A New 4-Nitrotoluene Degradation Pathway in a <i>Mycobacterium</i> Strain

DOI Web Site 被引用文献1件
  • Tilmann Spiess
    <!--label omitted: 1-->Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik,1
  • Frank Desiere
    <!--label omitted: 1-->Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik,1
  • Peter Fischer
    <!--label omitted: 3-->Institut für Organische Chemie der Universität Stuttgart,3 D-70569 Stuttgart, Germany, and
  • Jim C. Spain
    <!--label omitted: 4-->Armstrong Laboratory/EQ-OL, Tyndall Air Force Base, Florida 32403-53234
  • Hans-Joachim Knackmuss
    <!--label omitted: 1-->Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik,1
  • Hiltrud Lenke
    <!--label omitted: 1-->Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik,1

書誌事項

公開日
1998-02
権利情報
  • https://journals.asm.org/non-commercial-tdm-license
DOI
  • 10.1128/aem.64.2.446-452.1998
公開者
American Society for Microbiology

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説明

<jats:title>ABSTRACT</jats:title> <jats:p> <jats:italic>Mycobacterium</jats:italic> sp. strain HL 4-NT-1, isolated from a mixed soil sample from the Stuttgart area, utilized 4-nitrotoluene as the sole source of nitrogen, carbon, and energy. Under aerobic conditions, resting cells of the <jats:italic>Mycobacterium</jats:italic> strain metabolized 4-nitrotoluene with concomitant release of small amounts of ammonia; under anaerobic conditions, 4-nitrotoluene was completely converted to 6-amino- <jats:italic>m</jats:italic> -cresol. 4-Hydroxylaminotoluene was converted to 6-amino- <jats:italic>m</jats:italic> -cresol by cell extracts and thus could be confirmed as the initial metabolite in the degradative pathway. This enzymatic equivalent to the acid-catalyzed Bamberger rearrangement requires neither cofactors nor oxygen. In the same crucial enzymatic step, the homologous substrate hydroxylaminobenzene was rearranged to 2-aminophenol. Abiotic oxidative dimerization of 6-amino- <jats:italic>m</jats:italic> -cresol, observed during growth of the <jats:italic>Mycobacterium</jats:italic> strain, yielded a yellow dihydrophenoxazinone. Another yellow metabolite (λ <jats:sub>max</jats:sub> , 385 nm) was tentatively identified as 2-amino-5-methylmuconic semialdehyde, formed from 6-amino- <jats:italic>m</jats:italic> -cresol by <jats:italic>meta</jats:italic> ring cleavage. </jats:p>

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