Organofluorine Chemistry - Biosynthesis of Organofluorine Compounds

Biosynthesis of Organofluorine Compounds

In contrast to the many naturally-occurring organic compounds containing the heavier halides, chloride, bromide, and iodide, only a handful of biologically synthesized carbon-fluorine bonds are known. The most common natural organofluorine species is fluoroacetate, a toxin found in a few species of plants. Others include fluorooleic acid, fluoroacetone, nucleocidin (4’-fuoro-5’-O-sulphamoyladenosine), fluorothreonine, and 2-fluorocitrate. Several of these species are probably biosynthesized from fluoroacetaldehyde. The enzyme fluorinase catalyzed the synthesis of 5'-fluoro-5-deoxyadenosine (see scheme to right).

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