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

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.

journal_name

Chemosphere

journal_title

Chemosphere

authors

Murphy CD,Schaffrath C,O'Hagan D

doi

10.1016/S0045-6535(03)00191-7

subject

Has Abstract

pub_date

2003-07-01 00:00:00

pages

455-61

issue

2

eissn

0045-6535

issn

1879-1298

pii

S0045-6535(03)00191-7

journal_volume

52

pub_type

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