The utilization of some halogenated aromatic acids by Nocardia. Oxidation and metabolism.
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 gamma-carboxymuconolactone; fluoroacetate cannot arise by metabolism through the isomeric beta-carboxymuconolactone.
D000085:Acetates / Q000378:metabolism; D062365:Aminobenzoates / Q000378:metabolism; D000818:Animals; D001565:Benzoates / Q000378:metabolism* / Q000633:toxicity; D002396:Catechols / Q000378:metabolism; D002474:Cell-Free System; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002854:Chromatography, Paper; D002951:Citrates / Q000378:metabolism / Q000494:pharmacology; D003065:Coenzyme A / Q000378:metabolism; D005461:Fluorine / Q000378:metabolism* / Q000633:toxicity; D005463:Fluoroacetates / Q000378:metabolism; D006168:Guinea Pigs; D006836:Hydro-Lyases / Q000037:antagonists & inhibitors; D007668:Kidney / Q000378:metabolism; D007783:Lactones / Q000378:metabolism; D008190:Lyases / Q000378:metabolism; D008954:Models, Biological; D009578:Nitrobenzenes / Q000378:metabolism* / Q000633:toxicity; D009615:Nocardia / Q000378:metabolism*; D010071:Oxaloacetates / Q000378:metabolism; D010101:Oxygen Consumption; D013053:Spectrophotometry
D000085:Acetates; D062365:Aminobenzoates; D001565:Benzoates; D002396:Catechols; D002951:Citrates; D005463:Fluoroacetates; D007783:Lactones; D009578:Nitrobenzenes; D010071:Oxaloacetates; D005461:Fluorine; D008190:Lyases; D006836:Hydro-Lyases; D003065:Coenzyme A