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

33 Citations (Scopus)

682 Downloads (Pure)

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

UN SDGs

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

SDG 14 Life Below Water

Research Groups and Themes

BCS and TECS CDTs
Bristol BioDesign Institute
Organic & Biological

Keywords

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

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. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
BIOSYNTHESIS OF POLYKETIDE ANTIBIOTIC MUPIROCIN BY PSEUDOMONAS FLUORESCENS
Simpson, T. J. (Principal Investigator)
1/12/07 → 1/05/11
Project: Research
PROBING DRUG RECEPTOR BINDING SITES DRIVEN BY SOLID STATE NMR-AN INTERDISCIPLINARY APPROACH
Willis, C. L. (Principal Investigator)
1/11/06 → 1/05/12
Project: Research

Dr John Crosby
- John.Crosbybristol.acuk
- School of Chemistry - Associate Professor
Person: Academic
Professor Chris L Willis
- Chris.Willisbristol.acuk
- School of Chemistry - Professor of Organic Chemistry
Person: Academic

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

KW - ANTIBIOTICS

KW - MUPIROCIN

KW - XENORHABDUS

KW - ANTIMICROBIAL ACTIVITY

KW - MARINE BACTERIUM

KW - HOLOMYCIN

KW - FLUORESCENS

KW - GENE-CLUSTER

KW - PSEUDOMONIC-ACID-A

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

UN SDGs

Research Groups and Themes

Keywords

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