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; Christine L. Willis; Thomas J. Simpson; Christopher Thomas

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, Christine L. Willis^*, Thomas J. Simpson, Christopher Thomas

^*Corresponding author for this work

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

26 Citations (Scopus)

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
DOIs	https://doi.org/10.1039/c3sc52281d
Publication status	Published - Jan 2014

ASJC Scopus subject areas

Chemistry(all)

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

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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.",

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

year = "2014",

month = jan,

doi = "10.1039/c3sc52281d",

language = "English",

volume = "5",

pages = "397--402",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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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 - Willis, Christine L.

AU - Simpson, Thomas J.

AU - Thomas, Christopher

PY - 2014/1

Y1 - 2014/1

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.

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U2 - 10.1039/c3sc52281d

DO - 10.1039/c3sc52281d

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JO - Chemical Science

JF - Chemical Science

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

Abstract

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