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. 1982 Oct;44(4):871–877. doi: 10.1128/aem.44.4.871-877.1982

Bacterial Nitration of 4-Chlorobiphenyl

Michel Sylvestre 1, Robert Massé 1, François Messier 1, Johanne Fauteux 1, Jean-Guy Bisaillon 1, Réjean Beaudet 1
PMCID: PMC242111  PMID: 16346111

Abstract

In the course of a study dealing with the biodegradation of 4-chlorobiphenyl by strain B-206, we noticed that the gram-negative bacterium accumulated different metabolic intermediates depending on the nitrogen source of the medium. Hence, in the presence of nitrate, strain B-206 produced four compounds which were identified as 2- and 4-hydroxy-4′-chlorobiphenyl and 2- and 4-hydroxy-mononitro-4′-chlorobiphenyl. The accumulation of these compounds in the culture medium indicated the presence of a monooxygenase in strain B-206 leading to the production of arene oxide intermediates. The possible transformation of 4-chlorobiphenyl to an arene oxide by this bacterial strain is a matter of concern because of the high reactivity of these arene oxides with biological material.

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Selected References

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  1. Alexander M. Biodegradation of chemicals of environmental concern. Science. 1981 Jan 9;211(4478):132–138. doi: 10.1126/science.7444456. [DOI] [PubMed] [Google Scholar]
  2. Aranha H. G., Brown L. R. Effect of nitrogen source on end products of naphthalene degradation. Appl Environ Microbiol. 1981 Jul;42(1):74–78. doi: 10.1128/aem.42.1.74-78.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Chatterjee D. K., Kellogg S. T., Hamada S., Chakrabarty A. M. Plasmid specifying total degradation of 3-chlorobenzoate by a modified ortho pathway. J Bacteriol. 1981 May;146(2):639–646. doi: 10.1128/jb.146.2.639-646.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Daly J. W., Jerina D. M., Witkop B. Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia. 1972 Oct 15;28(10):1129–1149. doi: 10.1007/BF01946135. [DOI] [PubMed] [Google Scholar]
  5. Dorn E., Hellwig M., Reineke W., Knackmuss H. J. Isolation and characterization of a 3-chlorobenzoate degrading pseudomonad. Arch Microbiol. 1974;99(1):61–70. doi: 10.1007/BF00696222. [DOI] [PubMed] [Google Scholar]
  6. Focht D. D., Alexander M. Aerobic cometabolism of DDT analogues by Hydrogenomonas sp. J Agric Food Chem. 1971 Jan-Feb;19(1):20–22. doi: 10.1021/jf60173a042. [DOI] [PubMed] [Google Scholar]
  7. Furukawa K., Matsumura F. Microbial metabolism of polychlorinated biphenyls. Studies on the relative degradability of polychlorinated biphenyl components by Alkaligenes sp. J Agric Food Chem. 1976 Mar-Apr;24(2):251–256. doi: 10.1021/jf60204a002. [DOI] [PubMed] [Google Scholar]
  8. Gardner A. M., Chen J. T., Roach J. A., Ragelis E. P. Polychlorinated biphenyls: hydroxylated urinary metabolites of 2,5,2',5'-tetrachlorobiphenyl identified in rabbits. Biochem Biophys Res Commun. 1973 Dec 19;55(4):1377–1384. doi: 10.1016/s0006-291x(73)80046-4. [DOI] [PubMed] [Google Scholar]
  9. Gaunt J. K., Evans W. C. Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Preliminary evidence for the metabolic pathway. Biochem J. 1971 May;122(4):519–526. doi: 10.1042/bj1220519. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Gibson D. T., Roberts R. L., Wells M. C., Kobal V. M. Oxidation of biphenyl by a Beijerinckia species. Biochem Biophys Res Commun. 1973 Jan 23;50(2):211–219. doi: 10.1016/0006-291x(73)90828-0. [DOI] [PubMed] [Google Scholar]
  11. Jerina D. M., Daly J. W., Jeffrey A. M., Gibson D. T. Cis-1,2-dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch Biochem Biophys. 1971 Jan;142(1):394–396. doi: 10.1016/0003-9861(71)90298-0. [DOI] [PubMed] [Google Scholar]
  12. McCann J., Choi E., Yamasaki E., Ames B. N. Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals. Proc Natl Acad Sci U S A. 1975 Dec;72(12):5135–5139. doi: 10.1073/pnas.72.12.5135. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Mires M. H., Alexander C. H. The prophylactic treatment tuberculosis. Del Med J. 1972 Jul;44(7):187–190. [PubMed] [Google Scholar]
  14. Oswald E. O., Albro P. W., McKinney J. D. Utilization of gas-liquid chromatography coupled with chemical ionization and electron impact mass spectrometry for the investigation of potentially hazardous environmental agents and their metabolites. J Chromatogr. 1974 Sep 25;98(2):363–448. doi: 10.1016/s0021-9673(00)92078-8. [DOI] [PubMed] [Google Scholar]
  15. Safe S., Hutzinger O., Jones D. The mechanism of chlorobiphenyl metabolism. J Agric Food Chem. 1975 Sep-Oct;23(5):851–853. doi: 10.1021/jf60201a039. [DOI] [PubMed] [Google Scholar]
  16. Suzuki T. Metabolism of pentachlorophenol by a soil microbe. J Environ Sci Health B. 1977;12(2):113–127. doi: 10.1080/03601237709372057. [DOI] [PubMed] [Google Scholar]
  17. Sylvestre M. Isolation Method for Bacterial Isolates Capable of Growth on p-Chlorobiphenyl. Appl Environ Microbiol. 1980 Jun;39(6):1223–1224. doi: 10.1128/aem.39.6.1223-1224.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Wyndham C., Devenish J., Safe S. The in vitro metabolism, macromolecular binding and bacterial mutagenicity of 4-chloribiphenyl, a model PCB substrate. Res Commun Chem Pathol Pharmacol. 1976 Nov;15(3):563–570. [PubMed] [Google Scholar]
  19. Zamir L. O., Hufford K. D. Precursor recognition by kinetic pulse-labeling in a toxigenic aflatoxin B1-producing strain of Aspergillus. Appl Environ Microbiol. 1981 Jul;42(1):168–173. doi: 10.1128/aem.42.1.168-173.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]

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