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. 1991 Nov;57(11):3361–3366. doi: 10.1128/aem.57.11.3361-3366.1991

Metabolism of and inhibition by chlorobenzoates in Pseudomonas putida P111.

B S Hernandez 1, F K Higson 1, R Kondrat 1, D D Focht 1
PMCID: PMC183972  PMID: 1781694

Abstract

Pseudomonas putida P111 was isolated by enrichment culture on 2,5-dichlorobenzoate and was also able to grow on 2-chloro-, 3-chloro-, 4-chloro-, 2,3-dichloro-, 2,4-dichloro-, and 2,3,5-trichlorobenzoates. However, 3,5-dichlorobenzoate completely inhibited growth of P111 on all ortho-substituted benzoates that were tested. When 3,5-dichlorobenzoate was added as a cosubstrate with either 3- or 4-chlorobenzoate, cell yields and chloride release were greater than those observed from growth on either monochlorobenzoate alone. Moreover, resting cells of P111 grown on 4-chlorobenzoate released chloride from 3,5-dichlorobenzoate and produced no identifiable intermediate. In contrast, resting cells grown on 2,5-dichlorobenzoate metabolized 3,5-dichlorobenzoate without release of chloride and accumulated a degradation product, which was identified as 1-carboxy-1,2-dihydroxy-3,5-dichlorocyclohexadiene on the basis of gas chromatography-mass spectrometry confirmation of its two acid-hydrolyzed products, 3,5- and 2,4-dichlorophenol. Since 3,5-dichlorocatechol was rapidly metabolized by cells grown on 2,5-dichlorobenzoate, it is apparent that 1-carboxy-1,2-dihydroxy-3,5-dichlorocyclohexadiene is not further metabolized by these cells. Moreover, induction of a functional dihyrodiol dehydrogenase would not be required for growth of P111 on other ortho-chlorobenzoates since the corresponding chlorodihydrodiols produced from a 1,2-dioxygenase attack would spontaneously decompose to the corresponding catechols. In contrast, growth on 3-chloro-, 4-chloro-, or 3,5-dichlorobenzoate requires a functional dihydrodiol dehydrogenase, yet only the two monochlorobenzoates appear to induce for it.

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Selected References

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  1. Adriaens P., Focht D. D. Cometabolism of 3,4-dichlorobenzoate by Acinetobacter sp. strain 4-CB1. Appl Environ Microbiol. 1991 Jan;57(1):173–179. doi: 10.1128/aem.57.1.173-179.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Adriaens P., Kohler H. P., Kohler-Staub D., Focht D. D. Bacterial dehalogenation of chlorobenzoates and coculture biodegradation of 4,4'-dichlorobiphenyl. Appl Environ Microbiol. 1989 Apr;55(4):887–892. doi: 10.1128/aem.55.4.887-892.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol 1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad. Biochem J. 1978 Jul 15;174(1):73–84. doi: 10.1042/bj1740073. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Fetzner S., Müller R., Lingens F. A novel metabolite in the microbial degradation of 2-chlorobenzoate. Biochem Biophys Res Commun. 1989 Jun 15;161(2):700–705. doi: 10.1016/0006-291x(89)92656-9. [DOI] [PubMed] [Google Scholar]
  5. Focht D. D., Shelton D. Growth kinetics of Pseudomonas alcaligenes C-0 relative to inoculation and 3-chlorobenzoate metabolism in soil. Appl Environ Microbiol. 1987 Aug;53(8):1846–1849. doi: 10.1128/aem.53.8.1846-1849.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Gibson D. T., Mahadevan V., Davey J. F. Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring. J Bacteriol. 1974 Sep;119(3):930–936. doi: 10.1128/jb.119.3.930-936.1974. [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. Hickey W. J., Focht D. D. Degradation of mono-, di-, and trihalogenated benzoic acids by Pseudomonas aeruginosa JB2. Appl Environ Microbiol. 1990 Dec;56(12):3842–3850. doi: 10.1128/aem.56.12.3842-3850.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Higson F. K., Focht D. D. Bacterial metabolism of hydroxylated biphenyls. Appl Environ Microbiol. 1989 Apr;55(4):946–952. doi: 10.1128/aem.55.4.946-952.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Horvath R. S., Alexander M. Cometabolism of m-chlorobenzoate by an Arthrobacter. Appl Microbiol. 1970 Aug;20(2):254–258. doi: 10.1128/am.20.2.254-258.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  12. Marks T. S., Smith A. R., Quirk A. V. Degradation of 4-Chlorobenzoic Acid by Arthrobacter sp. Appl Environ Microbiol. 1984 Nov;48(5):1020–1025. doi: 10.1128/aem.48.5.1020-1025.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Marks T. S., Wait R., Smith A. R., Quirk A. V. The origin of the oxygen incorporated during the dehalogenation/hydroxylation of 4-chlorobenzoate by an Arthrobacter sp. Biochem Biophys Res Commun. 1984 Oct 30;124(2):669–674. doi: 10.1016/0006-291x(84)91607-3. [DOI] [PubMed] [Google Scholar]
  14. Miguez C. B., Greer C. W., Ingram J. M. Degradation of mono- and dichlorobenzoic acid isomers by two natural isolates of Alcaligenes denitrificans. Arch Microbiol. 1990;154(2):139–143. doi: 10.1007/BF00423323. [DOI] [PubMed] [Google Scholar]
  15. Müller R., Oltmanns R. H., Lingens F. Enzymatic dehalogenation of 4-chlorobenzoate by extracts from Arthrobacter sp. SU DSM 20407. Biol Chem Hoppe Seyler. 1988 Jul;369(7):567–571. doi: 10.1515/bchm3.1988.369.2.567. [DOI] [PubMed] [Google Scholar]
  16. Pertsova R. N., Kunc F., Golovleva L. A. Degradation of 3-chlorobenzoate in soil by pseudomonads carrying biodegradative plasmids. Folia Microbiol (Praha) 1984;29(3):242–247. doi: 10.1007/BF02877315. [DOI] [PubMed] [Google Scholar]
  17. Sylvestre M., Mailhiot K., Ahmad D., Massé R. Isolation and preliminary characterization of a 2-chlorobenzoate degrading Pseudomonas. Can J Microbiol. 1989 Apr;35(4):439–443. doi: 10.1139/m89-067. [DOI] [PubMed] [Google Scholar]

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