Initial Reductive Reactions in Aerobic Microbial Metabolism of 2,4,6-Trinitrotoluene

@article{Vorbeck1998InitialRR,
  title={Initial Reductive Reactions in Aerobic Microbial Metabolism of 2,4,6-Trinitrotoluene},
  author={C. Vorbeck and H. Lenke and Peter Q Fischer and J. Spain and H. Knackmuss},
  journal={Applied and Environmental Microbiology},
  year={1998},
  volume={64},
  pages={246 - 252}
}
ABSTRACT Because of its high electron deficiency, initial microbial transformations of 2,4,6-trinitrotoluene (TNT) are characterized by reductive rather than oxidation reactions. The reduction of the nitro groups seems to be the dominating mechanism, whereas hydrogenation of the aromatic ring, as described for picric acid, appears to be of minor importance. Thus, two bacterial strains enriched with TNT as a sole source of nitrogen under aerobic conditions, a gram-negative strain called TNT-8… Expand
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References

SHOWING 1-10 OF 52 REFERENCES
[Transformation of 2,4,6-trinitrotoluene during oxygen and nitrate respiration in Pseudomonas fluorescens].
: A study of the metabolic pathway and the rate of 2,4,6-trinitrotoluene (TNT) transformation depending on the nature of the electron acceptor in the electron transport chain of PseudomonasExpand
Biodegradation of 2,4-dinitrotoluene by a Pseudomonas sp.
TLDR
The results indicate an initial dioxygenase attack at the 4,5 position of DNT with the concomitant release of nitrite leads to complete biodegradation and removal of the second nitro group as nitrite. Expand
Anaerobic transformation of 2,4,6-TNT and related nitroaromatic compounds by Clostridium acetobutylicum
The transformation of TNT and related aminated nitrotoluenes by Clostridium acetobutylicum was investigated. 2,4,6-trinitrotoluene (TNT) was rapidly reduced (537 nM min−1 mg protein−1) toExpand
Transformation of 2,4,6-Trinitrotoluene by Pseudomonas pseudoalcaligenes JS52
TLDR
The unusual ability of the nitrobenzene nitroreductase to catalyze the stoichiometric reduction of aromatic nitro compounds to the corresponding hydroxylamine provides the basis for the novel pathway for metabolism of TNT. Expand
Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds
TLDR
A variety of nitroaromatic compounds, including 2,4,6-trinitrotoluene (TNT), were reduced by hydrogen in the presence of enzyme preparations from Veillonella alkalescens, indicating the question of whether ferredoxin acts as a nonspecific reductase for nitroARomatic compounds remains unresolved. Expand
Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes
TLDR
Results indicate that the catabolic pathway involves the reduction of nitrobenzene to nitrosobenzenes and then to hydroxylaminobenzene; each of these steps requires 1 mol of NADPH. Expand
Catabolism of 3-Nitrophenol by Ralstonia eutropha JMP 134
TLDR
Ralstonia eutropha JMP 134 utilizes 3-nitrophenol as the sole source of nitrogen, carbon, and energy and enzyme-mediated transformation corresponds to the acid-catalyzed Bamberger rearrangement. Expand
Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene
TLDR
All bacteria in this study, in addition to removing nitro groups from TNT, reducedNitro groups on the aromatic ring via hydroxylamine to amino derivatives, were reduced in order to grow on TNT as the sole C and N source. Expand
A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas.
TLDR
It is proposed that the pathway for 4NT catabolism proceeds via 4NBA, 4 NBZ and 4NBZate and ultimately to protocatechuate with release of the nitro group as ammonium. Expand
Identification of Products Resulting from the Biological Reduction of 2,4,6-Trinitrotoluene, 2,4-Dinitrotoluene, and 2,6-Dinitrotoluene by Pseudomonas sp.
Pseudomonas sp. clone A is able to use 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene, and 2,6-dinitrotoluene as an N-source after the enzymatic removal of nitro groups from the aromatic ring. WeExpand
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