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

Biochem J. 1968 Jan;106(1):211-27. doi: 10.1042/bj1060211.

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 gamma-carboxymuconolactone; fluoroacetate cannot arise by metabolism through the isomeric beta-carboxymuconolactone.

MeSH terms

  • Acetates / metabolism
  • Aminobenzoates / metabolism
  • Animals
  • Benzoates / metabolism*
  • Benzoates / toxicity
  • Catechols / metabolism
  • Cell-Free System
  • Chemical Phenomena
  • Chemistry
  • Chromatography, Gas
  • Chromatography, Paper
  • Citrates / metabolism
  • Citrates / pharmacology
  • Coenzyme A / metabolism
  • Fluorine / metabolism*
  • Fluorine / toxicity
  • Fluoroacetates / metabolism
  • Guinea Pigs
  • Hydro-Lyases / antagonists & inhibitors
  • Kidney / metabolism
  • Lactones / metabolism
  • Lyases / metabolism
  • Models, Biological
  • Nitrobenzenes / metabolism*
  • Nitrobenzenes / toxicity
  • Nocardia / metabolism*
  • Oxaloacetates / metabolism
  • Oxygen Consumption
  • Spectrophotometry

Substances

  • Acetates
  • Aminobenzoates
  • Benzoates
  • Catechols
  • Citrates
  • Fluoroacetates
  • Lactones
  • Nitrobenzenes
  • Oxaloacetates
  • Fluorine
  • Lyases
  • Hydro-Lyases
  • Coenzyme A