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2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In adidtion the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In adidtion the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In adidtion the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In adidtion the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
-
-
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+ = N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
-
-
-
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1,2,3-trinitroglycerol + 2 NADPH + 2 H+
?
-
-
-
?
2,4,6-trinitrophenol + 2 NADPH + 2 H+
?
-
-
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
CB1954 + NADPH + H+
? + hydroxylamine + NADP+
-
-
-
-
?
cyclohexenone + NADPH + H+
?
glycerol trinitrate + NADPH + H+
?
N-ethylmaleimide + NADPH + H+
?
-
-
-
?
additional information
?
-
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
-
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
i.e. 2-hydroxylamino-2,6-dinitrotoluene. The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptibe to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form secondary diaryl hydroxylamines and secondary diarylamine with release of nitrite
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
i.e. 2-hydroxylamino-2,6-dinitrotoluene. The amount of N-hydroxy-2-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-4-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitrophenyl-hydroxylamine and eventually N-(2-methyl-3,5-dinitrophenyl)-N-4-methyl-3,5-dinitroaniline are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptibe to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form secondary diaryl hydroxylamines and secondary diarylamine with release of nitrite
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-2-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
-
-
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
i.e. 4-hydroxylamino-2,6-dinitrotoluene. The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methyl-3,5-dinitroaniline + 2 NADP+ + H2O
-
i.e. 4-hydroxylamino-2,6-dinitrotoluene. The amount of N-hydroxy-4-methyl-3,5-dinitroaniline is larger than the amount of N-hydroxy-2-methyl-3,5-dinitroaniline formed. In a further nonenzymatic reaction nitrite is released and N,N-bis-(3,5-dinitrotolyl)-hydroxylamine and eventually N,N-bis-(3,5-dinitrotolyl)-amine are produced. In addition the aromatic ring of 2,4,6-trinitrotoluene is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (monohydride and dihydride complexes) which also form the secondary diaryl hydroxylamines and the secondary diarylamine with release of nitrite
-
?
cyclohexenone + NADPH + H+
?
-
-
-
?
cyclohexenone + NADPH + H+
?
-
-
-
?
glycerol trinitrate + NADPH + H+
?
-
-
-
?
glycerol trinitrate + NADPH + H+
?
-
-
-
?
additional information
?
-
ability to reduce nitroaromatic compounds, enzyme demonstrates type I and type II hydride transferase activity and reduced the nitro groups of 2,4,6-trinitrotoluene to hydroxylaminodinitrotoluene derivatives. The condensations of the primary products of type I and type II hydride transferases react with each other to yield diarylamines and nitrite, the latter can be further reduced to ammonium and serves as a nitrogen source for microorganisms in vivo
-
-
?
additional information
?
-
-
the enzyme shows no reactivity with CB1954
-
-
-
additional information
?
-
ability to reduce nitroaromatic compounds, enzyme demonstrates type I and type II hydride transferase activity and reduced the nitro groups of 2,4,6-trinitrotoluene to hydroxylaminodinitrotoluene derivatives. The condensations of the primary products of type I and type II hydride transferases react with each other to yield diarylamines and nitrite, the latter can be further reduced to ammonium and serves as a nitrogen source for microorganisms in vivo
-
-
?
additional information
?
-
-
enzyme additionally catalyzes reduction of nitrobenzene, reaction of EC 1.7.1.16
-
-
?
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Van Dillewijn, P.; Wittich, R.M.; Caballero, A.; Ramos, J.L.
Subfunctionality of hydride transferases of the old yellow enzyme family of flavoproteins of Pseudomonas putida
Appl. Environ. Microbiol.
74
6703-6708
2008
Pseudomonas putida (Q88PD0), Pseudomonas putida KT 2240 (Q88PD0)
brenda
Van Dillewijn, P.; Wittich, R.M.; Caballero, A.; Ramos, J.L.
Type II hydride transferases from different microorganisms yield nitrite and diarylamines from polynitroaromatic compounds
Appl. Environ. Microbiol.
74
6820-6823
2008
Pseudomonas putida (Q88PD0), Pseudomonas putida KT 2240 (Q88PD0)
brenda
Wittich, R.M.; Haidour, A.; Van Dillewijn, P.; Ramos, J.L.
OYE flavoprotein reductases initiate the condensation of TNT-derived intermediates to secondary diarylamines and nitrite
Environ. Sci. Technol.
42
734-739
2008
Pseudomonas putida, Pseudomonas putida JLR11
brenda
Fetar, H.; Gilmour, C.; Klinoski, R.; Daigle, D.M.; Dean, C.R.; Poole, K.
mexEF-oprN multidrug efflux operon of Pseudomonas aeruginosa: regulation by the MexT activator in response to nitrosative stress and chloramphenicol
Antimicrob. Agents Chemother.
55
508-514
2011
Pseudomonas aeruginosa
brenda
Ho, E.; Kahng, H.; Oh, K.
Characterization of nitroreductase purified from TNT-degrading bacterium, Pseudomonas sp. HK-6
Korean J. Microbiol. Biotechnol.
32
230-237
2004
Pseudomonas sp.
-
brenda
Osorio, M.I.; Cabrera, M.A.; Gonzalez-Nilo, F.; Perez-Donoso, J.M.
Odd loop regions of XenA and XenB enzymes modulate their interaction with nitro-explosives compounds and provide structural support for their regioselectivity
J. Chem. Inf. Model.
59
3860-3870
2019
Pseudomonas putida (Q3ZDM6), Pseudomonas putida (Q88PD0), Pseudomonas putida
brenda
Ball, P.; Halliwell, J.; Anderson, S.; Gwenin, V.; Gwenin, C.
Evaluation of two xenobiotic reductases from Pseudomonas putida for their suitability for magnetic nanoparticle-directed enzyme prodrug therapy as a novel approach to cancer treatment
MicrobiologyOpen
9
e1110
2020
Pseudomonas putida
brenda
1.7.1.B1 xenobiotic reductase B
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