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Information on EC 1.14.13.116 - geranylhydroquinone 3''-hydroxylase Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The expected taxonomic range for this enzyme is: Lithospermum erythrorhizon
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geranylhydroquinone 3''-hydroxylase
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geranylhydroquinone + NADPH + H+ + O2 = 3''-hydroxygeranylhydroquinone + NADP+ + H2O
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Biosynthesis of secondary metabolites
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shikonin biosynthesis
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Ubiquinone and other terpenoid-quinone biosynthesis
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geranylhydroquinone,NADPH:oxygen oxidoreductase (3''-hydroxylating)
Contains cytochrome P-450.
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Sieb. et Zucc.
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brenda
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geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
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likely to be involved in shikonin and dihydroechinofuran biosynthesis
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geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
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hydroxylation takes place specifically at position 3'', i.e. at the methyl group involved in the cyclization reaction. The reaction velocity obtained with 3-geranyl-4-hydroxybenzoic acid is more than 100 times lower than that obtained with geranylhydro-quinone
proton/proton correlation spectroscopic and proton/proton long-range correlation spectroscopic studies confirm that hydroxylation takes place specifically at position 3''
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geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
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likely to be involved in shikonin and dihydroechinofuran biosynthesis
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NADPH
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required, could not be replaced by NADH, FAD or FMN. The optimal concentration of NADPH for this reaction is between 1 and 5 mM
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Ancymidol
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1 mM, 38% inhibition
CO
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inhibitory effect of CO is reversed by illumination
cytochrome c
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0.01 mM, 96% inhibition
ketoconazole
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1 mM, 62% inhibition
Metyrapone
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1 mM, 14% inhibition
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cytochrome P-450
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involved in activity
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0.0015
geranylhydroquinone
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pH 7.4, 30°C, microsomal fraction
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7.4
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activity in K-phosphate buffer at pH 7.4 is only 40% of that observed in Tris-HCl buffer
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6.7 - 8.3
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50% of maximal activiyt at pH 6.7 and pH 8.3. Tris-Cl buffer
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brenda
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brenda
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addition of glycerol (20%, v/v) to the microsomal fraction before freezing results in the loss of 80% of the activity
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stable against freezing
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-70°C, 1 month, microsomal protein retains 82% of the original activity
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Yamamoto. H.; Inoue, K.; Li, S.M.; Heide, L.
Geranylhydroquinone 3'-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures
Planta
210
312-317
2000
Lithospermum erythrorhizon
brenda
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