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Applied and Environmental Microbiology, June 1999, p. 2317-2323, Vol. 65, No. 6
0099-2240/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.

Chemoselective Nitro Group Reduction and Reductive Dechlorination Initiate Degradation of 2-Chloro-5-Nitrophenol by Ralstonia eutropha JMP134

Andreas Schenzle,1,2,dagger Hiltrud Lenke,1 Jim C. Spain,3 and Hans-Joachim Knackmuss1,2,*

Fraunhofer-Institut für Grenzflächen- und Bioverfahrenstechnik1 and Institut für Mikrobiologie der Universität Stuttgart,2 D-70569 Stuttgart, Germany, and Armstrong Laboratory, AFRL/MRLQ, Tyndall Air Force Base, Florida 32403-53193

Received 25 November 1998/Accepted 29 March 1999

Ralstonia eutropha JMP134 utilizes 2-chloro-5-nitrophenol as a sole source of nitrogen, carbon, and energy. The initial steps for degradation of 2-chloro-5-nitrophenol are analogous to those of 3-nitrophenol degradation in R. eutropha JMP134. 2-Chloro-5-nitrophenol is initially reduced to 2-chloro-5-hydroxylaminophenol, which is subject to an enzymatic Bamberger rearrangement yielding 2-amino-5-chlorohydroquinone. The chlorine of 2-amino-5-chlorohydroquinone is removed by a reductive mechanism, and aminohydroquinone is formed. 2-Chloro-5-nitrophenol and 3-nitrophenol induce the expression of 3-nitrophenol nitroreductase, of 3-hydroxylaminophenol mutase, and of the dechlorinating activity. 3-Nitrophenol nitroreductase catalyzes chemoselective reduction of aromatic nitro groups to hydroxylamino groups in the presence of NADPH. 3-Nitrophenol nitroreductase is active with a variety of mono-, di-, and trinitroaromatic compounds, demonstrating a relaxed substrate specificity of the enzyme. Nitrosobenzene serves as a substrate for the enzyme and is converted faster than nitrobenzene.

* Corresponding author. Mailing address: Institut für Mikrobiologie der Universität Stuttgart, Allmandring 31, D-70569 Stuttgart, Germany. Phone: (49) 711 685 5487. Fax: (49) 711 685 5725. E-mail: imbhjk{at}po.uni-stuttgart.de.

dagger Present address: DuPont Company, Central Research & Development Dept., E328/B48a Experimental Station, Wilmington, DE 19898.

Applied and Environmental Microbiology, June 1999, p. 2317-2323, Vol. 65, No. 6
0099-2240/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.


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