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Applied and Environmental Microbiology, May 2000, p. 2148-2153, Vol. 66, No. 5
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.

Identification of Fluoropyrogallols as New Intermediates in Biotransformation of Monofluorophenols in Rhodococcus opacus 1cp

Zoya I. Finkelstein,1 Boris P. Baskunov,1 Marelle G. Boersma,2 Jacques Vervoort,2 Eugene L. Golovlev,1 Willem J. H. van Berkel,2 Ludmila A. Golovleva,1 and Ivonne M. C. M. Rietjens2,*

G. K. Skrybin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia,1 and Department of Biomolecular Sciences, Laboratory of Biochemistry, Wageningen University, NL-6703 HA Wageningen, The Netherlands2

Received 19 November 1999/Accepted 28 February 2000

The transformation of monofluorophenols by whole cells of Rhodococcus opacus 1cp was investigated, with special emphasis on the nature of hydroxylated intermediates formed. Thin-layer chromatography, mass spectrum analysis, and 19F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The 19F chemical shifts and proton-coupled splitting patterns of the fluorine resonances of the trihydroxyfluorobenzene products established that the trihydroxylated aromatic metabolites contained hydroxyl substituents on three adjacent carbon atoms. Thus, formation of 1,2,3-trihydroxy-4-fluorobenzene (4-fluoropyrogallol) from 2-fluorophenol and formation of 1,2,3-trihydroxy-5-fluorobenzene (5-fluoropyrogallol) from 3-fluorophenol and 4-fluorophenol were observed. These results indicate the involvement of fluoropyrogallols as previously unidentified metabolites in the biotransformation of monofluorophenols in R. opacus 1cp.

* Corresponding author. Mailing address: Department of Biomolecular Sciences, Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, NL-6703 HA Wageningen, The Netherlands. Phone: 31-317-482868. Fax: 31-317-484801. E-mail: ivonne.rietjens{at}P450.BC.WAU.NL.

Applied and Environmental Microbiology, May 2000, p. 2148-2153, Vol. 66, No. 5
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.


This article has been cited by other articles:

  • Solyanikova, I. P., Moiseeva, O. V., Boeren, S., Boersma, M. G., Kolomytseva, M. P., Vervoort, J., Rietjens, I. M. C. M., Golovleva, L. A., van Berkel, W. J. H. (2003). Conversion of 2-Fluoromuconate to cis-Dienelactone by Purified Enzymes of Rhodococcus opacus 1cp. Appl. Environ. Microbiol. 69: 5636-5642 [Abstract] [Full Text]  


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