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Literature summary extracted from

  • 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 (2008), Appl. Environ. Microbiol., 74, 6820-6823.
    View publication on PubMedView publication on EuropePMC

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.7.1.B1 0.013
-
 NADPH 250 nM enzyme in 50 mM potassium phosphate buffer Pseudomonas putida
1.7.1.B1 0.048
-
 2,4,6-trinitrotoluene 250 nM enzyme in 50 mM potassium phosphate buffer Pseudomonas putida

Organism

EC Number Organism UniProt Comment Textmining
1.7.1.B1 Pseudomonas putida Q88PD0
-
-
1.7.1.B1 Pseudomonas putida KT 2240 Q88PD0
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.7.1.B1 by nickel affinity chromatography and eluted with a continuous imidazole gradient Pseudomonas putida

Reaction

EC Number Reaction Comment Organism Reaction ID
1.7.1.B1 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 Pseudomonas putida
a
1.7.1.B1 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 Pseudomonas putida
a

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.7.1.B1 105
-
 pH 7.0 Pseudomonas putida

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.7.1.B1 2,4,6-trinitrotoluene + 2 NADPH + 2 H+
-
 Pseudomonas putida 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 ?
1.7.1.B1 2,4,6-trinitrotoluene + 2 NADPH + 2 H+
-
 Pseudomonas putida KT 2240 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 ?
1.7.1.B1 2,4,6-trinitrotoluene + 2 NADPH + 2 H+
-
 Pseudomonas putida 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 ?
1.7.1.B1 2,4,6-trinitrotoluene + 2 NADPH + 2 H+
-
 Pseudomonas putida KT 2240 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 ?

Synonyms

EC Number Synonyms Comment Organism
1.7.1.B1 XenB protein type II hydride transferase of the old yellow enzyme (OYE) family of flavoproteins Pseudomonas putida
1.7.1.B1 xenobiotic reductase B
-
 Pseudomonas putida

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.7.1.B1 25
-
 assay at Pseudomonas putida

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.7.1.B1 7
-
 assay at Pseudomonas putida