Information on EC 1.14.12.B3 - 2,4-dinitrotoluene dioxygenase [NADH]

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The expected taxonomic range for this enzyme is: Burkholderia

EC NUMBER
COMMENTARY hide
1.14.12.B3
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
2,4-dinitrotoluene dioxygenase [NADH]
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SYSTEMATIC NAME
IUBMB Comments
2,4-nitrotoluene,NADH:oxygen oxidoreductase (4,5-hydroxylating, denitrifying)
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,4-dinitrotoluene + NADH + H+ + O2
4-methyl-5-nitrocatechol + nitrite + NAD+
show the reaction diagram
2,4-dinitrotoluene + NADH + O2
4-methyl-5-nitrocatechol + nitrite + NAD+
show the reaction diagram
2-amino-3-nitrotoluene + NADH + O2
2-amino-3-nitrobenzylalcohol + nitrite + NAD+
show the reaction diagram
2-amino-5-nitrotoluene + NADH + O2
2-amino-5-nitrobenzylalcohol + aminonitrocresol + nitrite + NAD+
show the reaction diagram
2-amino-6-nitrotoluene + NADH + O2
2-amino-4-nitro-m-cresol + 3-amino-5-nitro-p-cresol + nitrite + NAD+
show the reaction diagram
3-amino-4-nitrotoluene + NADH + O2
3-amino-4-nitrobenzylalcohol + aminonitrocresol + nitrite + NAD+
show the reaction diagram
3-nitrotoluene + NADH + O2
4-methylcatechol + nitrite + NAD+
show the reaction diagram
4-amino-2-nitrotoluene + NADH + O2
aminonitrocresol + nitrite + NAD+
show the reaction diagram
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13% yield
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?
4-amino-3-nitrotoluene + NADH + O2
4-amino-3-nitrobenzylalcohol + aminonitrocresol + nitrite + NAD+
show the reaction diagram
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19% yield
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?
5-amino-2-nitrotoluene + NADH + O2
2-amino-5-nitro-o-cresol + nitrite + NAD+
show the reaction diagram
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24% yield
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?
indan + NADH + H+ + O2
1-indanol + ? + NAD+
show the reaction diagram
indoline + NADH + H+ + O2
indigo + ? + NAD+
show the reaction diagram
m-cresol + NADH + H+ + O2
methylhydroquinone + nitrite + NAD+
show the reaction diagram
m-methoxyphenol + NADH + H+ + O2
methoxyhydroquinone + nitrite + NAD+
show the reaction diagram
m-nitrophenol + NADH + H+ + O2
4-nitrocatechol + nitrite + NAD+
show the reaction diagram
naphthalene + NADH + H+ + O2
(1R,2S)-cis-1,2-dihydroxynaphthalene + nitrite + NAD+
show the reaction diagram
naphthalene + O2
cis-1,2-dihydroxy-1,2-dihydronaphthalene
show the reaction diagram
o-cresol + NADH + H+ + O2
methylhydroquinone + 2-hydroxybenzyl alcohol + nitrite + NAD+
show the reaction diagram
Q5BM20 and Q6QUY4 and Q45695 and Q6QUY3
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mutant V350F produces methylhydroquinone at 1.52 nmol/min/mg of protein and 2-hydroxybenzyl alcohol at 0.74 nmol/min/mg of protein. Mutant V350M produces methylhydroquinone at 1.97 nmol/min/mg of protein and 2-hydroxybenzyl alcohol at 0.11 nmol/min/mg of protein
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?
o-methoxyphenol + NADH + H+ + O2
methoxyhydroquinone + nitrite + NAD+
show the reaction diagram
Q5BM20 and Q6QUY4 and Q45695 and Q6QUY3
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mutant V350F produces methoxyhydroquinone at 2.5 nmol/min/mg of protein. Mutant V350M produces methoxyhydroquinone at 2.4 mol/min/mg of protein
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?
o-nitrophenol + NADH + H+ + O2
nitrohydroquinone + 3-nitrocatechol + nitrite + NAD+
show the reaction diagram
Q5BM20 and Q6QUY4 and Q45695 and Q6QUY3
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product of wild-type. Mutant V350F produces both nitrohydroquinone at a rate of 0.75 nmol/min/mg of protein and 3-nitrocatechol at a rate of 0.069 nmol/min/mg of protein from o-nitrophenol. Mutant V350M produces both nitrohydroquinone at 0.33 nmol/min/mg of protein and 3-nitrocatechol at 0.089 nmol/min/mg of protein
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?
additional information
?
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
I204Y
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mutation in alpha subunit DntAc, results in two- to fourfold faster oxidization of the aminonitrotoluenes
V350F
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mutant displays significantly increased activity towards o-nitrophenol (47 times), m-nitrophenol (34 times), and o-methoxyphenol (174 times) as well as an expanded substrate range that now includes m-methoxyphenol, o-cresol, and m-cresol
V350M
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mutant displays increased activity towards o-nitrophenol (20 times) and o-methoxyphenol (162 times) as well as novel activity towards o-cresol
I204Y
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mutation in alpha subunit DntAc, results in two- to fourfold faster oxidization of the aminonitrotoluenes
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V350F
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mutant displays significantly increased activity towards o-nitrophenol (47 times), m-nitrophenol (34 times), and o-methoxyphenol (174 times) as well as an expanded substrate range that now includes m-methoxyphenol, o-cresol, and m-cresol
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V350M
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mutant displays increased activity towards o-nitrophenol (20 times) and o-methoxyphenol (162 times) as well as novel activity towards o-cresol
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additional information