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

Murphy, Cormac D., Schaffrath, Christoph, O’Hagan, David·2003·Chemosphere
DOI 10.1016/s0045-6535(03)00191-7
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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.

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  • Fluoroacetate is a natural organofluoride compound that is toxic to mammals and produced by actinomycetes, such as Streptomyces cattleya, and acts as a defense molecule in some plants.

    “Fluoroacetate is a natural organofluoride compound that is toxic to mammals and produced by actinomycetes, such as Streptomyces cattleya (57), and acts as a defense molecule in some plants (58, 59).”

    From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [57]

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Research works printed but not linked: 36

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Metadata

Authors
Murphy, C. D., Schaffrath, C., & O’Hagan, D.
Venue
Chemosphere
Publisher
Elsevier BV
Published
2003-07
Volume
52
Issue
2
Pages
455-461
ISSN
0045-6535
DOI
10.1016/s0045-6535(03)00191-7
Cited by
87
References
0
Language
en
Licence
www.elsevier.com/tdm/userlicense/1.0/ (tdm)

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