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

: Lenke, H.; Knackmuss, H.-J.

Applied and environmental microbiology 62 (1996), No.3, pp.784-790 : Ill., Lit.
ISSN: 0099-2240
Journal Article
Fraunhofer IGB ()
hydrogenation; reduction; rhodococcus erythropolis; substituted 2,4-dinitrophenole

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 enery 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-methylhex-anoate as dead-end metabolites which were identified by spectroscopic methods.