1.1.3.38: vanillyl-alcohol oxidase
This is an abbreviated version!
For detailed information about vanillyl-alcohol oxidase, go to the full flat file.
Word Map on EC 1.1.3.38
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1.1.3.38
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opacification
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simplicissimum
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ostium
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veratryl
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flavinylation
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vertebrobasilar
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aphakia
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p-quinone
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logmar
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argan
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4-ethylphenol
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4-alkylphenols
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synthesis
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analysis
- 1.1.3.38
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opacification
- simplicissimum
-
ostium
-
veratryl
-
flavinylation
-
vertebrobasilar
- aphakia
- p-quinone
-
logmar
-
argan
- 4-ethylphenol
- 4-alkylphenols
- synthesis
- analysis
Reaction
Synonyms
4-allylphenol oxidase, 4-hydroxy-2-methoxybenzyl alcohol oxidase, Aryl-alcohol oxidase, EUGO, HMFO, Oxidase, vanillyl alcohol, RHA1_ro03282, vanillyl-alcohol oxidase, VAO, VAOA
ECTree
1.1.3.38 vanillyl-alcohol oxidaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.1.3.38 - vanillyl-alcohol oxidase
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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
3-methoxy-4-hydroxybenzyl alcohol + O2
3-methoxy-4-hydroxybenzaldehyde + H2O2
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i.e. vanillyl alcohol
i.e. vanillin
-
?
4-(3'-methylcrotyl)phenol + O2
4-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]phenol + 4-[(1E)-3-methylbuta-1,3-dien-1-yl]phenol
4-butylphenol + O2
4-but-1-en-1-ylphenol + 4-[(1R)-1-hydroxybutyl]phenol
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-
mutant D170E: 0% alcohol + 100% alkene. Mutant D170S: 82% alcohol + 18% alkene
-
?
4-cyclopentylphenol + O2
4-(1-cyclopenten-1-yl)phenol
-
-
-
?
4-ethylphenol + O2 + H2O
(R)-1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + H2O2
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-
product formed by wild-type enzyme and mutant enzyme D170S. The hydroxylation reaction in D170S is nearly completely blocked and this mutant converts short-chain alkylphenols to the corresponding alkenes. Mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 92% alcohol + 8% alkene
-
?
4-ethylphenol + O2 + H2O
(S)-1-(4'-hydroxyphenyl)ethanol + H2O2
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predominant product of mutant D170S/T457E
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ir
4-ethylphenol + O2 + H2O
1-(4'-hydroxyphenyl)ethanol + H2O2
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-
-
?
4-hydroxy-3-methoxybenzylamine + O2 + H2O
vanillin + H2O2 + NH3
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i.e. vanillylamine
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-
?
4-hydroxy-3-methoxyphenylglycol + O2 + H2O
2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one + H2O2
-
-
-
-
?
4-hydroxybenzyl alcohol + O2
4-hydroxybenzaldehyde + H2O2
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at 75% of the activity with vanillyl alcohol
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?
4-isopropylphenol + O2
4-(2-hydroxypropan-2-yl)phenol + 4-isopropenylphenol
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-
20% 4-hydroxyphenylalcohol + 80% 4-hydroxyphenylalkene
?
4-isopropylphenol + O2
4-isopropenylphenol + ?
-
-
mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 80% alcohol + 20% alkene
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?
4-Methylphenol + O2
?
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transient intermediate: p-quinone methide of the aromatic substrate in complex with reduced enzyme. Ordered sequential binding mechanism in which the rate of flavin reduction determines the turnover rate while the reduced enzyme-p-quinone methide binary complex rapidly reacts with dioxygen
-
-
?
4-n-butylphenol + O2
4-[(1E)-but-1-en-1-yl]phenol + 4-[(1Z)-but-1-en-1-yl]phenol
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-
93% cis-4-hydroxyphenylalkene + 7% trans-4-hydroxyphenylalkene
?
4-n-heptylphenol + O2
4-[(1E)-hept-1-en-1-yl]phenol + 4-[(1Z)-hept-1-en-1-yl]phenol
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-
50% cis-4-hydroxyphenylalkene + 50% trans-4-hydroxyphenylalkene
?
4-n-pentylphenol + O2
4-[(1E)-pent-1-en-1-yl]phenol + 4-[(1Z)-pent-1-en-1-yl]phenol + H2O2
4-n-propylphenol + O2
1-(4'-hydroxyphenyl)propanol + 4-(prop-1-en-1-yl)phenol
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-
mutant D170E: 7% alcohol + 93% alkene. Mutant D170S: 96% alcohol + 4% alkene
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?
4-propylphenol + O2
(R)-1-(4'-hydroxyphenyl)propanol + cis-1-(4'-hydroxyphenyl)propene + trans-1-(4'-hydroxyphenyl)propene
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-
in an aqueous medium the enzyme produces mainly (R)-1-(4'-hydroxyphenyl)propanol and low but equal amounts of cis-1-(4'-hydroxyphenyl)propene and trans-1-(4'-hydroxyphenyl)propene. In acetonitrile or toluene the concentration of the alcohol product decreases and the concentration of the cis-alkene product, but not the trans-alkene product increases
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?
4-Propylphenol + O2
1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
4-sec-butylphenol + O2
4-(2-hydroxybutan-2-yl)phenol + 4-(but-1-en-2-yl)phenol + 4-[(2Z)-but-2-en-2-yl]phenol
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-
26% 4-hydroxyphenylalcohol + 74% 4-hydroxyphenylalkene. 100% cis-4-hydroxyphenylalkene
?
4-sec-butylphenol + O2
?
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-
mutant D170E: 1% alcohol + 99% alkene. Mutant D170S: 78% alcohol + 22% alkene
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?
5,6,7,8-tetrahydro-2-naphthol + O2
?
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-
4% 4-hydroxyphenylalcohol + 94% 4-hydroxyphenylalkene + 2% 4-hydroxyphenylalkanone
?
5-indanol + O2
?
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-
16% 4-hydroxyphenylalcohol + 24% 4-hydroxyphenylalkene + 60% 4-hydroxyphenylalkanone
?
creosol + O2
vanillin + ?
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the conversion of cresol proceeds via a two-step enzymatic process. In the first step creosol is hydroxylated to yield vanillyl alcohol, and in the second step vanillyl alcohol is oxidized to yield vanillin
-
-
?
vanillyl alcohol + phenazine methosulfate
vanillin + reduced phenazine methosulfate
-
-
-
?
2-Methoxy-4-n-propylphenol + O2
1-(4'-Hydroxy-3'-methoxyphenyl)propanol
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-
94% R-enantiomer of 1-(4'-hydroxy-3'-methoxyphenyl)propanol
?
2-Methoxy-4-n-propylphenol + O2
1-(4'-Hydroxy-3'-methoxyphenyl)propanol
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-
90% 4-hydroxyphenylalcohol + 10% 4-hydroxyphenylalkene. Less than 1% cis-4-hydroxyphenylalkene + more than 99% trans-4-hydroxyphenylalkene
?
4-(3'-methylcrotyl)phenol + O2
4-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]phenol + 4-[(1E)-3-methylbuta-1,3-dien-1-yl]phenol
-
-
-
-
?
4-(3'-methylcrotyl)phenol + O2
4-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]phenol + 4-[(1E)-3-methylbuta-1,3-dien-1-yl]phenol
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-
40% 4-hydroxyphenylalcohol + 60% 4-hydroxyphenylalkene. 100% trans-4-hydroxyphenylalkene
?
4-(methoxymethyl)phenol + O2 + H2O
4-hydroxybenzaldehyde + methanol + H2O2
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-
-
-
?
4-(methoxymethyl)phenol + O2 + H2O
4-hydroxybenzaldehyde + methanol + H2O2
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like native enzyme the mutant enzymes T457E, D170A and d170S preferentially form the (R)-enantiomer. The mutant enzymes D170A/T457E and D170S/T457E exhibit an inverted stereospecificity
-
?
4-(methoxymethyl)phenol + O2 + H2O
4-hydroxybenzaldehyde + methanol + H2O2
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upon reduction, a binary complex is produced composed of the p-quinone methide of 4-(methoxymethyl)phenol and reduced enzyme
-
?
4-ethylphenol + O2
1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + 4-hydroxyacetophenone
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-
76% 4-hydroxyphenolalcohol + 24% 4-hydroxyphenylalkene
?
4-ethylphenol + O2
1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + 4-hydroxyacetophenone
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-
94% R-enantiomer of 1-(4'-hydroxyphenyl)ethanol. 78% 1-(4'-hydroxyphenyl)ethanol + 18% 4-vinylphenol + 4% 4-hydroxyacetophenone
?
4-ethylphenol + O2
1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + 4-hydroxyacetophenone
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transient intermediate: p-quinone methide of the aromatic substrate in complex with reduced enzyme. Ordered sequential binding mechanism in which the rate of flavin reduction determines the turnover rate while the reduced enzyme-p-quinone methide binary complex rapidly reacts with dioxygen
-
-
?
4-ethylphenol + O2 + H2O
(R)-1-(4'-hydroxyphenyl)ethanol + H2O2
-
-
product formed by wild-type enzyme and mutant enzymes D170S and D170A.D170A/T457E and D170S/T457E form (S)-1-(4'-hydroxyphenyl)ethanol. The hydroxylation reaction in D170S is nearly completely blocked and this mutant converts short-chain alkylphenols to the corresponding alkenes. Mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 92% alcohol + 8% alkene
-
?
4-ethylphenol + O2 + H2O
(R)-1-(4'-hydroxyphenyl)ethanol + H2O2
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predominant product of wild-type enzyme and of mutant T457E
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ir
4-n-pentylphenol + O2
4-[(1E)-pent-1-en-1-yl]phenol + 4-[(1Z)-pent-1-en-1-yl]phenol + H2O2
-
-
-
-
?
4-n-pentylphenol + O2
4-[(1E)-pent-1-en-1-yl]phenol + 4-[(1Z)-pent-1-en-1-yl]phenol + H2O2
-
-
60% cis-4-hydroxyphenylalkene + 40% trans-4-hydroxyphenylalkene
?
4-Propylphenol + O2
1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
-
-
-
-
?
4-Propylphenol + O2
1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
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-
-
-
r
4-Propylphenol + O2
1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
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-
94% R-enantiomer of 1-(4'-hydroxyphenyl)propanol. 78% 1-(4'-hydroxyphenyl)propanol + 18% 4-propenylphenol + 4% 1-(4'-hydroxyphenyl)propanone
?
4-Propylphenol + O2
1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
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4-n-propylphenol
45% cis-4-hydroxyphenylalkene + 55% trans-4-hydroxyphenylalkene
?
eugenol + O2 + H2O
coniferyl alcohol + H2O2
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-
-
-
?
vanillyl alcohol + O2
vanillin + H2O2
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-
-
?
additional information
?
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enzyme also catalyzes the oxidative deamination of 4-hydroxybenzylamines and the oxidative demethylation of 4-(methoxymethyl)phenols
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-
?
additional information
?
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short-chain 4-alkylphenols are predominantly hydroxylated to (R)-1-(4'-hydroxyphenyl) alcohols, whereas medium-chain 4-alkylphenols are dehydrogenated to the corresponding 1-(4'-hydroxyphenyl) alkenes
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-
?
additional information
?
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covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process
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-
?
additional information
?
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enzyme also oxidizes eugenol. Poor substrates: vanillylamine, 4-ethylguaiacol
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