Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya

CD Murphy, C Schaffrath, David O'Hagan

Research output: Contribution to journalArticlepeer-review

77 Citations (Scopus)

Abstract

Organofluorine compounds are rare in Nature, with only a handful known to be produced by some species of plant and two microorganisms. Consequently, the mechanism of enzymatic carbon-fluorine bond formation is poorly understood. The bacterium Streptomyces cattleya biosynthesises fluoroacetate and 4-fluorothreonine as secondary metabolites and is a convenient system to study the biosynthesis and enzymology of fluorometabolite production. Using stable-isotope labelled precursors it has been shown that there is a common intermediate in the biosynthesis of the fluorometabolites, which has recently been identified as fluoroacetaldehyde. Studies with cell-free extracts of S. cattleya have identified two enzymes, an aldehyde dehydrogenase and a threonine transaldolase, that are involved in the biotransformation of fluoroacetaldehyde to fluoroacetate and 4-fluorothreonine. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)455-461
Number of pages7
JournalChemosphere
Volume52
Issue number2
DOIs
Publication statusPublished - Jul 2003

Keywords

  • biohalogenation
  • secondary metabolite
  • transaldolase
  • aldehyde dehydrogenase
  • SECONDARY METABOLITES
  • 4-CHLOROTHREONINE
  • ORGANICS
  • COMPLEX
  • ORIGIN

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