Information on EC 1.13.11.1 - catechol 1,2-dioxygenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.13.11.1
-
RECOMMENDED NAME
GeneOntology No.
catechol 1,2-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
catechol + O2 = cis,cis-muconate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Benzoate degradation
-
-
catechol degradation to beta-ketoadipate
-
-
Chlorocyclohexane and chlorobenzene degradation
-
-
Fluorobenzoate degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
Toluene degradation
-
-
3-chlorocatechol degradation
-
-
phenol degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
catechol:oxygen 1,2-oxidoreductase
Requires Fe3+. Involved in the metabolism of nitro-aromatic compounds by a strain of Pseudomonas putida.
CAS REGISTRY NUMBER
COMMENTARY hide
9027-16-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ADP-96
-
-
Manually annotated by BRENDA team
used as a template for catechol 1,2-dioxygenase from Acinetobacter radioresistens strain S13
UniProt
Manually annotated by BRENDA team
gene catA
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain ATCC 19213
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-
Manually annotated by BRENDA team
strain TL3
-
-
Manually annotated by BRENDA team
strain TL3
-
-
Manually annotated by BRENDA team
ATCC 20184
-
-
Manually annotated by BRENDA team
HP 15
-
-
Manually annotated by BRENDA team
isolated from contaminated soil near Hangzhou Iron & Steel Group in China
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-
Manually annotated by BRENDA team
isolated from contaminated soil near Hangzhou Iron & Steel Group in China
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-
Manually annotated by BRENDA team
ATCC 13032
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-
Manually annotated by BRENDA team
strain JMP 134-1 is a spontaneous mutant of strain JMP 134, expressing the enzymes 2,4-D monooxygenase, chlorophenol hydroxylase, catechol 1,2-dioxygenase, dichloromuconate cycloisomerase, dienelactone hydrolase, and maleylacetate reductase constitutively
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Frateuria sp.
ANA-18
-
-
Manually annotated by BRENDA team
ANA-18
-
-
Manually annotated by BRENDA team
strain BI
-
-
Manually annotated by BRENDA team
strain BI
-
-
Manually annotated by BRENDA team
strain G27
-
-
Manually annotated by BRENDA team
strain G27
-
-
Manually annotated by BRENDA team
CC-MJ-2a
UniProt
Manually annotated by BRENDA team
DSM 43247
UniProt
Manually annotated by BRENDA team
DSM 44462
UniProt
Manually annotated by BRENDA team
DSM 44015
UniProt
Manually annotated by BRENDA team
DSM 44568
UniProt
Manually annotated by BRENDA team
DSM 44383
UniProt
Manually annotated by BRENDA team
DSM 43896
UniProt
Manually annotated by BRENDA team
DSM 43249
UniProt
Manually annotated by BRENDA team
DSM 44215
UniProt
Manually annotated by BRENDA team
NCIB 1053
-
-
Manually annotated by BRENDA team
Plesiomonas sp.
-
-
-
Manually annotated by BRENDA team
strain RW41
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-
Manually annotated by BRENDA team
KT 2440
-
-
Manually annotated by BRENDA team
strain isolated from the activated sludge samples of a sewage treatment plant at Bentwood Furniture Factory Jasienica, Poland, gene catA
UniProt
Manually annotated by BRENDA team
strain B 13
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-
Manually annotated by BRENDA team
strain B 13
-
-
Manually annotated by BRENDA team
Ba-0323
-
-
Manually annotated by BRENDA team
Ba-0323
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-
Manually annotated by BRENDA team
strain CC-BC11
UniProt
Manually annotated by BRENDA team
strain PA
-
-
Manually annotated by BRENDA team
strain PA
-
-
Manually annotated by BRENDA team
strain 135
-
-
Manually annotated by BRENDA team
strain 135
-
-
Manually annotated by BRENDA team
strain 89
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-
Manually annotated by BRENDA team
strain N75
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
YBL3
UniProt
Manually annotated by BRENDA team
WY 2-2
-
-
Manually annotated by BRENDA team
strain DSM 44343
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2,3-trihydroxybenzene + O2
2-hydroxymuconate
show the reaction diagram
-
-
-
-
?
2,3-dihydroxybenzoic acid + O2
?
show the reaction diagram
-
-
-
?
3,4,5,6-tetrachlorocatechol + O2
?
show the reaction diagram
-
-
-
?
3,4-dihydroxybenzoic acid + O2
?
show the reaction diagram
3,4-dimethylcatechol + O2
3,4-dimethyl-cis,cis-muconate
show the reaction diagram
3,5-dichlorocatechol + O2
(2E,4E)-2,4-dichlorohexa-2,4-dienedioate
show the reaction diagram
3,5-dichlorocatechol + O2
?
show the reaction diagram
-
-
-
?
3,5-dimethylcatechol + O2
3,5-dimethyl-cis,cis-muconate
show the reaction diagram
3-butylcatechol + O2
2-butylhexa-2,4-dienedioic acid
show the reaction diagram
-
weak activity
-
-
?
3-chloro-5-methylcatechol + O2
2-chloro-4-methylhexa-2,4-dienedioate
show the reaction diagram
3-chlorocatechol + O2
2-chloro-cis,cis-muconate
show the reaction diagram
3-chloropyrocatechol + O2
?
show the reaction diagram
3-ethylcatechol + O2
2-ethyl-cis,cis-muconic acid
show the reaction diagram
3-isopropylcatechol + O2
2-isopropyl-cis,cis-muconate
show the reaction diagram
3-methylcatechol + O2
(2Z,4Z)-2-methylhexa-2,4-dienedioate
show the reaction diagram
3-methylcatechol + O2
2-methyl-cis,cis-muconate
show the reaction diagram
3-methylcatechol + O2
3-methyl-cis,cis-muconate
show the reaction diagram
3-methylcatechol + O2
?
show the reaction diagram
3-methylpyrocatechol + O2
2,3,5-trimethyl-cis-cis-muconate
show the reaction diagram
3-methylthiocatechol + O2
2-methylthio-cis,cis-muconate
show the reaction diagram
-
very poor substrate
-
-
?
4,5-dichlorocatechol + O2
?
show the reaction diagram
4,5-difluorocatechol + O2
3,4-difluoro-cis-cis-muconate
show the reaction diagram
-
-
-
-
?
4-bromocatechol + O2
3-bromo-cis-cis-muconate
show the reaction diagram
4-chlorocatechol + O2
(2E,4Z)-3-chlorohexa-2,4-dienedioate
show the reaction diagram
4-chlorocatechol + O2
4-chloro-cis,cis-muconate
show the reaction diagram
-
-
-
-
?
4-chlorocatechol + O2
4-chlorocis,cis-muconate
show the reaction diagram
-
-
-
-
?
4-chlorocatechol + O2
?
show the reaction diagram
4-ethylcatechol + O2
4-ethyl-cis-cis-muconate
show the reaction diagram
-
42% of activity with catechol
-
-
?
4-fluorocatechol + O2
3-fluoro-cis,cis-muconate
show the reaction diagram
4-fluorocatechol + O2
4-fluoro-cis,cis-muconate
show the reaction diagram
-
65% of activity with catechol
-
-
?
4-hydroxybenzoic acid + O2
?
show the reaction diagram
4-iso-propylcatechol + O2
4-isopropyl-cis,cis-muconate
show the reaction diagram
-
23% of activity with catechol
-
-
?
4-methylcatechol + O2
(2Z,4Z)-3-methylhexa-2,4-dienedioate
show the reaction diagram
4-methylcatechol + O2
3-methyl-cis,cis-hexadienedioate
show the reaction diagram
-
-
-
?
4-methylcatechol + O2
3-methyl-cis,cis-muconate
show the reaction diagram
4-methylcatechol + O2
3-methylhexa-2,4-dienedioate
show the reaction diagram
4-methylcatechol + O2
4-methyl-cis,cis-muconate
show the reaction diagram
4-methylcatechol + O2
?
show the reaction diagram
4-methylpyrocatechol + O2
2,4,5-trimethyl-cis-cis-muconate
show the reaction diagram
4-n-propylcatechol + O2
4-n-propyl-cis,cis-muconate
show the reaction diagram
-
17% of activity with catechol
-
-
?
4-tert-butylcatechol + O2
?
show the reaction diagram
benzene-1,2,4-triol + O2
?
show the reaction diagram
benzoate + O2
?
show the reaction diagram
-
-
-
-
?
benzoic acid + O2
?
show the reaction diagram
-
-
-
?
catechol + ?
?
show the reaction diagram
catechol + O2
2-hydroxymuconic semialdehyde
show the reaction diagram
-
-
-
ir
catechol + O2
cis,cis-muconate
show the reaction diagram
catechol + O2
cis,cis-muconic acid
show the reaction diagram
catechol + O2
cis-cis muconate
show the reaction diagram
assay at pH 8.0, 30°C
-
-
?
hydroxyquinol + O2
?
show the reaction diagram
i.e. 1,2,4-trihydroxy benzene
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-
?
hydroxyquinol + O2
maleylacetic acid
show the reaction diagram
phenol + O2
?
show the reaction diagram
protocatechuate + O2
?
show the reaction diagram
i.e. 3,4-dihydroxybenzoate
-
-
?
pyrocatechol + O2
2,5-dimethyl-cis-cis-muconate
show the reaction diagram
pyrogallol + O2
alpha-hydroxymuconic acid
show the reaction diagram
tetrachlorocatechol + O2
cis,cis-tetrachloromuconic acid
show the reaction diagram
-
-
-
-
?
additional information
?
-
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
3,5-dichlorocatechol + O2
(2E,4E)-2,4-dichlorohexa-2,4-dienedioate
show the reaction diagram
3-chloro-5-methylcatechol + O2
2-chloro-4-methylhexa-2,4-dienedioate
show the reaction diagram
4-methylcatechol + O2
(2Z,4Z)-3-methylhexa-2,4-dienedioate
show the reaction diagram
A0F0B5, Q0VH42
-
-
-
?
4-methylcatechol + O2
3-methyl-cis,cis-hexadienedioate
show the reaction diagram
A0F0B5, Q0VH42
-
-
-
?
4-methylcatechol + O2
3-methylhexa-2,4-dienedioate
show the reaction diagram
catechol + O2
cis,cis-muconate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
-
1 mmol/l, 30°C, 15 min, 106% remaining activity
Ca2+
-
1 mmol/l, 30°C, 15 min, 168% remaining activity
Cd2+
-
activates by 127% at 3 mM
Fe
-
each subunit contained one iron
Ni2+
-
1 mmol/l, 30°C, 15 min, 74.6% remaining activity
Pb2+
-
1 mmol/l, 30°C, 15 min, 281% remaining activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
progressive inactivation, loss of all activation after 90 min, reactivation with Fe3+
1,2-naphthoquinone
-
-
2,2'-dipyridyl
complete inhibition at 2 mM, 99.9% at 1 mM
2,4-Dichlorophenol
26.0% inhibition at 0.1 mM, 29.8% at 0.3 mM
2-chlorophenol
31.1% inhibition at 0.1 mM, 17% at 0.3 mM
2-mercaptoethanol
2-Methylphenol
24.7% inhibition at 0.1 mM
3,4,5,6-tetrachlorocatechol
competitive inhibitor
3,4,5-trichlorocatechol
-
competitive inhibitor
3,5-dichlorocatechol
competitive inhibitor
3-Isopropylcatechol
-
-
3-methylcatechol
3-methylphenol
20.4% inhibition at 0.1 mM, 32% at 0.3 mM
3-methylthiocatechol
-
competitive inhibitor
4,5-dichlorocatechol
4-Chlorophenol
11% inhibition at 0.1 mM, 13% at 0.3 mM
4-Methylcatechol
4-Methylphenol
8% inhibition at 0.1 mM, 27.5% at 0.3 mM
4-nitrocatechol
AgNO3
alpha,alpha'-dipyridyl
-
94% inhibition, 1 mM
alpha-chloro-3,4-dihydroxyacetophenone
-
-
catechol
substrate inhibition at over 0.08 mM substrate concentration
CuCl2
-
0.1 mM, 41% inhibition
CuSO4
-
0.1 mM, 10 min, complete inhibition
dichlorocatechol
-
-
FeCl3
-
0.1 mM, 14% inhibition
FeSO4
-
0.1 mM, 10 min, 12% inhibition
gallic acid
-
-
glutathione
-
-
H2O2
-
0.1 mM, 10 min, 98% inhibition
HgCl2
Hydroxyquinol
-
-
iodoacetic acid
K+
-
1 mM, inhibits the free enzyme by 38%, no inhibition of the immobilized enzyme by K+
L-cysteine
-
-
mercaptoethanol
-
0.1 mM, 10 min, 98% inhibition
Mg2+
-
1 mM, inhibits the free enzyme by 9%, no inhibition of the immobilized enzyme by Mg2+
NH4+
-
10 mM, inhibits the immobilized enzyme by 40%, the free enzyme by 50%
o-benzoquinone
-
-
o-phenanthroline
p-benzoquinone
-
-
p-chloromercuribenzoate
p-hydroxymercuribenzoate
-
-
PbSO4
-
0.1 mM, 75% loss of activity
Phenanthroline
complete inhibition at 3 mM, 99% at 1 mM
pyrogallol
-
-
Sodium dithionite
-
1 mM, 36% loss of activity
streptomycin sulfate
-
5%, 10 min, 80% inhibition
tetrachlorocatechol
-
markedly inhibitory at concentration above 4 microM
Tiron
Vanillin
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Fe3+
Frateuria sp.
-
CD I and CD II respectively
sodium dodecyl benzene sulfonate
-
-
Tween 80
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.7
2,3-Dihydroxybenzoic acid
in 50 mM Tris/HCl, pH 7.2, 25°C
0.0007 - 0.002
3-chlorocatechol
0.0044
3-ethylcatechol
-
-
0.001 - 0.286
3-methylcatechol
0.0005
3-methylthiocatechol
-
-
0.02
4,5-difluorocatechol
-
-
0.3
4-bromocatechol
-
-
0.0001 - 0.2081
4-Chlorocatechol
0.0007 - 0.02
4-Fluorocatechol
0.0012 - 0.435
4-Methylcatechol
0.00025 - 0.11
catechol
0.097
Hydroxyquinol
in 50 mM Tris/HCl, pH 7.2, 25°C
0.06 - 0.1
oxygen
0.31
protocatechuate
in 50 mM Tris/HCl, pH 7.2, 25°C
0.0045
pyrogallol
in 50 mM Tris/HCl, pH 7.2, 25°C
0.0005
tetrachlorocatechol
-
-
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.28
2,3-Dihydroxybenzoic acid
Rhodococcus opacus
P95607
in 50 mM Tris/HCl, pH 7.2, 25°C
0.18
3-chlorocatechol
Rhodococcus opacus
P95607
in 50 mM Tris/HCl, pH 7.2, 25°C
0.4 - 10.62
3-methylcatechol
0.17 - 0.18
4,5-dichlorocatechol
0.4
4,5-difluorocatechol
Pseudomonas putida
-
rate dependent on the nucleophilic reactivity
0.63
4-bromocatechol
Pseudomonas putida
-
rate dependent on the nucleophilic reactivity
0.4
4-chloro-5-fluorocatechol
Pseudomonas putida
-
rate dependent on the nucleophilic reactivity
0.27 - 1.74
4-Chlorocatechol
3.4 - 4
4-Fluorocatechol
0.72 - 20.7
4-Methylcatechol
2 - 54
catechol
0.28
Hydroxyquinol
Rhodococcus opacus
P95607
in 50 mM Tris/HCl, pH 7.2, 25°C
0.04
protocatechuate
Rhodococcus opacus
P95607
in 50 mM Tris/HCl, pH 7.2, 25°C
2.41
pyrogallol
Rhodococcus opacus
P95607
in 50 mM Tris/HCl, pH 7.2, 25°C
kcat/KM VALUE [1/mMs-1]