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

Chemosphere. 2003 Jul;52(2):455-61. doi: 10.1016/S0045-6535(03)00191-7.

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.

MeSH terms

  • Acetaldehyde / analogs & derivatives*
  • Acetaldehyde / metabolism
  • Aldehyde Dehydrogenase / isolation & purification
  • Aldehyde Dehydrogenase / metabolism
  • Biotransformation
  • Carbon Isotopes
  • Catalysis
  • Cell-Free System
  • Deuterium
  • Fluorine Radioisotopes
  • Fluoroacetates / metabolism*
  • Magnetic Resonance Spectroscopy / methods
  • Streptomyces / metabolism*
  • Threonine / analogs & derivatives*
  • Threonine / biosynthesis*
  • Threonine / metabolism
  • Transaldolase / isolation & purification
  • Transaldolase / metabolism

Substances

  • Carbon Isotopes
  • Fluorine Radioisotopes
  • Fluoroacetates
  • 4-fluorothreonine
  • fluoroacetaldehyde
  • Threonine
  • Deuterium
  • Aldehyde Dehydrogenase
  • Transaldolase
  • Acetaldehyde