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2,3,5,6-Tetrafluoro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
2,3,5,6-Tetrafluoro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
2,4-dihydroxybenzoate + NADPH + O2
1,2,4-trihydroxybenzene + NADP+ + CO2
-
-
-
?
2,5-Difluoro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
2,5-Difluoro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
2,6-Difluoro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
2,6-Difluoro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
2-chloro-4-hydroxybenzoate + NADH + O2
?
2-Chloro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
2-fluoro-4-hydroxybenzoate + NADPH + O2
2-fluoro-1,4-dihydroxybenzene + NADP+ + CO2
-
-
-
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
3,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
-
-
-
?
3,4-Dihydroxybenzoate + NADPH + O2
1,2,4-Trihydroxybenzene + NADP+ + CO2
-
-
-
?
3,5-Difluoro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
3,5-Difluoro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
3-Amino-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
3-Amino-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
3-Chloro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
3-Chloro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
3-Fluoro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
3-Fluoro-4-hydroxybenzoate + NADPH + O2
?
-
-
-
-
?
4-Hydroxy-3-methoxybenzoate + NADH + O2
?
-
-
-
-
?
4-Hydroxy-3-methoxybenzoate + NADPH + O2
?
-
-
-
-
?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
4-Hydroxy-3-nitrobenzoate + NADH + O2
?
-
-
-
-
?
4-Hydroxy-3-nitrobenzoate + NADPH + O2
?
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
4-Hydroxybenzoate + NAD(P)H + O2
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
protocatechuate + NAD(P)H + H+ + O2
?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
tetrafluoro-4-hydroxybenzoate + NAD(P)H + O2
2,3,5,6-tetrafluorohydroquinone + NAD(P)+ + CO2
-
-
-
-
?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
additional information
?
-
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
-
-
-
?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
-
-
-
?
2-chloro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
2-chloro-4-hydroxybenzoate + NADH + O2
?
-
-
-
-
?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
-
-
-
?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
-
-
-
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
-
-
-
-
?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
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
-
-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
initial reaction of the catabolism of 4-hydroxybenzoate
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
-
-
-
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
-
NADH is the preferred electron donor
-
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
-
-
-
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
-
NADH is the preferred electron donor
-
?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
-
the enzyme prefers NADH over NADPH as electron donor
-
-
?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
-
the enzyme prefers NADH over NADPH as electron donor
-
-
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
-
-
-
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
-
NADH is the preferred electron donor
-
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
-
-
-
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
-
NADH is the preferred electron donor
-
?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
-
the enzyme prefers NADH over NADPH as electron donor
-
-
?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
-
the enzyme prefers NADH over NADPH as electron donor
-
-
?
protocatechuate + NAD(P)H + H+ + O2
?
-
-
-
-
?
protocatechuate + NAD(P)H + H+ + O2
?
-
-
-
-
?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
-
-
-
-
?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
-
-
-
-
?
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 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
-
-
?
additional information
?
-
-
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
-
-
-
additional information
?
-
-
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
-
-
-
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 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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2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
4-Hydroxybenzoate + NAD(P)H + O2
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
protocatechuate + NAD(P)H + H+ + O2
?
additional information
?
-
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
-
-
-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
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
-
-
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
initial reaction of the catabolism of 4-hydroxybenzoate
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
-
-
-
?
protocatechuate + NAD(P)H + H+ + O2
?
-
-
-
-
?
protocatechuate + NAD(P)H + H+ + O2
?
-
-
-
-
?
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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evolution
-
phylogenetic analysis of FAD-dependent 4-hydroxybenzoate hydroxylases and 3-hydroxybenzoate 4-hydroxylase, phylogenetic analysis and tree, overview. Enzyme 4HB1H is only present in a small group of Saccharomycetes. Many FAD-binding proteins with unknown function in pezizomycetes and agaricomycetes have structural features in common with 4HB1H, but lack its C-terminal tail. 4HB1H belongs to a subgroup of structurally related group A FPMOs that catalyze para-hydroxylation reactions
evolution
-
phylogenetic analysis of FAD-dependent 4-hydroxybenzoate hydroxylases and 3-hydroxybenzoate 4-hydroxylase, phylogenetic analysis and tree, overview. Enzyme 4HB1H is only present in a small group of Saccharomycetes. Many FAD-binding proteins with unknown function in pezizomycetes and agaricomycetes have structural features in common with 4HB1H, but lack its C-terminal tail. 4HB1H belongs to a subgroup of structurally related group A FPMOs that catalyze para-hydroxylation reactions
-
metabolism
-
the enzyme is important in lignin degradation. The conversion of 4-hydroxybenzoate (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. The second step of the catabolism of 4-HB in Candida parapsilosis catalyzed by the homodimeric hydroquinone hydroxylase, HQH
metabolism
-
the enzyme is important in lignin degradation. The conversion of 4-hydroxybenzoate (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. The second step of the catabolism of 4-HB in Candida parapsilosis catalyzed by the homodimeric hydroquinone hydroxylase, HQH
-
physiological function
-
overexpression of the enzyme increases the tolerance of Candida parapsilosis cells to the antifungal drug terbinafine
physiological function
-
4-hydroxybenzoate 1-hydroxylase (4HB1H) from yeast catalyzes an oxidative decarboxylation reaction and is structurally similar to 3-hydroxybenzoate 6-hydroxylase (3HB6H), salicylate hydroxylase (SALH) and 6-hydroxynicotinate 3-monooxygenase (6HNMO). Genome mining suggests that the 4HB1H activity is widespread in the fungal kingdom and might be responsible for the oxidative decarboxylation of vanillate, an import intermediate in lignin degradation
physiological function
-
overexpression of the enzyme increases the tolerance of Candida parapsilosis cells to the antifungal drug terbinafine
-
physiological function
-
4-hydroxybenzoate 1-hydroxylase (4HB1H) from yeast catalyzes an oxidative decarboxylation reaction and is structurally similar to 3-hydroxybenzoate 6-hydroxylase (3HB6H), salicylate hydroxylase (SALH) and 6-hydroxynicotinate 3-monooxygenase (6HNMO). Genome mining suggests that the 4HB1H activity is widespread in the fungal kingdom and might be responsible for the oxidative decarboxylation of vanillate, an import intermediate in lignin degradation
-
additional information
-
structure comparisons and protein homology modelling, generation of a model of Candida parapsilosis Cp_HQH and models for Cp_4HB1H, Fusarium oxysporum Fo_4HB1H-like, and Boreostereum vibrans Bv_VibMO1 using Cutaneotrichosporon cutaneum Tc_PHHY (PDB ID 1pn0), Rhodococcus jostii Rj_3HB6H (PDB ID 4bk1) and Pseudomonas putida Pp_SALH (PDB ID 5evy) as template structures, overview
additional information
-
structure comparisons and protein homology modelling, generation of a model of Candida parapsilosis Cp_HQH and models for Cp_4HB1H, Fusarium oxysporum Fo_4HB1H-like, and Boreostereum vibrans Bv_VibMO1 using Cutaneotrichosporon cutaneum Tc_PHHY (PDB ID 1pn0), Rhodococcus jostii Rj_3HB6H (PDB ID 4bk1) and Pseudomonas putida Pp_SALH (PDB ID 5evy) as template structures, overview
-
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van Berkel, W.J.H.; Eppink, M.H.M.; Middelhoven, W.J.; Vervoort, J.; Rietjens, I.M.C.M.
Catabolism of 4-hydroxybenzoate in Candida parapsilosis proceeds through initial oxidative decarboxylation by a FAD-dependent 4-hydroxybenzoate 1-hydroxylase
FEMS Microbiol. Lett.
121
207-216
1994
Candida parapsilosis, Candida parapsilosis CBS604
brenda
Eppink, M.H.M.; Boeren, S.A.; Vervoort, J.; van Berkel, W.J.H.
Purification and properties of 4-hydroxybenzoate 1-hydroxylase (decarboxylating), a novel flavin adenine dinucleotide-dependent monooxygenase from Candida parapsilosis CBS604
J. Bacteriol.
179
6680-6687
1997
Candida parapsilosis, Candida parapsilosis CBS604
brenda
Moonen, M.J.H.; Fraaije, M.W.; Rietjens, I.M.C.M.; Laane, C.; Van Berkel, W.J.H.
Flavoenzyme-catalyzed oxygenations and oxidations of phenolic compounds
Adv. Synth. Catal.
344
1023-1035
2002
Candida parapsilosis, Candida parapsilosis CBS604
-
brenda
Holesova, Z.; Jakubkova, M.; Zavadiakova, I.; Zeman, I.; Tomaska, L.; Nosek, J.
Gentisate and 3-oxoadipate pathways in the yeast Candida parapsilosis: identification and functional analysis of the genes coding for 3-hydroxybenzoate 6-hydroxylase and 4-hydroxybenzoate 1-hydroxylase
Microbiology
157
2152-2163
2011
Candida parapsilosis
brenda
Shen, X.; Wang, J.; Wang, J.; Chen, Z.; Yuan, Q.; Yan, Y.
High-level de novo biosynthesis of arbutin in engineered Escherichia coli
Metab. Eng.
42
52-58
2017
Candida parapsilosis, Candida parapsilosis (G8B709), Candida parapsilosis CBS604, Candida parapsilosis CBS604 (G8B709)
brenda
Westphal, A.H.; Tischler, D.; van Berkel, W.J.H.
Natural diversity of FAD-dependent 4-hydroxybenzoate hydroxylases
Arch. Biochem. Biophys.
702
108820
2021
Candida parapsilosis, Candida parapsilosis CBS604
brenda
Shang, Y.; Wei, W.; Zhang, P.; Ye, B.C.
Engineering Yarrowia lipolytica for enhanced production of arbutin
J. Agric. Food Chem.
68
1364-1372
2020
Yarrowia lipolytica
brenda