Skip to main content
NCBI home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1995 Jan;177(1):20–26. doi: 10.1128/jb.177.1.20-26.1995

Dihydroxylation and dechlorination of chlorinated biphenyls by purified biphenyl 2,3-dioxygenase from Pseudomonas sp. strain LB400.

J D Haddock 1, J R Horton 1, D T Gibson 1
PMCID: PMC176551  PMID: 8002618

Abstract

Oxidation of biphenyl and nine chlorinated biphenyls (CBs) by the biphenyl 2,3-dioxygenase from Pseudomonas sp. strain LB400 was examined. The purified terminal oxygenase required the addition of partially purified electron transport components, NAD(P)H, and ferrous iron to oxidize biphenyl and CBs. cis-Biphenyl 2,3-dihydrodiol was produced with biphenyl as the substrate. Dihydrodiols were produced from all CBs, and more than one compound was produced with most substrates. Catechols were produced when the dioxygenase-catalyzed reaction occurred at the 2,3 position of a 2-chlorophenyl ring, resulting in dechlorination of the substrate. Oxidation at the 3,4 position of a 2,5-dichlorophenyl ring produced a 3,4-dihydrodiol. Compounds resulting from both types of reaction were produced during oxidation of 2,5,2'-trichlorobiphenyl. The broad substrate specificity and the ability to oxidize at different ring positions suggest that the biphenyl 2,3-dioxygenase is responsible for the wide range of CBs oxidized by Pseudomonas sp. strain LB400.

Full Text

The Full Text of this article is available as a PDF (228.2 KB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. 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]
  2. Bedard D. L., Haberl M. L., May R. J., Brennan M. J. Evidence for novel mechanisms of polychlorinated biphenyl metabolism in Alcaligenes eutrophus H850. Appl Environ Microbiol. 1987 May;53(5):1103–1112. doi: 10.1128/aem.53.5.1103-1112.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Bedard D. L., Unterman R., Bopp L. H., Brennan M. J., Haberl M. L., Johnson C. Rapid assay for screening and characterizing microorganisms for the ability to degrade polychlorinated biphenyls. Appl Environ Microbiol. 1986 Apr;51(4):761–768. doi: 10.1128/aem.51.4.761-768.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Bedard D. L., Wagner R. E., Brennan M. J., Haberl M. L., Brown J. F., Jr Extensive degradation of Aroclors and environmentally transformed polychlorinated biphenyls by Alcaligenes eutrophus H850. Appl Environ Microbiol. 1987 May;53(5):1094–1102. doi: 10.1128/aem.53.5.1094-1102.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1016/0003-2697(76)90527-3. [DOI] [PubMed] [Google Scholar]
  6. Catelani D., Colombi A., Sorlini C., Treccani V. Metabolism of biphenyl. 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate: the meta-cleavage product from 2,3-dihydroxybiphenyl by Pseudomonas putida. Biochem J. 1973 Aug;134(4):1063–1066. doi: 10.1042/bj1341063. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. 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]
  8. Erickson B. D., Mondello F. J. Enhanced biodegradation of polychlorinated biphenyls after site-directed mutagenesis of a biphenyl dioxygenase gene. Appl Environ Microbiol. 1993 Nov;59(11):3858–3862. doi: 10.1128/aem.59.11.3858-3862.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Erickson B. D., Mondello F. J. Nucleotide sequencing and transcriptional mapping of the genes encoding biphenyl dioxygenase, a multicomponent polychlorinated-biphenyl-degrading enzyme in Pseudomonas strain LB400. J Bacteriol. 1992 May;174(9):2903–2912. doi: 10.1128/jb.174.9.2903-2912.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Fetzner S., Müller R., Lingens F. Purification and some properties of 2-halobenzoate 1,2-dioxygenase, a two-component enzyme system from Pseudomonas cepacia 2CBS. J Bacteriol. 1992 Jan;174(1):279–290. doi: 10.1128/jb.174.1.279-290.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Furukawa K., Hayase N., Taira K., Tomizuka N. Molecular relationship of chromosomal genes encoding biphenyl/polychlorinated biphenyl catabolism: some soil bacteria possess a highly conserved bph operon. J Bacteriol. 1989 Oct;171(10):5467–5472. doi: 10.1128/jb.171.10.5467-5472.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Furukawa K., Tomizuka N., Kamibayashi A. Effect of chlorine substitution on the bacterial metabolism of various polychlorinated biphenyls. Appl Environ Microbiol. 1979 Aug;38(2):301–310. doi: 10.1128/aem.38.2.301-310.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Furukawa K., Tonomura K., Kamibayashi A. Effect of chlorine substitution on the biodegradability of polychlorinated biphenyls. Appl Environ Microbiol. 1978 Feb;35(2):223–227. doi: 10.1128/aem.35.2.223-227.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Gibson D. T., Cruden D. L., Haddock J. D., Zylstra G. J., Brand J. M. Oxidation of polychlorinated biphenyls by Pseudomonas sp. strain LB400 and Pseudomonas pseudoalcaligenes KF707. J Bacteriol. 1993 Jul;175(14):4561–4564. doi: 10.1128/jb.175.14.4561-4564.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. 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]
  16. Haddock J. D., Nadim L. M., Gibson D. T. Oxidation of biphenyl by a multicomponent enzyme system from Pseudomonas sp. strain LB400. J Bacteriol. 1993 Jan;175(2):395–400. doi: 10.1128/jb.175.2.395-400.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Markus A., Klages U., Krauss S., Lingens F. Oxidation and dehalogenation of 4-chlorophenylacetate by a two-component enzyme system from Pseudomonas sp. strain CBS3. J Bacteriol. 1984 Nov;160(2):618–621. doi: 10.1128/jb.160.2.618-621.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Mondello F. J. Cloning and expression in Escherichia coli of Pseudomonas strain LB400 genes encoding polychlorinated biphenyl degradation. J Bacteriol. 1989 Mar;171(3):1725–1732. doi: 10.1128/jb.171.3.1725-1732.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Nakatsu C. H., Wyndham R. C. Cloning and expression of the transposable chlorobenzoate-3,4-dioxygenase genes of Alcaligenes sp. strain BR60. Appl Environ Microbiol. 1993 Nov;59(11):3625–3633. doi: 10.1128/aem.59.11.3625-3633.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Romanov V., Hausinger R. P. Pseudomonas aeruginosa 142 uses a three-component ortho-halobenzoate 1,2-dioxygenase for metabolism of 2,4-dichloro- and 2-chlorobenzoate. J Bacteriol. 1994 Jun;176(11):3368–3374. doi: 10.1128/jb.176.11.3368-3374.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Taira K., Hirose J., Hayashida S., Furukawa K. Analysis of bph operon from the polychlorinated biphenyl-degrading strain of Pseudomonas pseudoalcaligenes KF707. J Biol Chem. 1992 Mar 5;267(7):4844–4853. [PubMed] [Google Scholar]
  22. Yates J. R., Mondello F. J. Sequence similarities in the genes encoding polychlorinated biphenyl degradation by Pseudomonas strain LB400 and Alcaligenes eutrophus H850. J Bacteriol. 1989 Mar;171(3):1733–1735. doi: 10.1128/jb.171.3.1733-1735.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES