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Information on EC 1.13.11.74 - 2-aminophenol 1,6-dioxygenase
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EC Tree
1.13.11.74 2-aminophenol 1,6-dioxygenaseIUBMB Comments
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 . 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 .
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Word Map
- 1.13.11.74
-
2-aminomuconic
- dioxygenases
- nitrobenzene
-
fission
-
extradiol
- 6-semialdehyde
- alpha-subunits
- protocatechuate
- beta-subunits
- comamonas
-
meta-cleavage
-
dioxygenation
-
suicide
-
catecholic
- pseudoalcaligenes
- 4-nitrocatechol
- homoprotocatechuate
- mutase
-
wastewater
- 4-oxalocrotonate
-
2-his-1-carboxylate
-
facial
-
nonhaem
- nitroreductase
-
alpha2beta2
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms
2-aminophenol 1,6-dioxygenase, amnba, 2-aminophenol-1,6-dioxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-aminophenol-1,6-dioxygenase
amnA
amnB
amnBA
APD
amnA
-
-
-
-
amnB
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-aminophenol + O2 = 2-aminomuconate 6-semialdehyde
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
,
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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].
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-amino-4,5-dimethylphenol + O2
?
-
1.3% activity compared to 2-aminophenol
-
-
?
2-amino-4,5-dimethylphenol + O2
?
-
1.3% activity compared to 2-aminophenol
-
-
?
2-amino-4-chlorophenol + O2
?
-
15% activity compared to 2-aminophenol
-
-
?
2-amino-4-chlorophenol + O2
?
-
15% activity compared to 2-aminophenol
-
-
?
2-amino-4-chlorophenol + O2
?
-
6.8% activity compared to 2-aminophenol
-
-
?
2-amino-4-chlorophenol + O2
?
-
6.8% activity compared to 2-aminophenol
-
-
?
2-amino-5-chlorophenol + O2
?
68% activity compared to 2-aminophenol
-
-
?
2-amino-5-chlorophenol + O2
?
68% activity compared to 2-aminophenol
-
-
?
2-amino-m-cresol + O2
?
-
1% activity compared to 2-aminophenol
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
100% activity
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
100% activity
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
O34137; O24680
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
100% activity
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
100% activity
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
O34137; O24680
-
-
-
?
6-amino-m-cresol + O2
?
-
25% activity compared to 2-aminophenol
-
-
?
catechol + O2
?
O34137; O24680
suicide substrate of 2-aminophenol 1,6-dioxygenase
-
-
?
catechol + O2
?
O34137; O24680
suicide substrate of 2-aminophenol 1,6-dioxygenase
-
-
?
protocatechuate + O2
?
33% activity compared to 2-aminophenol
-
-
?
protocatechuate + O2
?
33% activity compared to 2-aminophenol
-
-
?
additional information
?
-
5% activity with catechol
-
-
?
additional information
?
-
5% activity with catechol
-
-
?
additional information
?
-
-
3-methylcatechol, 4-methylcatechol, 3-chlorocatechol, 4-chlorocatechol, 1,2,3-trihydroxybenzene, 1,2,4-trihydroxybenzene, 4-aminoresorcinol, 2-amino-p-cresol, 2,3-dihydroxybenzoic acid, protocatechuate, 2-methoxyphenol, 4-amino-3-hydroxybenzoic acid, 3-amino-4-hydroxybenzoic acid, 3-hydroxyanthranilic acid, and 4-amino-m-cresol are no substrates
-
-
?
additional information
?
-
-
ternary iron(II)-2-aminophenolate complexes (TpPh,Me)FeII(2-amino-4-tert-butylphenolate) and (TpPh,Me)FeII(2-amino-4,6-di-tert-butylphenolate) closely mimic the active site structure of the enzyme and at the same time displays C-C cleavage activity
-
-
-
additional information
?
-
-
3-methylcatechol, 4-methylcatechol, 3-chlorocatechol, 4-chlorocatechol, 1,2,3-trihydroxybenzene, 1,2,4-trihydroxybenzene, 4-aminoresorcinol, 2-amino-p-cresol, 2,3-dihydroxybenzoic acid, protocatechuate, 2-methoxyphenol, 4-amino-3-hydroxybenzoic acid, 3-amino-4-hydroxybenzoic acid, 3-hydroxyanthranilic acid, and 4-amino-m-cresol are no substrates
-
-
?
additional information
?
-
-
ternary iron(II)-2-aminophenolate complexes (TpPh,Me)FeII(2-amino-4-tert-butylphenolate) and (TpPh,Me)FeII(2-amino-4,6-di-tert-butylphenolate) closely mimic the active site structure of the enzyme and at the same time displays C-C cleavage activity
-
-
-
additional information
?
-
-
no activity with phenol, o-, m-, or p-cresol, aniline, o-, m-, or p-aminobenzoic acid, o-, m-, or p-phenylenediamine, protocatechuic acid, 2,3-dihydroxybenzoic acid, 3-aminophenol, 4-aminophenol, 2-amino-4-isopropylphenol, 2-amino-tert-butylphenol, 3-aminophenazin-2-ol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 3-amino-4-hydroxybenzoic acid, or 4-amino-3-hydroxybenzoic acid, amidol and 3-hydroxyanthralinic acid
-
-
?
additional information
?
-
-
no activity with phenol, o-, m-, or p-cresol, aniline, o-, m-, or p-aminobenzoic acid, o-, m-, or p-phenylenediamine, protocatechuic acid, 2,3-dihydroxybenzoic acid, 3-aminophenol, 4-aminophenol, 2-amino-4-isopropylphenol, 2-amino-tert-butylphenol, 3-aminophenazin-2-ol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 3-amino-4-hydroxybenzoic acid, or 4-amino-3-hydroxybenzoic acid, amidol and 3-hydroxyanthralinic acid
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-amino-5-chlorophenol + O2
?
68% activity compared to 2-aminophenol
-
-
?
2-amino-5-chlorophenol + O2
?
68% activity compared to 2-aminophenol
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
100% activity
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
-
-
-
?
2-aminophenol + O2
2-aminomuconate 6-semialdehyde
100% activity
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-nitrocatechol
-
suicide inhibitor, the enzyme completely loses its activity towards 2-aminophenol after incubation with 4-nitrocatechol for 100 s
catechol
-
the enzyme completely loses its activity towards 2-aminophenol after incubation with catechol for 100 s
catechol
O34137; O24680
the activity of the enzyme is restored after removal of catechol and incubation with ascorbate and FeCl2
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00077
2-amino-5-chlorophenol
in 10 mM sodium phosphate buffer, at pH 8.0 and 22°C
0.00089
2-Aminophenol
in 10 mM sodium phosphate buffer, at pH 8.0 and 22°C
0.0171
2-Aminophenol
-
at pH 8.0, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.063
1,2,4-Trihydroxybenzene
-
pH and temperature not specified in the publication
0.0067
3-chlorocatechol
-
pH and temperature not specified in the publication
0.0054
3-fluorocatechol
-
pH and temperature not specified in the publication
0.0068
3-methylcatechol
-
pH and temperature not specified in the publication
0.0091
4-aminoresorcinol
-
pH and temperature not specified in the publication
0.0104
4-Chlorocatechol
-
pH and temperature not specified in the publication
0.0095
4-methylcatechol
-
pH and temperature not specified in the publication
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
subunit alpha and catalytic subunit beta
UniProt
brenda
subunit alpha and catalytic subunit beta
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A2T0AXS7_9CLOT
469
0
52793
TrEMBL
-
A0A1Q9NYX2_9ARCH
262
0
29591
TrEMBL
-
A0A143Y2U4_9FIRM
462
0
51547
TrEMBL
-