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. 1968 Jan;106(1):211–227. doi: 10.1042/bj1060211

The utilization of some halogenated aromatic acids by Nocardia. Oxidation and metabolism

R B Cain 1, E Karen Tranter 1, Josephine A Darrah 1
PMCID: PMC1198488  PMID: 5721459

Abstract

1. Halogen analogues of p-nitrobenzoate and benzoate were oxidized by washed cells of Nocardia erythropolis. 2. The oxidation of 2-fluoro-4-nitrobenzoate ceased at the level of acetate, and fluoroacetate was found in the incubation medium and particularly in hot-ethanolic extracts of the cells. 3. Several fluorine-containing intermediates were detected and 2-fluoroprotocatechuate was identified as one of them. 4. The nitro group was also reduced by the organism, as evidenced by the formation of 4-amino-2-fluorobenzoate. 5. Extracts of N. erythropolis activated fluoroacetate and condensed the resulting fluoroacetyl-CoA with oxaloacetate to form fluorocitrate. This product was a very powerful inhibitor of citrate metabolism by guinea-pig kidney homogenates and of the aconitase also present in the bacterial extracts. The inhibitions effected by synthetic fluorocitrate and the natural product were comparable. 6. 2-Fluoro-4-nitrobenzoate had negligible mammalian toxicity. 7. The isolation of fluoroacetate as a product of 2-fluoro-4-nitrobenzoate oxidation implies that the aromatic ring in this bacterium must be degraded via a γ-carboxymuconolactone; fluoroacetate cannot arise by metabolism through the isomeric β-carboxymuconolactone.

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Selected References

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