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. 1995 Feb;61(2):443–447. doi: 10.1128/aem.61.2.443-447.1995

A meta cleavage pathway for 4-chlorobenzoate, an intermediate in the metabolism of 4-chlorobiphenyl by Pseudomonas cepacia P166.

J J Arensdorf 1, D D Focht 1
PMCID: PMC167302  PMID: 7574580

Abstract

Bacterial degradation of biphenyl and polychlorinated biphenyls proceeds by a well-studied pathway which produces benzoate and 2-hydroxypent-2,4-dienoate (or, in the case of polychlorinated biphenyls, the chlorinated derivatives of these compounds). Pseudomonas cepacia P166 utilizes 4-chlorobiphenyl for growth and produces 4-chlorobenzoate as a central intermediate. In this study we found that strain P166 further transforms 4-chlorobenzoate to 4-chlorocatechol, which is mineralized by a meta cleavage pathway. Key metabolites which we identified include the meta cleavage product (5-chloro-2-hydroxymuconic semialdehyde), 5-chloro-2-hydroxymuconate, 5-chloro-2-oxopent-4-enoate, 5-chloro-4-hydroxy-2-oxopentanoate, and chloroacetate. Chloroacetate accumulated transiently, and slow but stoichiometric dehalogenation was observed.

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Selected References

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  1. Adams R. H., Huang C. M., Higson F. K., Brenner V., Focht D. D. Construction of a 3-chlorobiphenyl-utilizing recombinant from an intergeneric mating. Appl Environ Microbiol. 1992 Feb;58(2):647–654. doi: 10.1128/aem.58.2.647-654.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Ahmed M., Focht D. D. Degradation of polychlorinated biphenyls by two species of Achromobacter. Can J Microbiol. 1973 Jan;19(1):47–52. doi: 10.1139/m73-007. [DOI] [PubMed] [Google Scholar]
  3. Arensdorf J. J., Focht D. D. Formation of chlorocatechol meta cleavage products by a pseudomonad during metabolism of monochlorobiphenyls. Appl Environ Microbiol. 1994 Aug;60(8):2884–2889. doi: 10.1128/aem.60.8.2884-2889.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Assinder S. J., Williams P. A. The TOL plasmids: determinants of the catabolism of toluene and the xylenes. Adv Microb Physiol. 1990;31:1–69. doi: 10.1016/s0065-2911(08)60119-8. [DOI] [PubMed] [Google Scholar]
  5. Barton M. R., Crawford R. L. Novel biotransformations of 4-chlorobiphenyl by a Pseudomonas sp. Appl Environ Microbiol. 1988 Feb;54(2):594–595. doi: 10.1128/aem.54.2.594-595.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Burlage R. S., Hooper S. W., Sayler G. S. The TOL (pWW0) catabolic plasmid. Appl Environ Microbiol. 1989 Jun;55(6):1323–1328. doi: 10.1128/aem.55.6.1323-1328.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Catelani D., Sorlini C., Treccani V. The metabolism of biphenyl by Pseudomonas putida. Experientia. 1971 Oct 15;27(10):1173–1174. doi: 10.1007/BF02286908. [DOI] [PubMed] [Google Scholar]
  8. Cerniglia C. E. Microbial metabolism of polycyclic aromatic hydrocarbons. Adv Appl Microbiol. 1984;30:31–71. doi: 10.1016/s0065-2164(08)70052-2. [DOI] [PubMed] [Google Scholar]
  9. Furukawa K., Miyazaki T. Cloning of a gene cluster encoding biphenyl and chlorobiphenyl degradation in Pseudomonas pseudoalcaligenes. J Bacteriol. 1986 May;166(2):392–398. doi: 10.1128/jb.166.2.392-398.1986. [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. Harayama S., Mermod N., Rekik M., Lehrbach P. R., Timmis K. N. Roles of the divergent branches of the meta-cleavage pathway in the degradation of benzoate and substituted benzoates. J Bacteriol. 1987 Feb;169(2):558–564. doi: 10.1128/jb.169.2.558-564.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Harayama S., Rekik M., Ngai K. L., Ornston L. N. Physically associated enzymes produce and metabolize 2-hydroxy-2,4-dienoate, a chemically unstable intermediate formed in catechol metabolism via meta cleavage in Pseudomonas putida. J Bacteriol. 1989 Nov;171(11):6251–6258. doi: 10.1128/jb.171.11.6251-6258.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Higson F. K., Focht D. D. Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepacia MB2 through the meta fission pathway. Appl Environ Microbiol. 1992 Aug;58(8):2501–2504. doi: 10.1128/aem.58.8.2501-2504.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Kutsuna M., Someda K., Morita K., Yamanouchi Y., Kurimoto T., Kawamura Y., Matsumura H. [Ischemic cerebral symptoms after subarachnoid hemorrhage due to aneurysmal rupture (author's transl)]. No Shinkei Geka. 1978 Jun;6(6):543–548. [PubMed] [Google Scholar]
  15. Layton A. C., Sanseverino J., Wallace W., Corcoran C., Sayler G. S. Evidence for 4-chlorobenzoic acid dehalogenation mediated by plasmids related to pSS50. Appl Environ Microbiol. 1992 Jan;58(1):399–402. doi: 10.1128/aem.58.1.399-402.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Lloyd-Jones G., de Jong C., Ogden R. C., Duetz W. A., Williams P. A. Recombination of the bph (Biphenyl) Catabolic Genes from Plasmid pWW100 and Their Deletion during Growth on Benzoate. Appl Environ Microbiol. 1994 Feb;60(2):691–696. doi: 10.1128/aem.60.2.691-696.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Sala-Trepat J. M., Evans W. C. The meta cleavage of catechol by Azotobacter species. 4-Oxalocrotonate pathway. Eur J Biochem. 1971 Jun 11;20(3):400–413. doi: 10.1111/j.1432-1033.1971.tb01406.x. [DOI] [PubMed] [Google Scholar]
  18. Shields M. S., Hooper S. W., Sayler G. S. Plasmid-mediated mineralization of 4-chlorobiphenyl. J Bacteriol. 1985 Sep;163(3):882–889. doi: 10.1128/jb.163.3.882-889.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Sondossi M., Sylvestre M., Ahmad D. Effects of chlorobenzoate transformation on the Pseudomonas testosteroni biphenyl and chlorobiphenyl degradation pathway. Appl Environ Microbiol. 1992 Feb;58(2):485–495. doi: 10.1128/aem.58.2.485-495.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]

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