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Information on EC 1.14.13.64 - 4-hydroxybenzoate 1-hydroxylase
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EC Tree
1.14.13.64 4-hydroxybenzoate 1-hydroxylaseIUBMB Comments
Requires FAD. The enzyme from Candida parapsilosis is specific for 4-hydroxybenzoate derivatives and prefers NADH to NADPH as electron donor.
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Word Map
- 1.14.13.64
- parapsilosis
- hydroquinone
- phenol
- flavoprotein
-
fad-dependent
-
glucosyltransferase
- shikimate
- arbutin
- 3-hydroxybenzoate
-
6-hydroxylase
- 1,4-dihydroxybenzene
- synthesis
- gentisate
- pharmacology
The expected taxonomic range for this enzyme is: Saccharomycetales
Synonyms
4-hydroxybenzoate 1-hydroxylase, mnx1p, 4hb1h, 4-hydroxybenzoate 1-hydroxylase (decarboxylating), 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-hydroxybenzoate 1-hydroxylase
4-hydroxybenzoate 1-hydroxylase (decarboxylating)
4-hydroxybenzoate 1-monooxygenase
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4HB1H
Cp_4HB1H
FAD-dependent 4-hydroxybenzoate hydroxylase
MNX1
Mnx1p
Oxygenase, 4-hydroxybenzoate 1-mono
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PHBH
4-hydroxybenzoate 1-hydroxylase (decarboxylating)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
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4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
the conversion of 4-HB involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. It cannot be excluded that His230 activates 4-HB in 4HB1H for ipso-attack by the flavin C4a-hydroperoxide. Furthermore, it can also not be ruled out that the substrate of 4HB1H binds in a flipped orientation with the 4-hydroxyl moiety pointing towards the side chains of Tyr116 and His118
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4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
the conversion of 4-HB involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. It cannot be excluded that His230 activates 4-HB in 4HB1H for ipso-attack by the flavin C4a-hydroperoxide. Furthermore, it can also not be ruled out that the substrate of 4HB1H binds in a flipped orientation with the 4-hydroxyl moiety pointing towards the side chains of Tyr116 and His118
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxybenzoate,NAD(P)H:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
Requires FAD. The enzyme from Candida parapsilosis is specific for 4-hydroxybenzoate derivatives and prefers NADH to NADPH as electron donor.
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CAS REGISTRY NUMBER
COMMENTARY
134214-78-1
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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
2,4-dihydroxybenzoate + NADPH + O2
1,2,4-trihydroxybenzene + NADP+ + CO2
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-
-
?
2-fluoro-4-hydroxybenzoate + NADPH + O2
2-fluoro-1,4-dihydroxybenzene + NADP+ + CO2
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-
?
3,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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?
3,4-Dihydroxybenzoate + NADPH + O2
1,2,4-Trihydroxybenzene + NADP+ + CO2
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?
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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?
tetrafluoro-4-hydroxybenzoate + NAD(P)H + O2
2,3,5,6-tetrafluorohydroquinone + NAD(P)+ + CO2
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?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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-
-
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?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
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?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
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?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
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?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
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?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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?
4-Hydroxybenzoate + NAD(P)H + O2
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initial reaction of the catabolism of 4-hydroxybenzoate
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?
4-Hydroxybenzoate + NAD(P)H + O2
?
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the enzyme is induced when the yeast is grown on either 4-hydroxybenzoate, 2,3-dihydroxybenzoate, or 3,4-dihydroxybenzoate as the sole carbon source
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?
4-Hydroxybenzoate + NAD(P)H + O2
?
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initial reaction of the catabolism of 4-hydroxybenzoate
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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NADH is the preferred electron donor
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?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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NADH is the preferred electron donor
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?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
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the enzyme prefers NADH over NADPH as electron donor
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?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
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the enzyme prefers NADH over NADPH as electron donor
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?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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NADH is the preferred electron donor
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?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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NADH is the preferred electron donor
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?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
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the enzyme prefers NADH over NADPH as electron donor
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?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
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the enzyme prefers NADH over NADPH as electron donor
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?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
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?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
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?
additional information
?
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the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
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?
additional information
?
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the phenolate form of the substrates is important for catalysis and the substrate hydroxylation involvesthe electrophilic attack of the putative flavin hydroperoxide at the C1-atom of the aromatic ring
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?
additional information
?
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4HB1H catalyzes an oxidative decarboxylation reaction. 4HB1H is active with a wide range of 4-hydroxybenzoate (4-HB) derivatives. 4HB1H can also be induced by protocatechuate (PCA) and convert this compound directly into the central intermediate HHQ
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additional information
?
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4HB1H catalyzes an oxidative decarboxylation reaction. 4HB1H is active with a wide range of 4-hydroxybenzoate (4-HB) derivatives. 4HB1H can also be induced by protocatechuate (PCA) and convert this compound directly into the central intermediate HHQ
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additional information
?
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the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
-
-
?
additional information
?
-
-
the phenolate form of the substrates is important for catalysis and the substrate hydroxylation involvesthe electrophilic attack of the putative flavin hydroperoxide at the C1-atom of the aromatic ring
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-
?
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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
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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-
-
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?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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-
-
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?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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-
-
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?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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-
-
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?
4-Hydroxybenzoate + NAD(P)H + O2
?
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initial reaction of the catabolism of 4-hydroxybenzoate
-
-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
the enzyme is induced when the yeast is grown on either 4-hydroxybenzoate, 2,3-dihydroxybenzoate, or 3,4-dihydroxybenzoate as the sole carbon source
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-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
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initial reaction of the catabolism of 4-hydroxybenzoate
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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-
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?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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-
-
-
?
additional information
?
-
-
the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
-
-
?
additional information
?
-
-
the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
14
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purified recombinant enzyme, pH 7.6, 25°C, substrates 4-hydroxybenzoate and NADH
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION