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Appl Environ Microbiol, April 1998, p. 1256-1263, Vol. 64, No. 4
0099-2240/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.

¹⁹F Nuclear Magnetic Resonance as a Tool To Investigate Microbial Degradation of Fluorophenols to Fluorocatechols and Fluoromuconates

Marelle G. Boersma,^1,* Tatiana Y. Dinarieva,^1,2 Wouter J. Middelhoven,³ Willem J. H. van Berkel,¹ Joel Doran,¹ Jacques Vervoort,¹ and Ivonne M. C. M. Rietjens¹

Laboratory of Biochemistry, Wageningen Agricultural University, 6703 HA Wageningen,¹ and Laboratory of Microbiology, Wageningen Agricultural University, 6703 CT Wageningen,³ The Netherlands, and Laboratory of Microbiology, Moscow University, Moscow 119899, Russia²

Received 9 September 1997/Accepted 20 January 1998

A method was developed to study the biodegradation and oxidative biodehalogenation of fluorinated phenols by ¹⁹F nuclear magnetic resonance (NMR). Characterization of the ¹⁹F NMR spectra of metabolite profiles of a series of fluorophenols, converted by purified phenol hydroxylase, catechol 1,2-dioxygenase, and/or by the yeast-like fungus Exophiala jeanselmei, provided possibilities for identification of the ¹⁹F NMR chemical shift values of fluorinated catechol and muconate metabolites. As an example, the ¹⁹F NMR method thus defined was used to characterize the time-dependent metabolite profiles of various halophenols in either cell extracts or in incubations with whole cells of E. jeanselmei. The results obtained for these two systems are similar, except for the level of muconates observed. Altogether, the results of the present study describe a ¹⁹F NMR method which provides an efficient tool for elucidating the metabolic pathways for conversion of fluorine-containing phenols by microorganisms, with special emphasis on possibilities for biodehalogenation and detection of the type of fluorocatechols and fluoromuconates involved. In addition, the method provides possibilities for studying metabolic pathways in vivo in whole cells.

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^* Corresponding author. Mailing address: Laboratory of Biochemistry, Agricultural University Wageningen, Dreijenlaan 3, 6703 HA Wageningen, The Netherlands. Phone: 31-317-482868. Fax: 31-317-484801. E-mail: Marelle.Boersma{at}P450.BC.WAU.NL.

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