Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya.
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.
Murphy
Cormac D
CD
School of Chemistry, Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife KY16 9ST, UK. cormac.d.murphy@ucd.ie
Schaffrath
Christoph
C
O'Hagan
David
D
D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000378:metabolism; D000444:Aldehyde Dehydrogenase / Q000302:isolation & purification / Q000378:metabolism; D001711:Biotransformation; D002247:Carbon Isotopes; D002384:Catalysis; D002474:Cell-Free System; D003903:Deuterium; D005462:Fluorine Radioisotopes; D005463:Fluoroacetates / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013302:Streptomyces / Q000378:metabolism*; D013912:Threonine / Q000031:analogs & derivatives* / Q000096:biosynthesis* / Q000378:metabolism; D014153:Transaldolase / Q000302:isolation & purification / Q000378:metabolism
D002247:Carbon Isotopes; D005462:Fluorine Radioisotopes; D005463:Fluoroacetates; C048271:4-fluorothreonine; C075898:fluoroacetaldehyde; D013912:Threonine; D003903:Deuterium; D000444:Aldehyde Dehydrogenase; D014153:Transaldolase; D000079:Acetaldehyde