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Applied and Environmental Microbiology, September 2003, p. 5636-5642, Vol. 69, No. 9
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.9.5636-5642.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.

Conversion of 2-Fluoromuconate to cis-Dienelactone by Purified Enzymes of Rhodococcus opacus 1cp

Inna P. Solyanikova,1,2 Olga V. Moiseeva,1,2 Sjef Boeren,2 Marelle G. Boersma,3 Marina P. Kolomytseva,1 Jacques Vervoort,2 Ivonne M. C. M. Rietjens,3 Ludmila A. Golovleva,1 and Willem J. H. van Berkel2*

G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region 142290, Russian Federation,1 Laboratory of Biochemistry, Wageningen University, 6703 HA Wageningen,2 Division of Toxicology, Wageningen University, 6703 HE Wageningen, The Netherlands3

Received 26 February 2003/ Accepted 1 July 2003

The present study describes the 19F nuclear magnetic resonance analysis of the conversion of 3-halocatechols to lactones by purified chlorocatechol 1,2-dioxygenase (ClcA2), chloromuconate cycloisomerase (ClcB2), and chloromuconolactone dehalogenase (ClcF) from Rhodococcus opacus 1cp grown on 2-chlorophenol. The 3-halocatechol substrates were produced from the corresponding 2-halophenols by either phenol hydroxylase from Trichosporon cutaneum or 2-hydroxybiphenyl 3-mono-oxygenase from Pseudomonas azelaica. Several fluoromuconates resulting from intradiol ring cleavage by ClcA2 were identified. ClcB2 converted 2-fluoromuconate to 5-fluoromuconolactone and 2-chloro-4-fluoromuconate to 2-chloro-4-fluoromuconolactone. Especially the cycloisomerization of 2-fluoromuconate is a new observation. ClcF catalyzed the dehalogenation of 5-fluoromuconolactone to cis-dienelactone. The ClcB2 and ClcF-mediated reactions are in line with the recent finding of a second cluster of chlorocatechol catabolic genes in R. opacus 1cp which provides a new route for the microbial dehalogenation of 3-chlorocatechol.

* Corresponding author. Mailing address: Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, 6703 HA Wageningen, The Netherlands. Phone: 31-317-482861. Fax: 31-317-484801. E-mail: willem.vanberkel{at}wur.nl.

Applied and Environmental Microbiology, September 2003, p. 5636-5642, Vol. 69, No. 9
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.9.5636-5642.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.





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