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

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.

journal_name

Appl Environ Microbiol

authors

Lenke H,Knackmuss H

doi

10.1128/AEM.62.3.784-790.1996

keywords:

subject

Has Abstract

pub_date

1996-03-01 00:00:00

pages

784-90

issue

3

eissn

0099-2240

issn

1098-5336

journal_volume

62

pub_type

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