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 journalArticle (Academic Journal)

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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 languageEnglish
Pages (from-to)397-402
Number of pages6
JournalChemical Science
Volume5
Issue number1
Early online date1 Nov 2013
DOIs
Publication statusPublished - 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

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Cite this

Murphy, A. C., Gao, S-S., Han, L-C., Carobene, S., Fukuda, D., Song, Z., Hothersall, J., Cox, R. J., Crosby, J., Crump, M. P., Thomas, C. M., Willis, C. L., & Simpson, T. J. (2014). Biosynthesis of thiomarinol A and related metabolites of Pseudoalteromonas sp SANK 73390. Chemical Science, 5(1), 397-402. https://doi.org/10.1039/c3sc52281d