Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390

Annabel C. Murphy; Shu-Shan Gao; Li-Chen Han; Simon Carobene; Daisuke Fukuda; Zhongshu Song; Joanne Hothersall; Russell J. Cox; John Crosby; Matthew P. Crump; Christopher M. Thomas; Christine L. Willis; Thomas J. Simpson

doi:10.1039/c3sc52281d

Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390

Annabel C. Murphy, Shu-Shan Gao, Li-Chen Han, Simon Carobene, Daisuke Fukuda, Zhongshu Song, Joanne Hothersall, Russell J. Cox, John Crosby, Matthew P. Crump, Christopher M. Thomas, Christine L. Willis^*, Thomas J. Simpson

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

The biosynthesis of the mixed PKS-FAS-NRPS hybrid antibiotic thiomarinol A was investigated using feeding studies to both wild type and mutant strains of the marine bacterium Pseudoalteromonas. Particularly interesting features of the pathway include assembly of the 8-hydroxyoctanoic acid side-chain via chain extension of a C₄-precursor (4-hydroxybutyrate), and construction of the pyrrothine unit from cysteine via (HolA-D, F-H) prior to intact incorporation into thiomarinol (catalysed by TmlU). A series of thiomarinol-related and other minor metabolites have been isolated from wild-type and mutant strains. The results of these investigations are rationalised in terms of the overall biosynthetic pathway.

Original language	English
Pages (from-to)	397-402
Number of pages	6
Journal	Chemical Science
Volume	5
Issue number	1
Early online date	1 Nov 2013
DOIs	https://doi.org/10.1039/c3sc52281d
Publication status	Published - 1 Jan 2014

Structured keywords

BCS and TECS CDTs

Keywords

PSEUDOMONIC-ACID-A
MARINE BACTERIUM
ANTIMICROBIAL ACTIVITY
GENE-CLUSTER
FLUORESCENS
ANTIBIOTICS
MUPIROCIN
XENORHABDUS
HOLOMYCIN
PATHWAY

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1039/c3sc52281d

Full-text PDF (final published version)
This is the final published version of the article (version of record). It first appeared online via Royal Society of Chemistry at http://dx.doi.org/10.1039/C3SC52281D. Please refer to any applicable terms of use of the publisher.
Final published version, 478 KBLicence: CC BY
Supplementary information PDF
This is the final published version of the article (version of record). It first appeared online via Royal Society of Chemistry at http://dx.doi.org/10.1039/C3SC52281D. Please refer to any applicable terms of use of the publisher.
Final published version, 1.29 MBLicence: CC BY

Handle.net

Persistent link

3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
BIOSYNTHESIS OF POLYKETIDE ANTIBIOTIC MUPIROCIN BY PSEUDOMONAS FLUORESCENS
Simpson, T. J.
1/12/07 → 1/05/11
Project: Research
PROBING DRUG RECEPTOR BINDING SITES DRIVEN BY SOLID STATE NMR-AN INTERDISCIPLINARY APPROACH
Willis, C. L.
1/11/06 → 1/05/12
Project: Research

Dr John Crosby
- John.Crosbybristol.acuk
- School of Chemistry - Associate Professor
- Biological and Archaeological Chemistry
Person: Academic , Member
Professor Chris L Willis
- Chris.Willisbristol.acuk
- Fundamental Bioscience
- Synthesis
- School of Chemistry - Professor of Organic Chemistry
- Catalysis
- Biological and Archaeological Chemistry
Person: Academic , Member

Cite this

@article{c157cd165f2e485ba604451940a3476b,

title = "Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390",

abstract = "The biosynthesis of the mixed PKS-FAS-NRPS hybrid antibiotic thiomarinol A was investigated using feeding studies to both wild type and mutant strains of the marine bacterium Pseudoalteromonas. Particularly interesting features of the pathway include assembly of the 8-hydroxyoctanoic acid side-chain via chain extension of a C4-precursor (4-hydroxybutyrate), and construction of the pyrrothine unit from cysteine via (HolA-D, F-H) prior to intact incorporation into thiomarinol (catalysed by TmlU). A series of thiomarinol-related and other minor metabolites have been isolated from wild-type and mutant strains. The results of these investigations are rationalised in terms of the overall biosynthetic pathway.",

keywords = "PSEUDOMONIC-ACID-A, MARINE BACTERIUM, ANTIMICROBIAL ACTIVITY, GENE-CLUSTER, FLUORESCENS, ANTIBIOTICS, MUPIROCIN, XENORHABDUS, HOLOMYCIN, PATHWAY",

author = "Murphy, {Annabel C.} and Shu-Shan Gao and Li-Chen Han and Simon Carobene and Daisuke Fukuda and Zhongshu Song and Joanne Hothersall and Cox, {Russell J.} and John Crosby and Crump, {Matthew P.} and Thomas, {Christopher M.} and Willis, {Christine L.} and Simpson, {Thomas J.}",

year = "2014",

month = jan,

day = "1",

doi = "10.1039/c3sc52281d",

language = "English",

volume = "5",

pages = "397--402",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390

AU - Murphy, Annabel C.

AU - Gao, Shu-Shan

AU - Han, Li-Chen

AU - Carobene, Simon

AU - Fukuda, Daisuke

AU - Song, Zhongshu

AU - Hothersall, Joanne

AU - Cox, Russell J.

AU - Crosby, John

AU - Crump, Matthew P.

AU - Thomas, Christopher M.

AU - Willis, Christine L.

AU - Simpson, Thomas J.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - The biosynthesis of the mixed PKS-FAS-NRPS hybrid antibiotic thiomarinol A was investigated using feeding studies to both wild type and mutant strains of the marine bacterium Pseudoalteromonas. Particularly interesting features of the pathway include assembly of the 8-hydroxyoctanoic acid side-chain via chain extension of a C4-precursor (4-hydroxybutyrate), and construction of the pyrrothine unit from cysteine via (HolA-D, F-H) prior to intact incorporation into thiomarinol (catalysed by TmlU). A series of thiomarinol-related and other minor metabolites have been isolated from wild-type and mutant strains. The results of these investigations are rationalised in terms of the overall biosynthetic pathway.

AB - The biosynthesis of the mixed PKS-FAS-NRPS hybrid antibiotic thiomarinol A was investigated using feeding studies to both wild type and mutant strains of the marine bacterium Pseudoalteromonas. Particularly interesting features of the pathway include assembly of the 8-hydroxyoctanoic acid side-chain via chain extension of a C4-precursor (4-hydroxybutyrate), and construction of the pyrrothine unit from cysteine via (HolA-D, F-H) prior to intact incorporation into thiomarinol (catalysed by TmlU). A series of thiomarinol-related and other minor metabolites have been isolated from wild-type and mutant strains. The results of these investigations are rationalised in terms of the overall biosynthetic pathway.

KW - PSEUDOMONIC-ACID-A

KW - MARINE BACTERIUM

KW - ANTIMICROBIAL ACTIVITY

KW - GENE-CLUSTER

KW - FLUORESCENS

KW - ANTIBIOTICS

KW - MUPIROCIN

KW - XENORHABDUS

KW - HOLOMYCIN

KW - PATHWAY

U2 - 10.1039/c3sc52281d

DO - 10.1039/c3sc52281d

M3 - Article (Academic Journal)

SN - 2041-6520

VL - 5

SP - 397

EP - 402

JO - Chemical Science

JF - Chemical Science

IS - 1

ER -

Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390

Abstract

Structured keywords

Keywords

UN SDGs

Access to Document

Handle.net

Fingerprint

Projects

3-month Core Capability for Chemistry Research

BIOSYNTHESIS OF POLYKETIDE ANTIBIOTIC MUPIROCIN BY PSEUDOMONAS FLUORESCENS

PROBING DRUG RECEPTOR BINDING SITES DRIVEN BY SOLID STATE NMR-AN INTERDISCIPLINARY APPROACH

Profiles

Dr John Crosby

Professor Chris L Willis

Cite this