Information on EC 1.13.11.74 - 2-aminophenol 1,6-dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.74
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RECOMMENDED NAME
GeneOntology No.
2-aminophenol 1,6-dioxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-aminophenol + O2 = 2-aminomuconate 6-semialdehyde
show the reaction diagram
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-aminophenol degradation
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4-nitrotoluene degradation II
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Aminobenzoate degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
2-aminophenol:oxygen 1,6-oxidoreductase (decyclizing)
The enzyme, a member of the nonheme-iron(II)-dependent dioxygenase family, is an extradiol-type dioxygenase that utilizes a non-heme ferrous iron to cleave the aromatic ring at the meta position (relative to the hydroxyl substituent). The enzyme also has some activity with 2-amino-5-methylphenol and 2-amino-4-methylphenol [1]. The enzyme from the bacterium Comamonas testosteroni CNB-1 also has the activity of EC 1.13.11.76, 2-amino-5-chlorophenol 1,6-dioxygenase [2].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-amino-4,5-dimethylphenol + O2
?
show the reaction diagram
2-amino-4-chlorophenol + O2
?
show the reaction diagram
2-amino-5-chlorophenol + O2
?
show the reaction diagram
2-amino-m-cresol + O2
?
show the reaction diagram
2-amino-p-cresol + O2
?
show the reaction diagram
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
show the reaction diagram
6-amino-m-cresol + O2
?
show the reaction diagram
catechol + O2
?
show the reaction diagram
protocatechuate + O2
?
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-amino-5-chlorophenol + O2
?
show the reaction diagram
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2,3-Trihydroxybenzene
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complete inhibition at 0.05 mM
1,2,4-Trihydroxybenzene
2,2'-dipyridyl
2,3-Dihydroxybenzoic acid
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20% inhibition at 0.05 mM
2-amino-p-cresol
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90% inhibition at 0.05 mM
2-methoxyphenol
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30% inhibition at 0.05 mM
3-Amino-4-hydroxybenzoic acid
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20% inhibition at 0.05 mM
3-chlorocatechol
3-fluorocatechol
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noncompetitive inhibition
3-hydroxyanthranilic acid
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20% inhibition at 0.05 mM
3-methylcatechol
4-amino-3-hydroxybenzoic acid
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30% inhibition at 0.05 mM
4-amino-m-cresol
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10% inhibition at 0.05 mM
4-aminoresorcinol
4-Chlorocatechol
4-Methylcatechol
4-nitrocatechol
5,5'-dithiobis-(2-nitrobenzoic acid)
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complete inhibition at 0.5 mM
AgNO3
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6% residual activity at 0.5 mM
catechol
Cu2+
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2.9% residual activity at 2 mM
CuSO4
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complete inhibition at 0.1 mM
Fe2+
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57.4% residual activity at 2 mM
FeCl3
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complete inhibition at 0.5 mM
FeSO4(NH4)2SO4
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78% residual activity at 0.5 mM
HgCl2
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12% residual activity at 0.5 mM
iodoacetate
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40% residual activity at 0.5 mM
K3Fe(CN)6
MgSO4
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79% residual activity at 0.5 mM
MnCl2
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53% residual activity at 0.5 mM
Mo2+
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96% residual activity at 2 mM
N-ethylmaleimide
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83% residual activity at 0.5 mM
NaN3
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complete inhibition at 0.5 mM
nitrilotriacetic acid
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86% residual activity at 2 mM
o-phenanthroline
p-chloromercuribenzoic acid
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65% residual activity at 0.5 mM
protocatechuate
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20% inhibition at 0.05 mM
pyrogallol
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noncompetitive inhibition
Tiron
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complete inhibition at 0.5 mM
additional information
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not inhibited by FeSO4
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00077
2-amino-5-chlorophenol
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in 10 mM sodium phosphate buffer, at pH 8.0 and 22°C
0.00089 - 0.0467
2-Aminophenol
0.0775 - 0.71
O2
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
147
2-Aminophenol
Pseudomonas pseudoalcaligenes
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in 50 mM Tris (pH 8.0) at 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.063
1,2,4-Trihydroxybenzene
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pH and temperature not specified in the publication
0.0067
3-chlorocatechol
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pH and temperature not specified in the publication
0.0054
3-fluorocatechol
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pH and temperature not specified in the publication
0.0068
3-methylcatechol
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pH and temperature not specified in the publication
0.0091
4-aminoresorcinol
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pH and temperature not specified in the publication
0.0104
4-Chlorocatechol
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pH and temperature not specified in the publication
0.0095
4-Methylcatechol
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pH and temperature not specified in the publication
0.0104
catechol
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pH and temperature not specified in the publication
0.0084
pyrogallol
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pH and temperature not specified in the publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2
EDTA
Comamonas testosteroni
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in 10 mM sodium phosphate buffer, at pH 8.0 and 22°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1.5
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crude extract, in 50 mM Tris (pH 8.0) at 25°C
21.6
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purified enzyme, in 50 mM Tris (pH 8.0) at 25°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29000
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2 * 35000 + 2 * 29000, calculated from amino acid sequence
30000
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2 * 35000 + 2 * 30000, SDS-PAGE
32000
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2 * 40000 + 2 * 32000, SDS-PAGE
33000
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2 * 38000 + 2 * 33000, SDS-PAGE
38000
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2 * 38000 + 2 * 33000, SDS-PAGE
39000
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2 * 39000 + 2 * 35000, SDS-PAGE
40000
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2 * 40000 + 2 * 32000, SDS-PAGE
130000
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gel filtration
140000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
heterotetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
holoenzyme, with FeII and in complexes with the substrate 2-aminophenol and the suicide inhibitor 4-nitrocatechol, hanging drop vapor diffusion method, using 0.1 M sodium cacodylate pH 6.5, 25% (w/v) PEG 3350, 0.2 M sodium chloride
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in complex with (4Z,6Z)-3-iminooxepin-2(3H)-one, 2-aminomuconic 6-semialdehyde and 4-nitrocatechol, hanging drop vapor diffusion method, using 25% (w/v) PEG 3350, 0.2 mM sodium chloride, 0.1 M sodium cacodylate pH 6.5
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
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the enzyme loses 50% of its activity upon incubation at 60°C for 5 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dialysis against 50 mM MOPS (pH 7.3) containing ethanol (10% [v/v]) for 24 h abolishes 95% of the activity of 2-aminophenol 1,6-dioxygenase
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, purified enzyme in 50 mM MOPS at pH 7.3 in the presence of 10% (v/v) glycerol, several months, no loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
acetone precipitation, DE52-cellulose column chromatography, DEAE-cellulofine A-500 column chromatography, and gel filtration
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ammonium sulfate precipitation, Mono Q column chromatography, and Superdex 200 gel filtration
Q6J1Z5 and Q6J1Z6
ethanol precipitation, MonoQ column chromatography, and Sephacryl S-300 gel filtration
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partial purification
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
O34137 and O24680
expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli DH5alpha cells
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expressed in Escherichia coli JM109 cells
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expressed in Escherichia coli XL-1 Blue cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E251A
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inactive
H13A
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inactive
H195Q
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inactive
H62A
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inactive
Y129F
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inactive
E251A
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inactive
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H13A
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inactive
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H195Q
-
inactive
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H62A
-
inactive
-
Y129F
-
inactive
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