A new 4-nitrotoluene degradation pathway in a Mycobacterium strain

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...

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Published in:Applied and environmental microbiology 1998-02, Vol.64 (2), p.446-452
Main Authors: SPIESS, T, DESIERE, F, FISCHER, P, SPAIN, J. C, KNACKMUSS, H.-J, LENKE, H
Format: Article
Language:English
Subjects:
Anaerobiosis
Bacteria
Biodegradation, Environmental
Biological and medical sciences
Biology of microorganisms of confirmed or potential industrial interest
Bioremediation
Biotechnology
Environmental and Public Health Microbiology
Fundamental and applied biological sciences. Psychology
Fungi
Metabolism
Mission oriented research
Mycobacterium - growth & development
Mycobacterium - metabolism
Physiology and metabolism
Soils
Toluene - analogs & derivatives
Toluene - metabolism
VOCs
Volatile organic compounds
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Summary: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 (lambda max, 385 nm) was tentatively identified as 2-amino-5-methylmuconic semialdehyde, formed from 6-amino-m-cresol by meta ring cleavage.
ISSN:0099-2240
1098-5336
DOI:10.1128/aem.64.2.446-452.1998