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. 1986 Aug;52(2):334–339. doi: 10.1128/aem.52.2.334-339.1986

Influence of para-substituents on the oxidative metabolism of o-nitrophenols by Pseudomonas putida B2.

J Zeyer, H P Kocher, K N Timmis
PMCID: PMC203526  PMID: 3752997

Abstract

Pseudomonas putida B2 is able to grow on o-nitrophenol (ONP) as the sole source of carbon and nitrogen. ONP was converted by a nitrophenol oxygenase to nitrite and catechol. Catechol was then attacked by a catechol 1,2-dioxygenase and further degraded through an ortho-cleavage pathway. ONP derivatives which were para-substituted with a methyl-, chloro-, carboxy-, formyl- or nitro-group failed to support growth of strain B2. Relevant catabolic enzymes were characterized to analyze why these derivatives were not mineralized. Nitrophenol oxygenase of strain B2 is a soluble, NADPH-dependent enzyme that is stimulated by magnesium, manganese, and calcium ions. It is active toward ONP, 4-methyl-, 4-chloro-, and to a lesser extent, 4-formyl-ONP but not toward 4-carboxy- or 4-nitro-ONP. In addition, 4-formyl-, 4-carboxy-, and 4-nitro-ONP failed to induce the formation of nitrophenol oxygenase. Catechol 1,2-dioxygenase of strain B2 is active toward catechol and 4-methyl-catechol but only poorly active toward chlorinated catechols. 4-Methyl-catechol is likely to be degraded to methyl-lactones, which are often dead-end metabolites in bacteria. Thus, of the compounds tested, only unsubstituted ONP acts as an inducer and substrate for all of the enzymes of a productive catabolic pathway.

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Selected References

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  1. Braun K., Gibson D. T. Anaerobic degradation of 2-aminobenzoate (anthranilic acid) by denitrifying bacteria. Appl Environ Microbiol. 1984 Jul;48(1):102–107. doi: 10.1128/aem.48.1.102-107.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. CARTWRIGHT N. J., CAIN R. B. Bacterial degradation of the nitrobenzoic acids. Biochem J. 1959 Feb;71(2):248–261. doi: 10.1042/bj0710248. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Corbett M. D., Corbett B. R. Metabolism of 4-Chloronitrobenzene by the Yeast Rhodosporidium sp. Appl Environ Microbiol. 1981 Apr;41(4):942–949. doi: 10.1128/aem.41.4.942-949.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of catechol. Biochem J. 1978 Jul 15;174(1):85–94. doi: 10.1042/bj1740085. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. GERMANIER R., WUHRMANN K. UBER DEN AEROBEN MIKROBIELLEN ABBAU AROMATISCHER NITROVERBINDUNGEN. Pathol Microbiol (Basel) 1963;26:569–578. [PubMed] [Google Scholar]
  6. Hallas L. E., Alexander M. Microbial transformation of nitroaromatic compounds in sewage effluent. Appl Environ Microbiol. 1983 Apr;45(4):1234–1241. doi: 10.1128/aem.45.4.1234-1241.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Hegeman G. D. Synthesis of the enzymes of the mandelate pathway by Pseudomonas putida. I. Synthesis of enzymes by the wild type. J Bacteriol. 1966 Mar;91(3):1140–1154. doi: 10.1128/jb.91.3.1140-1154.1966. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Kido T., Hashizume K., Soda K. Purification and properties of nitroalkane oxidase from Fusarium oxysporum. J Bacteriol. 1978 Jan;133(1):53–58. doi: 10.1128/jb.133.1.53-58.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Kinouchi T., Ohnishi Y. Purification and characterization of 1-nitropyrene nitroreductases from Bacteroides fragilis. Appl Environ Microbiol. 1983 Sep;46(3):596–604. doi: 10.1128/aem.46.3.596-604.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Knackmuss H. J. Xenobiotic degradation in industrial sewage: haloaromatics as target substrates. Biochem Soc Symp. 1983;48:173–190. [PubMed] [Google Scholar]
  11. McCormick N. G., Feeherry F. E., Levinson H. S. Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. Appl Environ Microbiol. 1976 Jun;31(6):949–958. doi: 10.1128/aem.31.6.949-958.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Parris G. E. Environmental and metabolic transformations of primary aromatic amines and related compounds. Residue Rev. 1980;76:1–30. doi: 10.1007/978-1-4612-6107-0_1. [DOI] [PubMed] [Google Scholar]
  13. Powlowski J. B., Dagley S. beta-Ketoadipate pathway in Trichosporon cutaneum modified for methyl-substituted metabolites. J Bacteriol. 1985 Sep;163(3):1126–1135. doi: 10.1128/jb.163.3.1126-1135.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Reineke W., Knackmuss H. J. Chemical structure and biodegradability of halogenate aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim Biophys Acta. 1978 Sep 6;542(3):412–423. doi: 10.1016/0304-4165(78)90372-0. [DOI] [PubMed] [Google Scholar]
  15. Saarikoski J., Viluksela M. Relation between physicochemical properties of phenols and their toxicity and accumulation in fish. Ecotoxicol Environ Saf. 1982 Dec;6(6):501–512. doi: 10.1016/0147-6513(82)90032-x. [DOI] [PubMed] [Google Scholar]
  16. Spain J. C., Van Veld P. A. Adaptation of natural microbial communities to degradation of xenobiotic compounds: effects of concentration, exposure time, inoculum, and chemical structure. Appl Environ Microbiol. 1983 Feb;45(2):428–435. doi: 10.1128/aem.45.2.428-435.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Spain J. C., Wyss O., Gibson D. T. Enzymatic oxidation of p-nitrophenol. Biochem Biophys Res Commun. 1979 May 28;88(2):634–641. doi: 10.1016/0006-291x(79)92095-3. [DOI] [PubMed] [Google Scholar]
  18. Sylvestre M., Massé R., Messier F., Fauteux J., Bisaillon J. G., Beaudet R. Bacterial nitration of 4-chlorobiphenyl. Appl Environ Microbiol. 1982 Oct;44(4):871–877. doi: 10.1128/aem.44.4.871-877.1982. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. VILLANUEVA J. R. THE PURIFICATION OF A NITRO-REDUCTASE OF NOCARDIA V. J Biol Chem. 1964 Mar;239:773–776. [PubMed] [Google Scholar]
  20. Zeyer J., Wasserfallen A., Timmis K. N. Microbial mineralization of ring-substituted anilines through an ortho-cleavage pathway. Appl Environ Microbiol. 1985 Aug;50(2):447–453. doi: 10.1128/aem.50.2.447-453.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]

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