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. 1992 Aug;58(8):2501–2504. doi: 10.1128/aem.58.8.2501-2504.1992

Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepacia MB2 through the meta fission pathway.

F K Higson 1, D D Focht 1
PMCID: PMC195811  PMID: 1381172

Abstract

Pseudomonas cepacia MB2 grew on 3-chloro-2-methylbenzoate as a sole carbon source by metabolism through the meta fission pathway with the subsequent liberation of chloride. meta pyrocatechase activity in cell extracts was induced strongly by 3-chloro-2-methylbenzoate, but not by nongrowth analogs 4- or 5-chloro-2-methylbenzoate. Although rapid turnover of metabolites precluded direct identification, a mutant strain MB2-G5 lacking meta pyrocatechase activity produced 4-chloro-3-methylcatechol when incubated with 3-chloro-2-methylbenzoate. The catecholic product, confirmed by nuclear magnetic resonance and mass spectral analyses, produced a transient meta fission product (lambda max = 391 nm) from cell extracts of the wild-type MB2 strain. Further confirmation of meta pyrocatechase activity was noted by conversion of 4-chlorocatechol to 2-hydroxy-5-chloromuconic semialdehyde, which was not further metabolized. In contrast to 3-chlorocatechol, which was not metabolized and is known to generate suicidal products, 4-chlorocatechols do not generate acyl halides. Thus, further metabolism of the ring fission products is governed in strain MB2 by their suitability as substrates for the hydrolase.

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Selected References

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  1. Bartels I., Knackmuss H. J., Reineke W. Suicide Inactivation of Catechol 2,3-Dioxygenase from Pseudomonas putida mt-2 by 3-Halocatechols. Appl Environ Microbiol. 1984 Mar;47(3):500–505. doi: 10.1128/aem.47.3.500-505.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. DAGLEY S., CHAPMAN P. J., GIBSON D. T., WOOD J. M. DEGRADATION OF THE BENZENE NUCLEUS BY BACTERIA. Nature. 1964 May 23;202:775–778. doi: 10.1038/202775a0. [DOI] [PubMed] [Google Scholar]
  3. 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]
  4. Gaunt J. K., Evans W. C. Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Ring-fission, lactonizing and delactonizing enzymes. Biochem J. 1971 May;122(4):533–542. doi: 10.1042/bj1220533. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Gibson D. T., Koch J. R., Schuld C. L., Kallio R. E. Oxidative degradation of aromatic hydrocarbons by microorganisms. II. Metabolism of halogenated aromatic hydrocarbons. Biochemistry. 1968 Nov;7(11):3795–3802. doi: 10.1021/bi00851a003. [DOI] [PubMed] [Google Scholar]
  6. Haigler B. E., Spain J. C. Degradation of p-chlorotoluene by a mutant of Pseudomonas sp. strain JS6. Appl Environ Microbiol. 1989 Feb;55(2):372–379. doi: 10.1128/aem.55.2.372-379.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Hartmann J., Reineke W., Knackmuss H. J. Metabolism of 3-chloro-, 4-chloro-, and 3,5-dichlorobenzoate by a pseudomonad. Appl Environ Microbiol. 1979 Mar;37(3):421–428. doi: 10.1128/aem.37.3.421-428.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Higson F. K., Focht D. D. Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2. Appl Environ Microbiol. 1992 Jan;58(1):194–200. doi: 10.1128/aem.58.1.194-200.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Reineke W., Knackmuss H. J. Microbial degradation of haloaromatics. Annu Rev Microbiol. 1988;42:263–287. doi: 10.1146/annurev.mi.42.100188.001403. [DOI] [PubMed] [Google Scholar]
  10. Reineke W., Knackmuss H. J. Microbial metabolism of haloaromatics: isolation and properties of a chlorobenzene-degrading bacterium. Appl Environ Microbiol. 1984 Feb;47(2):395–402. doi: 10.1128/aem.47.2.395-402.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Spain J. C., Nishino S. F. Degradation of 1,4-dichlorobenzene by a Pseudomonas sp. Appl Environ Microbiol. 1987 May;53(5):1010–1019. doi: 10.1128/aem.53.5.1010-1019.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Vandenbergh P. A., Olsen R. H., Colaruotolo J. F. Isolation and genetic characterization of bacteria that degrade chloroaromatic compounds. Appl Environ Microbiol. 1981 Oct;42(4):737–739. doi: 10.1128/aem.42.4.737-739.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Whited G. M., McCombie W. R., Kwart L. D., Gibson D. T. Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid. J Bacteriol. 1986 Jun;166(3):1028–1039. doi: 10.1128/jb.166.3.1028-1039.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]

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