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Applied and Environmental Microbiology, January 2004, p. 174-181, Vol. 70, No. 1
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.1.174-181.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.

Metabolism of 2,2'- and 3,3'-Dihydroxybiphenyl by the Biphenyl Catabolic Pathway of Comamonas testosteroni B-356

M. Sondossi,1 D. Barriault,2 and M. Sylvestre2*

Department of Microbiology, Weber State University, Ogden, Utah 84408,1 Institut National de la Recherche Scientifique, INRS-Institut Armand-Frappier, Pointe-Claire, Québec, Canada H9R 1G62

Received 27 June 2003/ Accepted 6 October 2003

The purpose of this investigation was to examine the capacity of the biphenyl catabolic enzymes of Comamonas testosteroni B-356 to metabolize dihydroxybiphenyls symmetrically substituted on both rings. Data show that 3,3'-dihydroxybiphenyl is by far the preferred substrate for strain B-356. However, the dihydrodiol metabolite is very unstable and readily tautomerizes to a dead-end metabolite or is dehydroxylated by elimination of water. The tautomerization route is the most prominent. Thus, a very small fraction of the substrate is converted to other hydroxylated and acidic metabolites. Although 2,2'-dihydroxybiphenyl is a poor substrate for strain B-356 biphenyl dioxygenase, metabolites were produced by the biphenyl catabolic enzymes, leading to production of 2-hydroxybenzoic acid. Data show that the major route of metabolism involves, as a first step, a direct dehydroxylation of one of the ortho-substituted carbons to yield 2,3,2'-trihydroxybiphenyl. However, other metabolites resulting from hydroxylation of carbons 5 and 6 of 2,2'-dihydroxybiphenyl were also produced, leading to dead-end metabolites.

* Corresponding author. Mailing address: Institut National de la Recherche Scientifique, INRS-Institut Armand-Frappier, 245 Boul. Hymus, Pointe-Claire, Québec, Canada H9R 1G6. Phone: (514) 630-8800. Fax: (514) 630-8850. E-mail: michel.sylvestre{at}inrs-iaf.uquebec.ca.

Applied and Environmental Microbiology, January 2004, p. 174-181, Vol. 70, No. 1
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.1.174-181.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Barriault, D., Lepine, F., Mohammadi, M., Milot, S., Leberre, N., Sylvestre, M. (2004). Revisiting the Regiospecificity of Burkholderia xenovorans LB400 Biphenyl Dioxygenase toward 2,2'-Dichlorobiphenyl and 2,3,2',3'-Tetrachlorobiphenyl. J. Biol. Chem. 279: 47489-47496 [Abstract] [Full Text]  


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