Pseudomonas fluorescens

Biosynthesis of the Polyketide Antibiotic Mupirocin by Pseudomonas Fluorescens

Cite this