Information on EC 1.13.11.37 - hydroxyquinol 1,2-dioxygenase

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

EC NUMBER
COMMENTARY hide
1.13.11.37
-
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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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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-
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redox reaction
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-
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reduction
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-
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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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Benzoate degradation
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Chlorocyclohexane and chlorobenzene degradation
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gamma-resorcylate degradation I
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gamma-resorcylate degradation II
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Metabolic pathways
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Microbial metabolism in diverse environments
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resorcinol degradation
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
Arthrobacter chlorophenolicus
strain A6, DSM12829T
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-
Manually annotated by BRENDA team
Arthrobacter chlorophenolicus A6
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Swissprot
Manually annotated by BRENDA team
BA-5-17, grown in benzamide medium
SwissProt
Manually annotated by BRENDA team
Azotobacter sp.
strain GP1, DSM 6428, ATCC 49806, grown with 2,4,6-trichlorophenol
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-
Manually annotated by BRENDA team
Azotobacter sp. GP1
strain 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
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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
strain PDS-7
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-
Manually annotated by BRENDA team
strain SAO101
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Manually annotated by BRENDA team
strain SAO101
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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, grown with 2,4,6-trichlorophenol
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Manually annotated by BRENDA team
strain 303, 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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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-muconic acid
show the reaction diagram
hydroxyquinol + O2
?
show the reaction diagram
hydroxyquinol + O2
maleylacetate
show the reaction diagram
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intradiol ringcleavage
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-
?
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
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+
-
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
Azotobacter sp.
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slight inhibition
monochlorohydroquinone
pyrogallol
Azotobacter sp.
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mixed inhibition
tetrachlorocatechol
tetrachlorohydroquinone
Tiron
Azotobacter sp.
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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
Streptomyces rochei
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-
29
Benzene-1,2,4-triol
Pimelobacter simplex
Q5PXQ6
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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
Azotobacter sp.
-
-
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
7.06
Azotobacter sp.
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reactivated with 0.01 mM Fe2+
9.3
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purified recombinant His-tagged enzyme, pH 5.0, 45°C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
-
enzyme assay
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
34800
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estimated from SDS-PAGE
40000
Arthrobacter chlorophenolicus A6
recombinant CphA-1
42000
Arthrobacter chlorophenolicus A6
recombinant CphA-2
58000
Azotobacter sp.
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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
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
-80°C, no loss of activity after several weeks, at room temperature no considerable decrease after 1 day
Azotobacter sp.
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4°C, loss of most of the activity after 1 week
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4°C, reasonably stable for several weeks in the presence of isopropanol
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4°C, stable for 2 to 3 weeks in elution buffer, can not be stored at 4°C or frozen at -20°C
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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.
Arthrobacter chlorophenolicus A6
expressed in Escherichia coli
expressed in Escherichia coli BL21 cells
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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
Arthrobacter chlorophenolicus
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degradation of mixtures of phenolic compounds by Arthrobacter chlorophenolicus A6
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