Information on EC 1.14.13.31 - 2-nitrophenol 2-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.31
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RECOMMENDED NAME
GeneOntology No.
2-nitrophenol 2-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-nitrophenol + 2 NADPH + 2 H+ + O2 = catechol + nitrite + 2 NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-nitrophenol degradation
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SYSTEMATIC NAME
IUBMB Comments
2-nitrophenol,NADPH:oxygen 2-oxidoreductase (2-hydroxylating, nitrite-forming)
Involved in the metabolism of nitro-aromatic compounds by a strain of Pseudomonas putida.
CAS REGISTRY NUMBER
COMMENTARY hide
104520-84-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain NyZ215, gene onpA encoded in the onpABC operon
SwissProt
Manually annotated by BRENDA team
strain NyZ215, gene onpA encoded in the onpABC operon
SwissProt
Manually annotated by BRENDA team
strain JS905
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Manually annotated by BRENDA team
strain JS905
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Manually annotated by BRENDA team
strain B2
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-benzoquinone + NADPH + H+
catechol + NADP+
show the reaction diagram
2-nitrophenol + NADPH + H+ + O2
2-benzoquinone + NADP+ + H2O + nitrite
show the reaction diagram
2-nitrophenol + NADPH + H+ + O2
catechol + NADP+ + H2O + nitrite
show the reaction diagram
2-nitrophenol + NADPH + O2
3-nitrocatechol + NADP+ + H2O
show the reaction diagram
2-nitrophenol + NADPH + O2
?
show the reaction diagram
2-nitrophenol + NADPH + O2
catechol + nitrite + NADP+ + H2O
show the reaction diagram
3-methyl-2-nitrophenol + NADPH + O2
3-methylcatechol + NADP+ + H2O
show the reaction diagram
4-chloro-2-nitrophenol + NADPH + O2
4-chlorocatechol + NADP+ + H2O
show the reaction diagram
4-formyl-2-nitrophenol + NADPH + O2
4-formyl-1,2-benzenediol + NADP+ + H2O
show the reaction diagram
4-methyl-2-nitrophenol + NADPH + H+ + O2
4-methyl-catechol + NADP+ + H2O + nitrite
show the reaction diagram
4-methyl-2-nitrophenol + NADPH + O2
4-methylcatechol + NADP+ + H2O
show the reaction diagram
4-nitroresorcinol + NADPH + O2
?
show the reaction diagram
5-fluoro-2-nitrophenol + NADPH + H+ + O2
5-fluoro-catechol + NADP+ + H2O + nitrite
show the reaction diagram
about 20% of the activity with 2-nitrophenol
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-
?
5-methyl-2-nitrophenol + NADPH + O2
5-methylcatechol + NADP+ + H2O
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-nitrophenol + NADPH + H+ + O2
catechol + NADP+ + H2O + nitrite
show the reaction diagram
2-nitrophenol + NADPH + O2
?
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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30% stimulation at 4 mM
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4-dinitrophenol
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competitive inhibition
2-Nitrophenol
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substrate inhibition above 0.02 mM
N-ethylmaleimide
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80-90% inhibition at 0.008 mM per g protein, irreversible by dilution, inhibition does not affect enzyme activity, but retards translocation of the substrate into the cytoplasm
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.008
2-Nitrophenol
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0.14
NADPH
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0005
2,4-dinitrophenol
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
12
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with 4-chloro-2-nitrophenol as substrate
50
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with 4-methyl-2-nitrophenol as substrate
60
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with 2-nitrophenol as substrate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8
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o-nitrophenol, 4-chloro-2-nitrophenol
7.5
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assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 9
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pH 6.5: about 60% of activity maximum, pH 9.0: about 55% of activity maximum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
58000
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gel filtration
65000
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SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8
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highest stability
438883
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
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stable for several hours in 20 mM phosphate buffer or 50 mM Tris buffer
40
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2 min, complete inactivation in absence of o-nitrophenol, 2-nitrophenol above 0.2 mM prevents heat inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-nitrophenol stabilizes against heat inactivation
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glycerol stabilizes during storage at -20°C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 50% glycerol, less than 25% loss of activity after 5 days
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4°C, 20 mM phosphate buffer, 50 mM Tris buffer, pH 7.5, 4 mM DTT, less than 35% loss of activity after 5 days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
genes onpA and onpB, DNA and amino acid sequence determination and analysis, phylogenetic analysis, subcloning and expression in Escherichia coli, co-expression with onpB, but not of onpA alone, in the catechol utilizer Pseudomonas putida strain PaW340 confers the ability to grow on 2-nitrophenol