Information on EC 1.13.11.37 - hydroxyquinol 1,2-dioxygenase

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

EC NUMBER
COMMENTARY hide
1.13.11.37
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RECOMMENDED NAME
GeneOntology No.
hydroxyquinol 1,2-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
benzene-1,2,4-triol + O2 = maleylacetate
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
2,4,5-trichlorophenoxyacetate degradation
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4-aminophenol degradation
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4-nitrophenol degradation II
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gamma-resorcylate degradation I
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gamma-resorcylate degradation II
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resorcinol degradation
Chlorocyclohexane and chlorobenzene degradation
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Benzoate degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
benzene-1,2,4-triol:oxygen 1,2-oxidoreductase (decyclizing)
An iron protein. Highly specific; catechol and pyrogallol are acted on at less than 1% of the rate at which hydroxyquinol is oxidized.
CAS REGISTRY NUMBER
COMMENTARY hide
91847-14-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
BA-5-17, grown in benzamide medium
SwissProt
Manually annotated by BRENDA team
grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
Azotobacter sp. GP1 / DSM 6428 / ATCC 49806
grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
AC1100, grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
L. ex Fr., 69346, grown with cellobiose
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Manually annotated by BRENDA team
Fomes pinicola
Sw. ex Fr., Karst. B.H., grown with cellobiose
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Manually annotated by BRENDA team
f. sp. vasinfectum
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Manually annotated by BRENDA team
Lenzites trabea
Pers. ex Fr., Fr. Karst. A-576, grown with cellobiose
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Manually annotated by BRENDA team
Polyporus dichrous
Fr., grown with cellulose
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Manually annotated by BRENDA team
Poria ambigua
Bres. BB3-1, grown with cellulose
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Manually annotated by BRENDA team
isolated from methyl parathion-polluted activated sludge, gene pdcC encoded in gene cluster pdcEDGFCBA
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Manually annotated by BRENDA team
gene pnpC
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Sporotrichum pulverulentum
grown in presence of vanillic acid
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Manually annotated by BRENDA team
strain 303 VKM AC-1284D, grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
strain 303 VKM AC-1284D, grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
Jacq. ex Fr., Karst. A-360, grown with cellulose
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
3-methylcatechol + O2
?
show the reaction diagram
4-chlorocatechol + O2
?
show the reaction diagram
6-chlorohydroxyquinol + O2
2-chloromaleylacetate
show the reaction diagram
benzene-1,2,4-triol + O2
3-hydroxy-cis,cis-muconate
show the reaction diagram
benzene-1,2,4-triol + O2
3-hydroxy-cis-cis-muconate
show the reaction diagram
benzene-1,2,4-triol + O2
maleylacetate
show the reaction diagram
catechol + O2
2-hydroxymuconic 6-semialdehyde
show the reaction diagram
extradiol ring cleavage
-
?
catechol + O2
?
show the reaction diagram
catechol + O2
cis,cis-muconate
show the reaction diagram
catechol + O2
cis,cis-muconic acid
show the reaction diagram
hydroxyquinol + O2
?
show the reaction diagram
hydroxyquinol + O2
maleylacetate
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
benzene-1,2,4-triol + O2
3-hydroxy-cis,cis-muconate
show the reaction diagram
benzene-1,2,4-triol + O2
3-hydroxy-cis-cis-muconate
show the reaction diagram
benzene-1,2,4-triol + O2
maleylacetate
show the reaction diagram
hydroxyquinol + O2
maleylacetate
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
stimulates at 0.2 mM
Cu2+
-
stimulates at 0.2 mM
Fe2+
-
stimulates at 0.2 mM
Mn2+
-
stimulates at 0.2 mM
Zn2+
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stimulates at 0.2 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4-Dichlorophenol
2,6-dichlorohydroquinone
3,4,6-trichlorocatechol
3,5-dichlorocatechol
3-chlorocatechol
3-methyl-5-chlorocatechol
4,5-dichlorocatechol
4-Chlorocatechol
catechol
EDTA
-
slight inhibition
monochlorohydroquinone
pyrogallol
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mixed inhibition
tetrachlorocatechol
tetrachlorohydroquinone
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Fe(NH4)2(SO4)2
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.06
6-chlorohydroxyquinol
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0.0012
Benzene-1,2,4-triol
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0.000035 - 0.02
Hydroxyquinol
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
72.3
6-chlorohydroxyquinol
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29
Benzene-1,2,4-triol
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6.35 - 11.4
Hydroxyquinol
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01274 - 0.01719
2,4-Dichlorophenol
0.00589 - 0.01094
2,6-dichlorohydroquinone
0.00536 - 0.0112
3,4,6-trichlorocatechol
0.0088 - 0.0169
3,5-dichlorocatechol
0.00698 - 0.03077
3-chlorocatechol
0.02732 - 0.0373
3-methyl-5-chlorocatechol
0.00585 - 0.0103
4,5-dichlorocatechol
0.0073 - 0.0526
4-Chlorocatechol
0.00956 - 10
catechol
0.00083 - 0.00107
monochlorohydroquinone
0.00069
pyrogallol
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0.00128 - 0.00349
tetrachlorocatechol
0.00226 - 0.01248
tetrachlorohydroquinone
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.37
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substrate hydroxyquinol
0.45
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substrate catechol
5.5
recombinant enzyme, crude enzyme extract, substrate 4-chlorocatechol, pH 7.5, 25C
7.06
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reactivated with 0.01 mM Fe2+
9.3
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purified recombinant His-tagged enzyme, pH 5.0, 45C
15.3
recombinant enzyme, crude enzyme extract, substrate hydroxyquinol, pH 7.5, 25C
284.6
51.7fold purified enzyme, with 4-chlorocatechol as substrate, at pH 7.5 and 25C; purified recombinant enzyme, substrate 4-chlorocatechol, pH 7.5, 25C
391
62.5fold purified enzyme, with catechol as substrate, at pH 7.5 and 25C; purified recombinant enzyme, substrate catechol , pH 7.5, 25C
479.5
purified recombinant enzyme, substrate 3-methylcatechol, pH 7.5, 25C
479.6
65.2fold purified enzyme, with 3-methylcatechol as substrate, at pH 7.5 and 25C
795.6
52fold purified enzyme, with hydroxyquinol as substrate, at pH 7.5 and 25C; purified recombinant enzyme, substrate hydroxyquinol, pH 7.5, 25C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
Sporotrichum pulverulentum
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enzyme assay
8.5
for catechol
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2 - 7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31000
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2 * 31000, SDS-PAGE
33000
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x * 33000, about, sequence calculation
33200
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x * 33200, deduced from nucleotide sequence
34250
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2 * 34250, SDS-PAGE
34800
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estimated from SDS-PAGE
38200
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alpha 1 * 39600 + beta 1 * 38200, SDS-PAGE
39600
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alpha 1 * 39600 + beta 1 * 38200, SDS-PAGE
58000
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gel filtration
61000
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gel filtration
68000
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gel filtration
79000
gel filtration
93000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
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alpha 1 * 39600 + beta 1 * 38200, SDS-PAGE
homodimer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor difffusion from a solution containing 2 M ammonium sulfate, 4% polyethylene glycol 400, 100 mM Hepes, pH 7.5, drops consist of 0.004 ml of 20 mg/ml protein solution and 0.006 ml reservoir solution equilibrated against 0.05 ml of reservoir solution, crystals diffract to 1.75 A
unit-cell dimensions: a = 81.15, b = 86.79, c = 114.93
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
activity not influenced after incubation for 10 min
55
60% activity loss after 10 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, no loss of activity after several weeks, at room temperature no considerable decrease after 1 day
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4C, loss of most of the activity after 1 week
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4C, reasonably stable for several weeks in the presence of isopropanol
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4C, stable for 2 to 3 weeks in elution buffer, can not be stored at 4C or frozen at -20C
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation and Ni-NTA column chromatography; recombinant His-tagged enzyme by nickel affinity chromatography and gel filtration by 51.7-65.2fold from Escherichia coli strain BL21(DE3)
Ni-NTA column chromatography
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recombinant 1,2-HQD
recombinant His-tagged enzyme 37.2fold from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cphA-1 from Arthrobacter chloropenolicus A6 is cloned into the vectro pCRT7/CT-TOPO, the construct is transformed into CL21(DE3)/pLysS cells.; cphA-2 from Arthrobacter chloropenolicus A6 is cloned into the vectro pCRT7/CT-TOPO, the construct is transformed into CL21(DE3)/pLysS cells.
expressed in Escherichia coli
expressed in Escherichia coli BL21 cells
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expressed in Escherichia coli BL21(DE3) cells; gene cphA-I, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
expression in Escherichia coli
expression in Escherichia coli BL21
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gene pnpC, DNA and amino acid sequence determination and analysis, expression of the His-tagged enzyme in Escherichia coli strain BL21(DE3)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
degradation
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