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Applied and Environmental Microbiology, April 2001, p. 1551-1557, Vol. 67, No. 4
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.4.1551-1557.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Manuela Gesell,1,* Elke Hammer,1 Michael Specht,2 Wittko Francke,2 and Frieder Schauer1

Institut für Mikrobiologie und Molekularbiologie, Ernst-Moritz-Arndt-Universität, Greifswald D-17487,1 and Institut für Organische Chemie, Universität Hamburg, Hamburg D-20146,2 Germany

Received 30 August 2000/Accepted 25 January 2001

We examined the pathway by which the fungicide biphenyl is metabolized in the imperfect fungus Paecilomyces lilacinus. The initial oxidation yielded the three monohydroxylated biphenyls. Further hydroxylation occurred on the first and the second aromatic ring systems, resulting in the formation of five di- and trihydroxylated metabolites. The fungus could cleave the aromatic structures, resulting in the transformation of biphenyl via ortho-substituted dihydroxybiphenyl to six-ring fission products. All compounds were characterized by gas chromatography-mass spectroscopy and proton nuclear magnetic resonance spectroscopy. These compounds include 2-hydroxy-4-phenylmuconic acid and 2-hydroxy-4-(4'-hydroxyphenyl)-muconic acid, which were produced from 3,4-dihydroxybiphenyl and further transformed to the corresponding lactones 4-phenyl-2-pyrone-6-carboxylic acid and 4-(4'-hydroxyphenyl)-2-pyrone-6-carboxylic acid, which accumulated in large amounts. Two additional ring cleavage products were identified as (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)-acetic acid and [5-oxo-3-(4'-hydroxyphenyl)-2,5-dihydrofuran-2-yl]-acetic acid. We found that P. lilacinus has a high transformation capacity for biphenyl, which could explain this organism's tolerance to this fungicide.

* Corresponding author. Mailing address: Ernst-Moritz-Arndt-Universität Greifswald, Institut für Mikrobiologie und Molekularbiologie, F.-L.-Jahn-Str. 15, D-17487 Greifswald, Germany. Phone: 49-3834-864225. Fax: 49-3834-864202. E-mail: gesell{at}biologie.uni-greifswald.de.

Applied and Environmental Microbiology, April 2001, p. 1551-1557, Vol. 67, No. 4
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.4.1551-1557.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.


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Copyright © 2001 by the American Society for Microbiology. All rights reserved.