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Applied and Environmental Microbiology, May 2004, p. 2854-2860, Vol. 70, No. 5
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.5.2854-2860.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.

Nitrite Elimination and Hydrolytic Ring Cleavage in 2,4,6-Trinitrophenol (Picric Acid) Degradation

Klaus W. Hofmann, Hans-Joachim Knackmuss, and Gesche Heiss*

Institute of Microbiology, University of Stuttgart, 70569 Stuttgart, Germany

Received 3 June 2003/ Accepted 10 February 2004

Two hydrogenation reactions in the initial steps of degradation of 2,4,6-trinitrophenol produce the dihydride Meisenheimer complex of 2,4,6-trinitrophenol. The npdH gene (contained in the npd gene cluster of the 2,4,6-trinitrophenol-degrading strain Rhodococcus opacus HL PM-1) was shown here to encode a tautomerase, catalyzing a proton shift between the aci-nitro and the nitro forms of the dihydride Meisenheimer complex of 2,4,6-trinitrophenol. An enzyme (which eliminated nitrite from the aci-nitro form but not the nitro form of the dihydride complex of 2,4,6-trinitrophenol) was purified from the 2,4,6-trinitrophenol-degrading strain Nocardioides simplex FJ2-1A. The product of nitrite release was the hydride Meisenheimer complex of 2,4-dinitrophenol, which was hydrogenated to the dihydride Meisenheimer complex of 2,4-dinitrophenol by the hydride transferase I and the NADPH-dependent F420 reductase from strain HL PM-1. At pH 7.5, the dihydride complex of 2,4-dinitrophenol is protonated to 2,4-dinitrocyclohexanone. A hydrolase was purified from strain FJ2-1A and shown to cleave 2,4-dinitrocyclohexanone hydrolytically to 4,6-dinitrohexanoate.

* Corresponding author. Mailing address: Institute of Microbiology, University of Stuttgart, Allmandring 31, 70569 Stuttgart, Germany. Phone: 49 711 685 5491. Fax: 49 711 685 5725. E-mail: imbgh{at}po.uni-stuttgart.de.

Applied and Environmental Microbiology, May 2004, p. 2854-2860, Vol. 70, No. 5
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.5.2854-2860.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.



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