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Information on EC 1.13.11.66 - hydroquinone 1,2-dioxygenase
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1.13.11.66 hydroquinone 1,2-dioxygenaseIUBMB Comments
The enzyme is an extradiol-type dioxygenase, and is a member of the nonheme-iron(II)-dependent dioxygenase family. It catalyses the ring cleavage of a wide range of hydroquinone substrates to produce the corresponding 4-hydroxymuconic semialdehydes.
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Word Map
- 1.13.11.66
- semialdehyde
- sphingomonas
- para-nitrophenol
-
4-monooxygenase
- methylhydroquinone
-
fission
- maleylacetate
- heterotetramer
-
monooxygenation
-
catecholic
-
alkylphenols
- p-benzoquinone
- burkholderia
-
wastewater
- chlorohydroquinone
- fluorescens
- 1,4-benzoquinone
- 4-hydroxybenzoate
- sludge
-
ironii
-
sensu
-
cupin
- 2-chloro-4-nitrophenol
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms
pnpcd, hydroquinone dioxygenase, hydroquinone 1,2-dioxygenase, two-subunit hydroquinone 1,2-dioxygenase, pnpc2, pnpc1, pdcde, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
HQDO
hydroquinone 1,2-dioxygenase
hydroquinone dioxygenase
mnpC
PnpC1
PnpC2
ring-cleavage hydroquinone 1,2-dioxygenase
type II HQDO
YaiA
hydroquinone dioxygenase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzene-1,4-diol + O2 = (2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
-
benzene-1,4-diol + O2 = (2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
catalytic mechanism, overview
benzene-1,4-diol + O2 = (2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
catalytic mechanism, overview
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
benzene-1,4-diol:oxygen 1,2-oxidoreductase (decyclizing)
The enzyme is an extradiol-type dioxygenase, and is a member of the nonheme-iron(II)-dependent dioxygenase family. It catalyses the ring cleavage of a wide range of hydroquinone substrates to produce the corresponding 4-hydroxymuconic semialdehydes.
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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
2,6-dibromohydroquinone + O2
2-bromomaleylacetate + Br-
-
-
-
?
2,6-dichloro-p-hydroquinone + O2
2-chloromaleylacetate + Cl-
-
-
-
?
2,6-dichlorohydroquinone + O2
2-chloromaleylacetate + Cl-
complete conversion of substrate
-
-
?
2,6-dichlorohydroquinone + O2
?
-
-
0.5-0.6 equiv. of chloride is released during turnover of substrate
-
?
2,6-dimethylhydroquinone + O2
2-methylmaleylacetone + ?
-
-
-
?
2-chloro-6-methylhydroquinone
?
-
complete conversion of substrate, yields a mixture of 1,2- and 1,6-cleavage products. The two modes of cleavage have different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations
-
?
2-methoxyhydroquinone + O2
?
59% of the activity with hydroquinone
-
-
?
2-pentylhydroquinone + O2
?
19% of the activity with hydroquinone
-
-
?
2-propylhydroquinone + O2
?
23% of the activity with hydroquinone
-
-
?
2-tert-butylhydroquinone + O2
?
5% of the activity with hydroquinone
-
-
?
chlorohydroquinone + O2
?
-
70% of the activity with hydroquinone
-
-
?
methoxyhydroquinone + O2
?
-
50% of the activity with hydroquinone
-
-
?
2,3-difluorohydroquinone + O2
?
-
80% of the activity with hydroquinone
-
-
?
2,3-difluorohydroquinone + O2
?
-
80% of the activity with hydroquinone
-
-
?
2,5-difluorohydroquinone + O2
?
-
75% of the activity with hydroquinone
-
-
?
2,5-difluorohydroquinone + O2
?
-
75% of the activity with hydroquinone
-
-
?
2-(1-methyl1-octyl)-hydroquinone + O2
?
less than 2% of the activity with hydroquinone
-
-
?
2-(1-methyl1-octyl)-hydroquinone + O2
?
less than 2% of the activity with hydroquinone
-
-
?
2-chlorohydroquinone + O2
?
-
ring cleavage product is an acylchloride, which reacts with water to give maleylacetate
-
?
2-chlorohydroquinone + O2
?
29% of the activity with hydroquinone
-
-
?
2-chlorohydroquinone + O2
?
29% of the activity with hydroquinone
-
-
?
2-ethylhydroquinone + O2
?
83% of the activity with hydroquinone
-
-
?
2-ethylhydroquinone + O2
?
83% of the activity with hydroquinone
-
-
?
2-hexylhydroquinone + O2
?
less than 2% of the activity with hydroquinone
-
-
?
2-hexylhydroquinone + O2
?
less than 2% of the activity with hydroquinone
-
-
?
2-methylhydroquinone + O2
?
139% of the activity with hydroquinone
-
-
?
3,5-difluorohydroquinone + O2
?
-
90% of the activity with hydroquinone
-
-
?
3,5-difluorohydroquinone + O2
?
-
90% of the activity with hydroquinone
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
C1I210; C1I209
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
?
bromohydroquinone + O2
?
-
30% of the activity with hydroquinone
-
-
?
bromohydroquinone + O2
?
-
30% of the activity with hydroquinone
-
-
?
hydroquinone + O2
4-hydroxymuconic acid semialdehyde
-
-
-
?
hydroquinone + O2
4-hydroxymuconic acid semialdehyde
consumption of an equimolar amount of molecular oxygen
-
-
?
hydroquinone + O2
gamma-hydroxymuconic acid semialdehyde
-
-
-
?
hydroquinone + O2
gamma-hydroxymuconic acid semialdehyde
-
-
-
?
methylhydroquinone + O2
?
-
120% of the activity with hydroquinone
-
-
?
methylhydroquinone + O2
?
substrate binding structure, overview
-
-
?
methylhydroquinone + O2
?
substrate binding structure, overview
-
-
?
additional information
?
-
-
no substrate: hydroxyquinol, catechol, 2-aminophenol,4-aminophenol, protocatechuate, and gentisate
-
-
?
additional information
?
-
-
no substrate: hydroxyquinol, catechol, 2-aminophenol,4-aminophenol, protocatechuate, and gentisate
-
-
?
additional information
?
-
-
YaiA is a hydroquinone dioxygenase that converts hydroquinone putatively to 4-hydroxymuconic semialdehyde in an oxygen-consuming reaction. Hydroquinone and methylhydroquinone are both substrates of YaiA
-
-
?
additional information
?
-
-
2-methylhydroquinone is a slightly better substrate than unsubstituted hydroquinone
-
-
?
additional information
?
-
-
YaiA is a hydroquinone dioxygenase that converts hydroquinone putatively to 4-hydroxymuconic semialdehyde in an oxygen-consuming reaction. Hydroquinone and methylhydroquinone are both substrates of YaiA
-
-
?
additional information
?
-
-
2-methylhydroquinone is a slightly better substrate than unsubstituted hydroquinone
-
-
?
additional information
?
-
-
no substrate: tetrafluorohydroquinone, 1,2,4-trihydroxybenzene, gentisate, catechol, resorcinol, pyrogallol, and phenol
-
-
?
additional information
?
-
-
no substrate: tetrafluorohydroquinone, 1,2,4-trihydroxybenzene, gentisate, catechol, resorcinol, pyrogallol, and phenol
-
-
?
additional information
?
-
exhibits a high degree of substrate specificity for 2,6-disubstituted hydroquinones, with halogens greatly preferred at those positions. The asymmetric substrate 2-chloro-6-methylhydroquinone yields a mixture of 87% 1,2-cleavage and 13% 1,6-cleavage products with different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations. Monosubstituted hydroquinones show a limited amount of ring cleavage but rapidly inactivate the enzyme in an O2-dependent fashion, suggesting that oxidation of the Fe(II) may be the cause
-
-
?
additional information
?
-
no substrates: 2,5-dichloro-p-hydroquinone, 6-chlorohydroxyquinol, hydroxyquinol, 2-chloro-p-hydroquinone, catechol, and 4-fluorocatechol
-
-
?
additional information
?
-
enzyme cleaves aromatic rings with two hydroxyl groups ar para positions preferably. No substrate: catechol
-
-
?
additional information
?
-
enzyme catalyzes the ring fission of hydroquinone to 4-hydroxymuconic semialdehyde and the degradation of chlorinated and several alkylated hydroquinones
-
-
?
additional information
?
-
enzyme catalyzes the ring fission of hydroquinone to 4-hydroxymuconic semialdehyde and the degradation of chlorinated and several alkylated hydroquinones
-
-
?
additional information
?
-
-
enzyme catalyzes the ring fission of hydroquinone to 4-hydroxymuconic semialdehyde and the degradation of chlorinated and several alkylated hydroquinones
-
-
?
additional information
?
-
hydroquinone 1,2-dioxygenase, a Fe(II) ring cleaving dioxygenase from Sphingomonas sp. strain TTNP3, oxidizes a wide range of hydroquinones to the corresponding 4-hydroxymuconic semialdehydes
-
-
?
additional information
?
-
-
hydroquinone 1,2-dioxygenase, a Fe(II) ring cleaving dioxygenase from Sphingomonas sp. strain TTNP3, oxidizes a wide range of hydroquinones to the corresponding 4-hydroxymuconic semialdehydes
-
-
?
additional information
?
-
enzyme catalyzes the ring fission of hydroquinone to 4-hydroxymuconic semialdehyde and the degradation of chlorinated and several alkylated hydroquinones
-
-
?
additional information
?
-
enzyme catalyzes the ring fission of hydroquinone to 4-hydroxymuconic semialdehyde and the degradation of chlorinated and several alkylated hydroquinones
-
-
?
additional information
?
-
hydroquinone 1,2-dioxygenase, a Fe(II) ring cleaving dioxygenase from Sphingomonas sp. strain TTNP3, oxidizes a wide range of hydroquinones to the corresponding 4-hydroxymuconic semialdehydes
-
-
?
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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
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
C1I210; C1I209
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
?
benzene-1,4-diol + O2
(2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
-
-
-
?
additional information
?
-
-
YaiA is a hydroquinone dioxygenase that converts hydroquinone putatively to 4-hydroxymuconic semialdehyde in an oxygen-consuming reaction. Hydroquinone and methylhydroquinone are both substrates of YaiA
-
-
?
additional information
?
-
-
YaiA is a hydroquinone dioxygenase that converts hydroquinone putatively to 4-hydroxymuconic semialdehyde in an oxygen-consuming reaction. Hydroquinone and methylhydroquinone are both substrates of YaiA
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Iron
Manganese
-
preincubation in presence of 0.1 mM Fe2+ and 1 mM Mn2+ increases activity by 10fold
additional information
Fe2+
C1I210; C1I209
a Fe2+-dependent dioxygenase, selectively utilizes Fe2+for its catalytic reaction. Four residues of enzyme PnpD, His256, Asn258, Glu262, and His303, coordinate the iron ion
Fe2+
required for catalysis, each of the four beta subunits in the asymmetric unit of the enzyme crystal binds one Fe(II) ion. The iron ion in each beta subunit is coordinated to three protein residues, His258, Glu264, and His305 and a water molecule
Iron
-
preincubation in presence of 0.1 mM Fe2+ and 1 mM Mn2+ increases activity by 10fold
Iron
-
10fold activation by Fe2+, each subunit binds one molecule of 4-hydroxybenzoate and one molecule of iron
Iron
the residues ligating the Fe(II) are H11, H227, and E276
additional information
C1I210; C1I209
Fe3+, Mn2+, Co2+, Ni2+, Cu2+, and Cd2+ cannot substitute for Fe2+
additional information
-
Fe3+, Mn2+, Cu+, Cu2+ do not support enzyme activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3,4-dihydroxybenzoate
0.2 mM, 94% inhibition; 0.2 mM, 94% inhibition
4-coumaric acid
0.2 mM, 97% inhibition; 0.2 mM, 97% inhibition
Vanillyl alcohol
0.2 mM, 62% inhibition; 0.2 mM, 62% inhibition
4-hydroxybenzoate
0.2 mM, 46% inhibition; 0.2 mM, 46% inhibition
additional information
-
4-hydrobenzoate, the competitive inhibitor of the heterotetrameric HapCD hydroquinone dioxygenase of Pseudomonas fluorescens ACB, stabilizes the enzyme
-
additional information
-
weak or no inhibition: 2-hydroxy-, 3-hydroxy-, 2,3-dihydroxy-, 2,5-dihydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,4,5-trihydroxy-, 3-chloro-4-hydroxy-, tetrafluoro-4-hydroxy-, 3-amino-4-hydroxy-, 4-hydroxy-3-methoxy-, 4-amino- and methyl 4-hydroxybenzoate; 6-hydroxynicotinate, 4-hydroxypropiophenone, 4-hydroxymandelate, 4-hydroxyphenylglycine, 4-hydroxybenzenesulfonic acid, and 4-methyl-, 4-methoxy-, and 4-aminophenol
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
ligandation with 4-hydroxybenzoate prevents the enzyme from irreversible inactivation
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.255
hydroquinone
-
pH 7.4, temperature not specified in the publication
0.021
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
0.07
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
0.12
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
0.19
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
0.26
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.4
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
1.6
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
1.8
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
4.8
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.7
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
7
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.88
crude extract, substrate 2-chlorohydroquinone, pH 7.0, 37°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE