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Applied and Environmental Microbiology, December 2001, p. 5497-5505, Vol. 67, No. 12
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.12.5497-5505.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Identification of a Novel Metabolite in the Degradation of Pyrene by Mycobacterium sp. Strain AP1: Actions of the Isolate on Two- and Three-Ring Polycyclic Aromatic Hydrocarbons

Joaquim Vila,1 Zaira López,1 Jordi Sabaté,1 Cristina Minguillón,2 Anna M. Solanas,1 and Magdalena Grifoll1,*

Department of Microbiology1 and Department of Pharmacology and Therapeutic Chemistry,2 University of Barcelona, Barcelona, Spain

Received 5 June 2001/Accepted 20 September 2001

Mycobacterium sp. strain AP1 grew with pyrene as a sole source of carbon and energy. The identification of metabolites accumulating during growth suggests that this strain initiates its attack on pyrene by either monooxygenation or dioxygenation at its C-4, C-5 positions to give trans- or cis-4,5-dihydroxy-4,5-dihydropyrene, respectively. Dehydrogenation of the latter, ortho cleavage of the resulting diol to form phenanthrene 4,5-dicarboxylic acid, and subsequent decarboxylation to phenanthrene 4-carboxylic acid lead to degradation of the phenanthrene 4-carboxylic acid via phthalate. A novel metabolite identified as 6,6'-dihydroxy-2,2'-biphenyl dicarboxylic acid demonstrates a new branch in the pathway that involves the cleavage of both central rings of pyrene. In addition to pyrene, strain AP1 utilized hexadecane, phenanthrene, and fluoranthene for growth. Pyrene-grown cells oxidized the methylenic groups of fluorene and acenaphthene and catalyzed the dihydroxylation and ortho cleavage of one of the rings of naphthalene and phenanthrene to give 2-carboxycinnamic and diphenic acids, respectively. The catabolic versatility of strain AP1 and its use of ortho cleavage mechanisms during the degradation of polycyclic aromatic hydrocarbons (PAHs) give new insight into the role that pyrene-degrading bacterial strains may play in the environmental fate of PAH mixtures.

* Corresponding author. Mailing address: Department of Microbiology, University of Barcelona, Diagonal 645, 08028 Barcelona, Spain. Phone: 34 93 4035752. Fax: 34 93 4034629. E-mail: magda{at}bio.ub.es.

Applied and Environmental Microbiology, December 2001, p. 5497-5505, Vol. 67, No. 12
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.12.5497-5505.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.


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