This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrowReprints and Permissions
Right arrow Copyright Information
Right arrow Books from ASM Press
Right arrow MicrobeWorld
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Rieger, P.-G.
Right arrow Articles by Knackmuss, H.-J.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Rieger, P.-G.
Right arrow Articles by Knackmuss, H.-J.

 Previous Article  |  Next Article 

Journal of Bacteriology, February 1999, p. 1189-1195, Vol. 181, No. 4
0021-9193/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.

Hydride-Meisenheimer Complex Formation and Protonation as Key Reactions of 2,4,6-Trinitrophenol Biodegradation by Rhodococcus erythropolis

Paul-Gerhard Rieger,1 Volker Sinnwell,2 Andrea Preuß,1 Wittko Francke,2 and Hans-Joachim Knackmuss1,*

Institut für Mikrobiologie der Universität Stuttgart, D-70569 Stuttgart,1 and Institut für Organische Chemie der Universität Hamburg, D-20146 Hamburg,2 Germany

Received 6 October 1998/Accepted 10 December 1998

Biodegradation of 2,4,6-trinitrophenol (picric acid) by Rhodococcus erythropolis HLPM-1 proceeds via initial hydrogenation of the aromatic ring system. Here we present evidence for the formation of a hydride-Meisenheimer complex (anionic sigma -complex) of picric acid and its protonated form under physiological conditions. These complexes are key intermediates of denitration and productive microbial degradation of picric acid. For comparative spectroscopic identification of the hydride complex, it was necessary to synthesize this complex for the first time. Spectroscopic data revealed the initial addition of a hydride ion at position 3 of picric acid. This hydride complex readily picks up a proton at position 2, thus forming a reactive species for the elimination of nitrite. Cell extracts of R. erythropolis HLPM-1 transform the chemically synthesized hydride complex into 2,4-dinitrophenol. Picric acid is used as the sole carbon, nitrogen, and energy source by R. erythropolis HLPM-1.

* Corresponding author. Mailing address: Institut für Mikrobiologie, Universität Stuttgart, Allmandring 31, D-70569 Stuttgart, Germany. Phone: (49) 711 6855487. Fax: (49) 711 6855725. E-mail: imbhjk{at}po.uni-stuttgart.de.

Journal of Bacteriology, February 1999, p. 1189-1195, Vol. 181, No. 4
0021-9193/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.


This article has been cited by other articles:

  • Hofmann, K. W., Knackmuss, H.-J., Heiss, G. (2004). Nitrite Elimination and Hydrolytic Ring Cleavage in 2,4,6-Trinitrophenol (Picric Acid) Degradation. Appl. Environ. Microbiol. 70: 2854-2860 [Abstract] [Full Text]  
  • Heiss, G., Hofmann, K. W., Trachtmann, N., Walters, D. M., Rouviere, P., Knackmuss, H.-J. (2002). npd gene functions of Rhodococcus (opacus) erythropolis HL PM-1 in the initial steps of 2,4,6-trinitrophenol degradation. Microbiology 148: 799-806 [Abstract] [Full Text]  
  • Esteve-Nunez, A., Caballero, A., Ramos, J. L. (2001). Biological Degradation of 2,4,6-Trinitrotoluene. Microbiol. Mol. Biol. Rev. 65: 335-352 [Abstract] [Full Text]  
  • Ebert, S., Rieger, P.-G., Knackmuss, H.-J. (1999). Function of Coenzyme F420 in Aerobic Catabolism of 2,4,6-Trinitrophenol and 2,4-Dinitrophenol by Nocardioides simplex FJ2-1A. J. Bacteriol. 181: 2669-2674 [Abstract] [Full Text]  


Copyright © 2009 by the American Society for Microbiology.   For an alternate route to Journals.ASM.org, visit: http://intl-journals.asm.org | More Info»