2- fluorobenzoate metabolism

Horvath RS, P Flathman (1976) Co-metabolism of fluorobenzoates by natural microbial populations. Appl Environ Microbiol 31 889-891. 

A two-component 2-halobenzoate 1,2-dioxygenase has been purified from Pseudomonas cepacia strain 2CBS that is able to metabolize 2-fluorobenzoate, 2-chlorobenzoate, 2-bromobenzoate, and 2-iodobenzoate to catechol by concomitant decarboxylation and loss of halide (Fetzner et al. 1992). The inducible 2-halobenzoate 1,2-dioxygenase consisted of... 

The metabolism of fluorobenzoates has been examined over many years. Early studies using Nocardia erythropoUs (Cain et al. 1968) and Pseudomonas fluorescens (Hughes 1965) showed that although the rates of whole-cell oxidation of fluorobenzoates were less than for benzoate, they were comparable to, and greater than for, the chlorinated analogs. As for their chlorinated analogs, both dioxygenation and hydrolytic pathways may be involved, and studies have revealed that the different pathways depended on the positions of the fluorine substituents. 

A mutant strain of Alcaligenes eutrophus was used (Reiner and Hegeman 1971) to demonstrate that the initial step in the metabolism of 4-fluorobenzoate involves 1 2 dioxygenation to 4-fluoro-1,2-dihydrodihydroxybenzene-l-carboxylate. 4-Fluorobenzoate may be used for growth by several bacteria, and metabolites produced by a strain of Pseudomonas sp., which was also able to degrade... 

Harper DB, ER Blakley (1971c) The metabolism of 7>-fluorobenzoic acid by a Pseudomonas sp. Can J Microbiol 17 1015-1023. 

Milne GWA, P Goldman, JL Holzman (1968) The metabolism of 2-fluorobenzoic acid. J Biol Chem 243 5374-5376. 

Elimination of fluoride from 2-fluorobenzoate may take place concomitantly with dioxygenation and carboxylation (Engesser et al. 1980) (Figure 6.125a) (Section 4.4.2), and in the metabolism of 2,5-difluorobenzoate that is metabolized via 4-fluorocatechol (Cass et al. 1987). 

Cavalieri, E.L., E.G. Rogan, P. Cremonesi, and P.D. Devanesan (1988). Radical cations as precursors in the metabolic formation of quinones from benzo[a]pyrene and 6-fluorobenzo[a]pyrene. Fluoro substitution as a probe for one-electron oxidation in aromatic substrates. Biochem. Pharmacol. 37, 2173-2182. 

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