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Applied and Environmental Microbiology, March 2001, p. 1030-1034, Vol. 67, No. 3
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.3.1030-1034.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Fungal Metabolism of Toluene: Monitoring of Fluorinated Analogs by ¹⁹F Nuclear Magnetic Resonance Spectroscopy

Francesc X. Prenafeta-Boldú,^1,3,* Dion M. A. M. Luykx,^1,3 Jacques Vervoort,² and Jan A. M. de Bont³

Division of Industrial Microbiology, Wageningen University, 6700 EV Wageningen,¹ Laboratory of Biochemistry, Wageningen University, 6700 HB Wageningen,² and Friesland Coberco Dairy Foods, Corporate Research, 7400 AB Deventer,³ The Netherlands

Received 16 June 2000/Accepted 14 September 2000

We used isomeric fluorotoluenes as model substrates to study the catabolism of toluene by five deuteromycete fungi and one ascomycete fungus capable of growth on toluene as the sole carbon and energy source, as well as by two fungi (Cunninghamella echinulata and Aspergillus niger) that cometabolize toluene. Whole cells were incubated with 2-, 3-, and 4-fluorotoluene, and metabolites were characterized by ¹⁹F nuclear magnetic resonance. Oxidation of fluorotoluene by C. echinulata was initiated either at the aromatic ring, resulting in fluorinated o-cresol, or at the methyl group to form fluorobenzoate. The initial conversion of the fluorotoluenes by toluene-grown fungi occurred only at the side chain and resulted in fluorinated benzoates. The latter compounds were the substrate for the ring hydroxylation and, depending on the fluorine position, were further metabolized up to catecholic intermediates. From the ¹⁹F nuclear magnetic resonance metabolic profiles, we propose that diverse fungi that grow on toluene assimilate toluene by an initial oxidation of the methyl group.

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^* Corresponding author. Mailing address: Division of Industrial Microbiology, Department of Agrotechnology and Food Sciences, Wageningen University, P.O. Box 8129, 6700 EV Wageningen, The Netherlands. Phone: 31 317-483393. Fax: 31 317-484978. E-mail: Francesc.Prenafeta{at}imb.ftns.wag-ur.nl.

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Applied and Environmental Microbiology, March 2001, p. 1030-1034, Vol. 67, No. 3
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.3.1030-1034.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

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