This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Reprints and Permissions Copyright Information Books from ASM Press MicrobeWorld Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Arensdorf, J J Articles by Focht, D D Search for Related Content PubMed PubMed Citation Articles by Arensdorf, J J Articles by Focht, D D Agricola Articles by Arensdorf, J J Articles by Focht, D D

 Previous Article  |  Next Article 

Appl Environ Microbiol. 1994 August; 60(8): 2884-2889

Formation of chlorocatechol meta cleavage products by a pseudomonad during metabolism of monochlorobiphenyls.

J J Arensdorf and D D Focht

Environmental Toxicology Graduate Program, University of California, Riverside 92521.

ABSTRACT

Pseudomonas cepacia P166 was able to metabolize all monochlorobiphenyls to the respective chlorobenzoates. Although they transiently accumulated, the chlorobenzoate degradation intermediates were further metabolized to chlorocatechols, which in turn were meta cleaved. 2- and 3-Chlorobiphenyl both produced 3-chlorocatechol, which was transformed to an acyl halide upon meta cleavage. 3-Chlorocatechol metabolism was toxic to the cells and impeded monochlorobiphenyl metabolism. In the case of 2-chlorobiphenyl, toxicity was manifested as a diminished growth rate, which nevertheless effected rapid substrate utilization. In the case of 3-chlorobiphenyl, which generates 3-chlorocatechol more rapidly than does 2-chlorobiphenyl, toxicity was manifested as a decrease in viable cells during substrate utilization. 4-Chlorobenzoate was transformed to 4-chlorocatechol, which was metabolized by a meta cleavage pathway leading to dehalogenation. Chloride release from 4-chlorocatechol metabolism, however, was slow and did not coincide with rapid 4-chlorocatechol turnover. Growth experiments with strain P166 on monochlorobiphenyls illustrated the difficulties of working with hydrophobic substrates that generate toxic intermediates. Turbidity could not be used to measure the growth of bacteria utilizing monochlorobiphenyls because high turbidities were routinely measured from cultures with very low viable-cell counts.

---

Appl Environ Microbiol. 1994 August; 60(8): 2884-2889

This article has been cited by other articles:

• Liu, S., Ogawa, N., Senda, T., Hasebe, A., Miyashita, K. (2005). Amino Acids in Positions 48, 52, and 73 Differentiate the Substrate Specificities of the Highly Homologous Chlorocatechol 1,2-Dioxygenases CbnA and TcbC. J. Bacteriol. 187: 5427-5436 [Abstract] [Full Text]  
• Ohnishi, K., Okuta, A., Ju, J., Hamada, T., Misono, H., Harayama, S. (2004). Molecular Breeding of 2,3-Dihydroxybiphenyl 1,2-Dioxygenase for Enhanced Resistance to 3-Chlorocatechol. J Biochem 135: 305-317 [Abstract] [Full Text]  
• Hatta, T., Mukerjee-Dhar, G., Damborsky, J., Kiyohara, H., Kimbara, K. (2003). Characterization of a Novel Thermostable Mn(II)-dependent 2,3-Dihydroxybiphenyl 1,2-Dioxygenase from a Polychlorinated Biphenyl- and Naphthalene-degrading Bacillus sp. JF8. J. Biol. Chem. 278: 21483-21492 [Abstract] [Full Text]  
• McKay, D. B., Prucha, M., Reineke, W., Timmis, K. N., Pieper, D. H. (2003). Substrate Specificity and Expression of Three 2,3-Dihydroxybiphenyl 1,2-Dioxygenases from Rhodococcus globerulus Strain P6. J. Bacteriol. 185: 2944-2951 [Abstract] [Full Text]  
• Vaillancourt, F. H., Haro, M.-A., Drouin, N. M., Karim, Z., Maaroufi, H., Eltis, L. D. (2003). Characterization of Extradiol Dioxygenases from a Polychlorinated Biphenyl-Degrading Strain That Possess Higher Specificities for Chlorinated Metabolites. J. Bacteriol. 185: 1253-1260 [Abstract] [Full Text]  
• Mars, A. E., Kingma, J., Kaschabek, S. R., Reineke, W., Janssen, D. B. (1999). Conversion of 3-Chlorocatechol by Various Catechol 2,3-Dioxygenases and Sequence Analysis of the Chlorocatechol Dioxygenase Region of Pseudomonas putida GJ31. J. Bacteriol. 181: 1309-1318 [Abstract] [Full Text]  
• Riegert, U., Heiss, G., Fischer, P., Stolz, A. (1998). Distal Cleavage of 3-Chlorocatechol by an Extradiol Dioxygenase to 3-Chloro-2-Hydroxymuconic Semialdehyde. J. Bacteriol. 180: 2849-2853 [Abstract] [Full Text]  
• Kaschabek, S. R., Kasberg, T., Müller, D., Mars, A. E., Janssen, D. B., Reineke, W. (1998). Degradation of Chloroaromatics: Purification and Characterization of a Novel Type of Chlorocatechol 2,3-Dioxygenase of Pseudomonas putida GJ31. J. Bacteriol. 180: 296-302 [Abstract] [Full Text]  
• Vaillancourt, F. H., Labbe, G., Drouin, N. M., Fortin, P. D., Eltis, L. D. (2002). The Mechanism-based Inactivation of 2,3-Dihydroxybiphenyl 1,2-Dioxygenase by Catecholic Substrates. J. Biol. Chem. 277: 2019-2027 [Abstract] [Full Text]