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Appl Environ Microbiol, February 1998, p. 446-452, Vol. 64, No. 2
0099-2240/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.
A New 4-Nitrotoluene Degradation Pathway in a
Mycobacterium Strain
Tilmann
Spiess,1,2
Frank
Desiere,1,
Peter
Fischer,3
Jim C.
Spain,4
Hans-Joachim
Knackmuss,1,2 and
Hiltrud
Lenke1,*
Fraunhofer Institut für
Grenzflächen- und Bioverfahrenstechnik,1
Institut für Mikrobiologie der Universität
Stuttgart,2 and
Institut für
Organische Chemie der Universität
Stuttgart,3 D-70569 Stuttgart, Germany,
and
Armstrong Laboratory/EQ-OL, Tyndall Air Force Base,
Florida 32403-53234
Received 11 August 1997/Accepted 11 November 1997
Mycobacterium 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 Mycobacterium strain
metabolized 4-nitrotoluene with concomitant release of small amounts of
ammonia; under anaerobic conditions, 4-nitrotoluene was completely
converted to 6-amino-m-cresol. 4-Hydroxylaminotoluene was
converted to 6-amino-m-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-m-cresol, observed during growth of the
Mycobacterium strain, yielded a yellow
dihydrophenoxazinone. Another yellow metabolite (
max,
385 nm) was tentatively identified as 2-amino-5-methylmuconic semialdehyde, formed from 6-amino-m-cresol by
meta ring cleavage.
*
Corresponding author. Mailing address: Fraunhofer
Institut für Grenzflächen- und Bioverfahrenstechnik,
Nobelstr. 12, D-70569 Stuttgart, Germany. Phone: (49) 711 970 4216. Fax: (49) 711 970 4200. E-mail: len{at}igb.fhg.de.

Present address: Nestle Research Center, CH-1000 Lausanne 26, Switzerland.
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