Information on EC 1.13.11.2 - catechol 2,3-dioxygenase

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

EC NUMBER
COMMENTARY hide
1.13.11.2
-
RECOMMENDED NAME
GeneOntology No.
catechol 2,3-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
catechol + O2 = 2-hydroxymuconate-6-semialdehyde
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-nitrotoluene degradation
-
-
Benzoate degradation
-
-
catechol degradation to 2-oxopent-4-enoate I
-
-
catechol degradation to 2-oxopent-4-enoate II
-
-
Chlorocyclohexane and chlorobenzene degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
phenol degradation
-
-
Styrene degradation
-
-
toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol)
-
-
toluene degradation to 2-oxopent-4-enoate I (via o-cresol)
-
-
Xylene degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
catechol:oxygen 2,3-oxidoreductase (decyclizing)
Requires FeII. The enzyme initiates the meta-cleavage pathway of catechol degradation.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-46-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain YAA, recombinantly expressed in Escherichia coli JM109
-
-
Manually annotated by BRENDA team
strain YAA, recombinantly expressed in Escherichia coli JM109
-
-
Manually annotated by BRENDA team
strain IS-46
UniProt
Manually annotated by BRENDA team
strain IS-46
UniProt
Manually annotated by BRENDA team
strain 0-1
-
-
Manually annotated by BRENDA team
glucose grown cells do not possess catechol 2,3-dioxygenase activity in appreciable quantity
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain G4
-
-
Manually annotated by BRENDA team
strain G4
-
-
Manually annotated by BRENDA team
JS765
-
-
Manually annotated by BRENDA team
strain 335
-
-
Manually annotated by BRENDA team
strain 335
-
-
Manually annotated by BRENDA team
epigeic earthworm used in vermicomposting processes. Comparing initial wet olive cake and wet olive cake inoculated with Eisenia fetida catechol dioxygenase activity is detected. The catechol-dioxygenase apppears to be due to high microbial activity, catechol-dioxygenase is only detected when a vermincomposting process takes place on the wet olive cake.
-
-
Manually annotated by BRENDA team
strain JM83
-
-
Manually annotated by BRENDA team
strain BR219
-
-
Manually annotated by BRENDA team
strain A2
-
-
Manually annotated by BRENDA team
strain A2
-
-
Manually annotated by BRENDA team
isolate A235
-
-
Manually annotated by BRENDA team
no activity in Pleurotus ostreatus
fungi, strain 3020 DSV7240
-
-
Manually annotated by BRENDA team
no activity in Pseudomonas aeruginosa
strain RW41
-
-
Manually annotated by BRENDA team
no activity in Pseudomonas aeruginosa RW41
strain RW41
-
-
Manually annotated by BRENDA team
no actvity in Fusarium sp.
strain BI, no catechol 2,3-dioxygenase is dectectable. Activity is measured by production of maleylpyruvate (increase in A375 nm) for catechol 2,3-dosygenase.
-
-
Manually annotated by BRENDA team
no actvity in Fusarium sp. BI
strain BI, no catechol 2,3-dioxygenase is dectectable. Activity is measured by production of maleylpyruvate (increase in A375 nm) for catechol 2,3-dosygenase.
-
-
Manually annotated by BRENDA team
isolated from the marine sediment, chromosomal-encoded gene nahH
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-
Manually annotated by BRENDA team
isolated from the marine sediment, chromosomal-encoded gene nahH
-
-
Manually annotated by BRENDA team
Planococcus sp.
ZD 4-3
-
-
Manually annotated by BRENDA team
strain CFS 215
-
-
Manually annotated by BRENDA team
strain Pmen PC1 - strain Pmen PC12 and Pmen PC19, all analysed stains contain catechol 2,3-dioxygenase genes
-
-
Manually annotated by BRENDA team
KT 2440
-
-
Manually annotated by BRENDA team
strain mt2
-
-
Manually annotated by BRENDA team
strain MT4, recombinantly expressed in Escherichia coli
SwissProt
Manually annotated by BRENDA team
PaW94
-
-
Manually annotated by BRENDA team
Pseudomonas putida PpG 1064
PpG 1064
-
-
Manually annotated by BRENDA team
Pseudomonas putida Ppu PC13
strain Ppu PC13 - Ppu PC16, Ppu PC30, Ppu PC35, Ppu PC36 and Ppu PC39 contain catechol 2,3-dioxygenase genes. The stains Ppu PC14-PC16 and Ppu PC30 do not contain catechol 2,3-dioxygenase genes
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
T-2
-
-
Manually annotated by BRENDA team
strain UCC2
SwissProt
Manually annotated by BRENDA team
Pseudomonas putida UWC1-pQM899
UWC1-pQM899
-
-
Manually annotated by BRENDA team
Pseudomonas sp. CGMCC2953
strain CGMCC2953
-
-
Manually annotated by BRENDA team
isolated from the marine sediment, plasmid-encoded gene nahH
UniProt
Manually annotated by BRENDA team
strain KB35B
-
-
Manually annotated by BRENDA team
strain KL28
Uniprot
Manually annotated by BRENDA team
strain ND6
-
-
Manually annotated by BRENDA team
OC1
-
-
Manually annotated by BRENDA team
strain phDV1
-
-
Manually annotated by BRENDA team
S-47
-
-
Manually annotated by BRENDA team
W31
-
-
Manually annotated by BRENDA team
strain ZJF08
-
-
Manually annotated by BRENDA team
amino acid sequence of nahH from Pseudomonas stutzeri NA1 shows 96% sequence identity with the catechol 2,3-dioxygenase gene from Pseudomonas putida strain H.; strain NA1. Absorption spectra and gas chromatography/mass spectrometry analyses of intermediate metabolites of salicylate or catechol degradation by a crude extract of Pseudomonas stutzeri NA1 reveals the presence of the meta-ring cleavage product 2-hydroxymuconate semialdehyde as a major constituent.
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-
Manually annotated by BRENDA team
strain PK01
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
strain PA, activity detected with 2-hydroxyboenzothiazole as growth substrate
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-
Manually annotated by BRENDA team
strain PA, activity detected with 2-hydroxyboenzothiazole as growth substrate
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-
Manually annotated by BRENDA team
strain CTM
-
-
Manually annotated by BRENDA team
strain CTM
-
-
Manually annotated by BRENDA team
strain DK17
-
-
Manually annotated by BRENDA team
strain DK17
-
-
Manually annotated by BRENDA team
enzyme subgroup I.2.B, hybrid enzymes with type I.2.A enzyme from Pseudomonas sp.
-
-
Manually annotated by BRENDA team
isolated from the marine sediment, chromosomal-encoded gene nahH
-
-
Manually annotated by BRENDA team
isolated from the marine sediment, chromosomal-encoded gene nahH
-
-
Manually annotated by BRENDA team
Variovorax sp.
strain isolated from a heavy metal-polluted soil
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-
Manually annotated by BRENDA team
strain isolated from a heavy metal-polluted soil
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
-
inactivation of TodE and the subsequent accumulation of 3-vinylcatechol results in toxicity and cell death
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
2,3-dihydroxybiphenyl + O2
?
show the reaction diagram
2,4-dichlorophenol + O2
?
show the reaction diagram
2-chlorophenol + O2
?
show the reaction diagram
2-methylphenol + O2
?
show the reaction diagram
3,4-dihydroxybenzoate + O2
?
show the reaction diagram
3,4-dimethylcatechol + O2
2-hydroxy-5-methyl-6-oxo-hepta-2,4-dienoate
show the reaction diagram
3,5-dichlorocatechol + O2
?
show the reaction diagram
3,5-dimethylcatechol + O2
2-hydroxy-3,5-dimethyl-6-oxohexa-2,4-dienoic acid
show the reaction diagram
3-chlorocatechol + O2
2-chloro-2-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
3-chlorocatechol + O2
3-chloro-2-hydroxymuconate semialdehyde
show the reaction diagram
3-formylcatechol + O2
3-formyl-2-hydroxymuconate semialdehyde
show the reaction diagram
-
-
-
?
3-hydroxycatechol + O2
3-hydroxymuconic acid
show the reaction diagram
3-methoxycatechol + O2
2-hydroxy-3-methoxy-6-oxohexa-2,4-dienoate
show the reaction diagram
-
-
-
-
?
3-methoxycatechol + O2
2-hydroxy-3-methoxymuconate semialdehyde
show the reaction diagram
3-methylcatechol + O2
2-hydroxy-3-methylmuconate semialdehyde
show the reaction diagram
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoate
show the reaction diagram
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoic acid
show the reaction diagram
3-methylcatechol + O2
?
show the reaction diagram
3-methylcatechol + O2
cis,cis-2-hydroxy-6-oxohepta-2,4-dienoate + H+
show the reaction diagram
3-methylphenol + O2
?
show the reaction diagram
3-phenylcatechol + O2
2-hydroxy-3-phenylmuconate semialdehyde
show the reaction diagram
-
-
-
?
3-sulfocatechol + O2 + H2O
(2E,4Z)-2-hydroxymuconate + bisulfite + H+
show the reaction diagram
-
-
-
-
?
3-vinylcatechol + O2
?
show the reaction diagram
-
-
-
-
?
4,5-dichlorocatechol + O2
?
show the reaction diagram
-
-
-
-
?
4-alkylcatechol + O2
?
show the reaction diagram
4-bromocatechol + O2
4-bromo-2-hydroxymuconate semialdehyde
show the reaction diagram
-
-
-
?
4-chlorocatechol + O2
4-chloro-2-hydroxymuconate
show the reaction diagram
-
-
-
?
4-chlorocatechol + O2
4-chloro-2-hydroxymuconate semialdehyde
show the reaction diagram
4-chlorocatechol + O2
5-chloro-2-hydroxymuconic semialdehyde
show the reaction diagram
4-chlorocatechol + O2
?
show the reaction diagram
4-chlorophenol + O2
?
show the reaction diagram
-
-
-
-
?
4-ethylcatechol + O2
4-ethyl-2-hydroxymuconate semialdehyde
show the reaction diagram
4-fluorocatechol + O2
3-fluoro-2-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
-
-
-
-
?
4-formylcatechol + O2
4-formyl-2-hydroxymuconate semialdehyde
show the reaction diagram
4-hydroxymethylcatechol + O2
2-hydroxy-4-hydroxymethylmuconate semialdehyde
show the reaction diagram
rapid inactivation of enzyme during turnover
-
-
?
4-methylcatechol + O2
2-hydroxy-3-methyl-6-oxohexa-2,4-dienoate
show the reaction diagram
4-methylcatechol + O2
2-hydroxy-4-methyl-6-oxohexa-2,4-dienoate
show the reaction diagram
4-methylcatechol + O2
2-hydroxy-4-methylmuconate semialdehyde
show the reaction diagram
4-methylcatechol + O2
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate + H+
show the reaction diagram
-
-
-
-
?
4-methylcatechol + O2
?
show the reaction diagram
4-Methylphenol + O2
?
show the reaction diagram
4-n-butylcatechol + O2
?
show the reaction diagram
activity is 1.85fold higher than with catechol
-
-
?
4-n-heptylcatechol + O2
?
show the reaction diagram
45% of the activity with catechol
-
-
?
4-n-hexylcatechol + O2
?
show the reaction diagram
53% of the activity with catechol
-
-
?
4-n-nonylcatechol + O2
?
show the reaction diagram
10% of the activity with catechol
-
-
?
4-nitrocatechol + O2
2-hydroxy-4-nitromuconate semialdehyde
show the reaction diagram
alkylcatechol + O2
?
show the reaction diagram
degradation of aromatic compounds
-
-
?
butanol + O2
?
show the reaction diagram
-
-
-
-
?
catechol + O2
2-hydroxymuconate semialdehyde
show the reaction diagram
catechol + O2
2-hydroxymuconate-6-semialdehyde
show the reaction diagram
catechol + O2
2-hydroxymuconic semialdehyde
show the reaction diagram
catechol + O2
?
show the reaction diagram
ethanol + O2
?
show the reaction diagram
-
-
-
-
?
hydroquinone + O2
?
show the reaction diagram
methanol + O2
?
show the reaction diagram
-
-
-
-
?
phenol + O2
2-hydroxymuconic semialdehyde
show the reaction diagram
phenol + O2
?
show the reaction diagram
propanol + O2
?
show the reaction diagram
-
-
-
-
?
protocatechualdehyde + O2
?
show the reaction diagram
protocatechuate + O2
?
show the reaction diagram
-
-
-
-
?
tetrachlorohydroquinone + O2
?
show the reaction diagram
-
immobilized enzyme, no activity with the free enzyme
-
-
?
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
2,4-dichlorophenol + O2
?
show the reaction diagram
2-chlorophenol + O2
?
show the reaction diagram
2-methylphenol + O2
?
show the reaction diagram
3-methylphenol + O2
?
show the reaction diagram
4-alkylcatechol + O2
?
show the reaction diagram
P17262
initial step of long-chain alkylphenol cleavage pathway
-
-
?
4-Methylphenol + O2
?
show the reaction diagram
alkylcatechol + O2
?
show the reaction diagram
Q83U22
degradation of aromatic compounds
-
-
?
catechol + O2
2-hydroxymuconate semialdehyde
show the reaction diagram
catechol + O2
2-hydroxymuconate-6-semialdehyde
show the reaction diagram
phenol + O2
?
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K+
-
included in assay medium
additional information
-
not: Co2+, Mn2+, Cu2+, Cr3+, Zn2+, Ni2+, Cd2+, Ca2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2R)-trans-1,2-cyclohexanediol
-
-
(1S,2S)-trans-1,2-cyclohexanediol
-
-
1-naphthoquinoline
-
-
2-butanone
-
-
2-chlorophenol
2-Fluorophenol
-
-
2-hydroxyacetophenone
-
-
2-hydroxybenzyl alkohol
-
-
2-methoxyphenol
-
-
2-Pentanone
-
-
3-chlorocatechol
3-fluorocatechol
-
in the presence of O2
3-methylcatechol
3-Pentanone
-
-
3-vinylcatechol
-
C23O activity (TodE) is almost completely abrogated by exposure to 0.2 mM 3-vinylcatechol
4-Chlorocatechol
4-Methyl-2-nitrophenol
-
-
4-Methylcatechol
8-hydroxyquinoline
-
weak
acetone
acetophenone
-
-
Benzoate
-
-
benzyl alkohol
-
-
catechol
Cd2+
Variovorax sp.
-
minimal inhibitory concentrations cadmium to Variovorax sp. 12S strain in different media, overview
diethyldicarbonate
-
-
hydrogen peroxide
0.1 M, complete inactivation
i-Propanol
-
-
m-fluorophenol
-
-
m-Hydroxybenzoate
-
-
m-Nitrophenol
-
-
m-phenanthroline
-
-
methanol
-
-
monoiodoacetate
-
weak
n-butanol
-
-
n-Pentanol
-
-
n-Propanol
-
-
NaN3
-
the immobilized enzyme is less sensitive compared to the free enzyme
nitrobenzene
-
-
o-aminophenol
-
-
o-fluorophenol
-
-
o-Nitrophenol
-
-
o-phenanthroline
p-chloromercuribenzoate
p-fluorophenol
-
-
p-nitrophenol
-
-
salicylate
-
-
t-butanol
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8-hydroxyquinoline
-
-
ascorbate
-
incubation of the purified enzyme (PheB) with Fe2+ and ascorbate increases its activity by approximately sevenfold
KCl
-
2 M, more than 2fold stimulation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00187
3,5-dichlorocatechol
-
-
0.0055 - 0.0738
3,5-dimethylcatechol
0.00204
3-methoxycatechol
-
-
0.001 - 0.06
3-methylcatechol
0.0009 - 0.0016
4-Chlorocatechol
0.0625
4-Fluorocatechol
-
-
0.00129 - 1.1
4-Methylcatechol
0.0065
4-n-butylcatechol
25C, pH 7.2
0.001 - 0.714
catechol
0.007 - 0.063
O2
0.0427
Phenol
Planococcus sp.
pH 7.5, 40C
0.0228
Protocatechualdehyde
-
-
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.23 - 2.65
3,5-dimethylcatechol
0.58 - 490
3-methylcatechol
17 - 45
4-Chlorocatechol
0.76 - 930
4-Methylcatechol
0.46 - 930
catechol
additional information
additional information
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
340 - 1400
3-methylcatechol
250 - 400
4-Methylcatechol
810 - 1300
catechol
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
34
(1R,2R)-trans-1,2-cyclohexanediol
-
-
43
(1S,2S)-trans-1,2-cyclohexanediol
-
-
0.00056
1-naphthoquinoline
-
-
0.35
2-butanone
-
-
0.52
2-chlorophenol
-
-
0.56
2-Fluorophenol
-
-