Initial hydrogenation and extensive reduction of substituted 2,4-dinitrophenols.

Applied and Environmental Microbiology
H Lenke, Hans-Joachim Knackmuss

Abstract

Rhodococcus erythropolis HL 24-1 isolated as a 2,4-dinitrophenol-degrading organism can utilize 2-chloro-4,6-dinitrophenol as the sole nitrogen, carbon, and energy source under aerobic conditions. This compound is metabolized with liberation of stoichiometric amounts of chloride and nitrite. Under anaerobic conditions, 2,4-dinitrophenol was transiently accumulated in the culture fluid, indicating a reductive elimination of chloride. During aerobic bioconversion of 2-amino-4,6-dinitrophenol by R. erythropolis HL 24-1, a reductive elimination of nitrite leading to 2-amino-6-nitrophenol was observed. Elimination of chloride or nitrite by the initial formation of a hydride Meisenheimer complex is discussed. A methyl group in the ortho position of the 2,4-dinitrophenol gives rise to an extensive reduction of the aromatic ring under aerobic conditions. Thus, 2-methyl-4,6-dinitrophenol was shown to be converted to the two diastereomers of 4,6-dinitro-2-methylhexanoate as dead-end metabolites which were identified by spectroscopic methods.

References

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Sep 1, 1992·Applied and Environmental Microbiology·H Lenke, H J Knackmuss
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Mar 1, 1991·Applied and Environmental Microbiology·J C Spain, D T Gibson

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Citations

Apr 29, 2016·Microbiology and Molecular Biology Reviews : MMBR·Chris GreeningColin J Jackson
Dec 18, 2003·Journal of Bacteriology·Dang P NgaGesche S Heiss
Apr 14, 2012·Critical Reviews in Microbiology·Baljinder SinghKashmir Singh
Aug 2, 2011·Applied and Environmental Microbiology·Dhan PrakashB N Tiwary
Sep 4, 2001·Biotechnology & Genetic Engineering Reviews·C E FrenchN C Bruce
Feb 15, 2012·Applied Microbiology and Biotechnology·Pankaj Kumar AroraCh Venkata Ramana
Mar 22, 2008·FEMS Microbiology Reviews·María Dolores RoldánConrado Moreno-Vivián
May 2, 2000·Applied and Environmental Microbiology·S F NishinoJ C Spain
Jul 16, 1999·Critical Reviews in Microbiology·A De Schrijver, R De Mot
Apr 2, 1999·Applied and Environmental Microbiology·E KatsivelaR M Wittich

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