Abstract
A Pseudomonas sp. that was capable of growth on 1,2-dichlorobenzene (o-DCB) or chlorobenzene as a sole source of carbon and energy was isolated by selective enrichment from activated sludge. The initial steps involved in the degradation of o-DCB were investigated by isolation of metabolites, respirometry, and assay of enzymes in cell extracts. Extracts of o-DCB-grown cells converted radiolabeled o-DCB to 3,4-dichloro-cis-1,2-dihydroxycyclohexa-3,5-diene (o-DCB dihydrodiol). 3,4-Dichlorocatechol and o-DCB dihydrodiol accumulated in culture fluids of cells exposed to o-DCB. The results suggest that o-DCB is initially converted by a dioxygenase to a dihydrodiol, which is converted to 3,4-dichlorocatechol by an NAD+-dependent dehydrogenase. Ring cleavage of 3,4-dichlorocatechol is by a catechol 1,2-oxygenase to form 2,3-dichloro-cis,cis-muconate. Preliminary results indicate that chloride is eliminated during subsequent lactonization of the 2,3-dichloro-cis,cis-muconate, followed by hydrolysis to form 5-chloromaleylacetic acid.
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- 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]
- Chapman P. J., Ribbons D. W. Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida. J Bacteriol. 1976 Mar;125(3):985–998. doi: 10.1128/jb.125.3.985-998.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
- 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]
- 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]
- Evans W. C., Smith B. S., Fernley H. N., Davies J. I. Bacterial metabolism of 2,4-dichlorophenoxyacetate. Biochem J. 1971 May;122(4):543–551. doi: 10.1042/bj1220543. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Evans W. C., Smith B. S., Moss P., Fernley H. N. Bacterial metabolism of 4-chlorophenoxyacetate. Biochem J. 1971 May;122(4):509–517. doi: 10.1042/bj1220509. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gibson D. T., Hensley M., Yoshioka H., Mabry T. J. Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. Biochemistry. 1970 Mar 31;9(7):1626–1630. doi: 10.1021/bi00809a023. [DOI] [PubMed] [Google Scholar]
- 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]
- Klecka G. M., Gibson D. T. Inhibition of catechol 2,3-dioxygenase from Pseudomonas putida by 3-chlorocatechol. Appl Environ Microbiol. 1981 May;41(5):1159–1165. doi: 10.1128/aem.41.5.1159-1165.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Knackmuss H. J., Hellwig M. Utilization and cooxidation of chlorinated phenols by Pseudomonas sp. B 13. Arch Microbiol. 1978 Apr 27;117(1):1–7. doi: 10.1007/BF00689343. [DOI] [PubMed] [Google Scholar]
- Reineke W., Knackmuss H. J. Hybrid pathway for chlorobenzoate metabolism in Pseudomonas sp. B13 derivatives. J Bacteriol. 1980 May;142(2):467–473. doi: 10.1128/jb.142.2.467-473.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
- 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]
- Schmidt E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Conversion of chlorinated muconic acids into maleoylacetic acid. Biochem J. 1980 Oct 15;192(1):339–347. doi: 10.1042/bj1920339. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Schmidt E., Remberg G., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Halogenated muconic acids as intermediates. Biochem J. 1980 Oct 15;192(1):331–337. doi: 10.1042/bj1920331. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Schraa G., Boone M. L., Jetten M. S., van Neerven A. R., Colberg P. J., Zehnder A. J. Degradation of 1,4-dichlorobenzene by Alcaligenes sp. strain A175. Appl Environ Microbiol. 1986 Dec;52(6):1374–1381. doi: 10.1128/aem.52.6.1374-1381.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Smith P. K., Krohn R. I., Hermanson G. T., Mallia A. K., Gartner F. H., Provenzano M. D., Fujimoto E. K., Goeke N. M., Olson B. J., Klenk D. C. Measurement of protein using bicinchoninic acid. Anal Biochem. 1985 Oct;150(1):76–85. doi: 10.1016/0003-2697(85)90442-7. [DOI] [PubMed] [Google Scholar]
- 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]
- Stanier R. Y., Palleroni N. J., Doudoroff M. The aerobic pseudomonads: a taxonomic study. J Gen Microbiol. 1966 May;43(2):159–271. doi: 10.1099/00221287-43-2-159. [DOI] [PubMed] [Google Scholar]
- Subramanian V., Liu T. N., Yeh W. K., Gibson D. T. Toluene dioxygenase: purification of an iron-sulfur protein by affinity chromatography. Biochem Biophys Res Commun. 1979 Dec 14;91(3):1131–1139. doi: 10.1016/0006-291x(79)91998-3. [DOI] [PubMed] [Google Scholar]
- Subramanian V., Liu T. N., Yeh W. K., Narro M., Gibson D. T. Purification and properties of NADH-ferredoxinTOL reductase. A component of toluene dioxygenase from Pseudomonas putida. J Biol Chem. 1981 Mar 25;256(6):2723–2730. [PubMed] [Google Scholar]
- Subramanian V., Liu T. N., Yeh W. K., Serdar C. M., Wackett L. P., Gibson D. T. Purification and properties of ferredoxinTOL. A component of toluene dioxygenase from Pseudomonas putida F1. J Biol Chem. 1985 Feb 25;260(4):2355–2363. [PubMed] [Google Scholar]
- Yeh W. K., Gibson D. T., Liu T. N. Toluene dioxygenase: a multicomponent enzyme system. Biochem Biophys Res Commun. 1977 Sep 9;78(1):401–410. doi: 10.1016/0006-291x(77)91268-2. [DOI] [PubMed] [Google Scholar]
- de Bont J. A., Vorage M. J., Hartmans S., van den Tweel W. J. Microbial degradation of 1,3-dichlorobenzene. Appl Environ Microbiol. 1986 Oct;52(4):677–680. doi: 10.1128/aem.52.4.677-680.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]