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  4. Chemoselective nitro group reduction and reductive dechlorination initiate degradation of 2-chloro-5-nitrophenol by Ralstonia eutropha JMP134
 
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1999
Journal Article
Title

Chemoselective nitro group reduction and reductive dechlorination initiate degradation of 2-chloro-5-nitrophenol by Ralstonia eutropha JMP134

Abstract
Ralstonia eutropha JMP134 utilizes 2-chloro-5-nitrophenol as a sole source of nitrogen, carbon, and energy. The initial steps for degradation of 2-chloro-5-nitrophenol are analogous to those of 3-nitrophenol degradation in R. eutropha JMP134. 2-Chloro-5-nitrophenol is initially reduced to 2-chloro-5-hydroxylaminophenol, which is subject to an enzymatic Bamberger rearrangement yielding 2-amino-5-chlorohydroquinone. The chlorine of 2-amino-5-chlorohydroquinone is removed by a reductive mechanism, and aminohydroquinone is formed. 2-Chloro-5-nitrophenol and 3-nitrophenol induce the expression of 3-nitrophenol nitroreductase, of 3-hydroxylaminophenol mutase, and of the dechlorinating activity. 3-Nitrophenol nitroreductase catalyzes chemoselective reduction of aromatic nitro groups to hydroxylamino groups in the presence of NADPH. 3-Nitrophenol nitroreductase is active with a variety of mono-, di-, and trinitroaromatic compounds, demonstrating a relaxed substrate specificity of the enzyme. N itrosobenzene serves as a substrate for the enzyme and is converted faster than nitrobenzene.
Author(s)
Schenzle, Andreas.  
Lenke, H.  
Spain, J.C.
Knackmuss, H.-J.  
Journal
Applied and environmental microbiology  
Language
English
Fraunhofer-Institut für Grenzflächen- und Bioverfahrenstechnik IGB  
Keyword(s)
  • 2-chloro-5-nitrophenol degradation

  • biodegradation

  • nitro group reduction

  • Ralstonia eutropha JMP134

  • reductive dechlorination

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