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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 Lenke^1,*

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.

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^* 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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