1.14.13.82: vanillate monooxygenase
This is an abbreviated version!
For detailed information about vanillate monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.82
-
1.14.13.82
-
protocatechuate
-
lignin
-
ferulic
-
syringate
-
veratrate
-
o-demethylation
-
lignin-derived
-
3,4-dioxygenase
-
3,4-dihydroxybenzoate
-
dehalogenans
-
corrinoid
-
acetobacterium
- 1.14.13.82
- protocatechuate
- lignin
-
ferulic
- syringate
- veratrate
-
o-demethylation
-
lignin-derived
-
3,4-dioxygenase
- 3,4-dihydroxybenzoate
- dehalogenans
- corrinoid
-
acetobacterium
Reaction
Synonyms
4-hydroxy-3-methoxybenzoate demethylase, EC 1.2.3.12, IvaAB, More, VAN, VanA, vanAB, VanB, vanillate demethylase, vanillate O-demethylase, vanillate O-demethylase oxygenase, vanillate-O-demethylase, vanillic acid O-demethylase
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 1.14.13.82 - vanillate monooxygenase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
REACTION DIAGRAM
3,4,5-trimethoxybenzoate + O2 + NADH + H+
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H+ + ?
4-hydroxy-3,5-dimethylbenzoate + NAD+ + ?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
4-hydroxy-3-(hydroxymethyl)benzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
Q08KC3; Q08KC3
-
-
-
?
syringate + NADH + H+ + O2
3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
3,4-dihydroxy-5-methoxybenzoate, and gallate are produced from syringate, one of the two methoxy groups in the meta-position of syringate is demethylated first, and then the second methoxy group is demethylated at a slower rate
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillic acid + NADH + H+ + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
-
70% of the activity compared to vanillate
-
?
3,4,5-trimethoxybenzoate + O2 + NADH + H+
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
-
70% of the activity compared to vanillate
-
?
isovanillate + NAD+ + H2O + formaldehyde
-
-
-
?
3,4-dimethoxybenzoate + O2 + NADH + H+
isovanillate + NAD+ + H2O + formaldehyde
-
-
-
?
m-toluate + O2 + NADH + H+
-
-
-
?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH + H+
-
-
-
?
4-hydroxy-3,5-dimethylbenzoate + NAD+ + ?
-
85% of the activity compared to vanillate
-
?
3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H+ + ?
4-hydroxy-3,5-dimethylbenzoate + NAD+ + ?
-
85% of the activity compared to vanillate
-
?
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB
procatechuic acid is 3,4-dihydroxybenzoate
-
?
isovanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB
procatechuic acid is 3,4-dihydroxybenzoate
-
?
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
m-anisate + O2 + NADH + H+
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
m-anisate + O2 + NADH + H+
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
able to demethylate one methoxy group or to monohydroxylate one methyl group in the meta position
-
r
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4; Q8FRX3
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4; Q8FRX3
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Pseudomonas sp. NGC7
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
i.e. protocatechiuc acid
-
-
?
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway, formaldehyde is further converted to formate by glutathione-dependent formaldehyde dehydrogenase, encoded by gene frmA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
veratrate + NADH + H+ + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
demethylation product of veratrate is isovanillate rather than vanillate, 1H-NMR analysis. O-Demethylation of veratrate by Streptomyces vanillate demethylase occurs only at the meta-position relative to the carboxyl group
-
-
?
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + H+ + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + H+ + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + H+ + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + H+ + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + H+ + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + H+ + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
?
-
-
to detect fungal demethylation and release of catechol-like structures, these are demonstrated using catechol, gallic acid and caffeic acid as standard model compounds to forms mono, bis- and/or tris-catechol-Fe3+ complexes. The catechol-Fe3+ complexes formation controlled by pH via the deprotonation of the catechol hydroxyls is investigated at pH 2.5, 8.0 and 10.0 and demonstrates that catechol formed mono, bis- and/or tris-catechol-Fe3+ complexes, and show maximum absorbance at 547 nm. Lignin demethylation (O-demethylase) and formation of dicatecholic structures is detected. The produced aromatic vicinal diol groups in lignin model compounds (LMCs) and KL are determined using different catecholic-binding reagents with the influence of H2O2, along with 4-antiaminopyrine reagent, and are analyzed by the following: 1. Fe3+-catechol complexation method, 2. HNO2 method, 3. FAS (ferric ammonium-sulfate) method, and 4. Ti(III)-NTA (titanium (III)-nitrilotriacetate) method for hydrolytic zone formation. Among the tested methods, Fe3+-catechol complexation shows lytic zone formation, mechanism, overview
-
-
-
additional information
?
-
-
to detect fungal demethylation and release of catechol-like structures, these are demonstrated using catechol, gallic acid and caffeic acid as standard model compounds to forms mono, bis- and/or tris-catechol-Fe3+ complexes. The catechol-Fe3+ complexes formation controlled by pH via the deprotonation of the catechol hydroxyls is investigated at pH 2.5, 8.0 and 10.0 and demonstrates that catechol formed mono, bis- and/or tris-catechol-Fe3+ complexes, and show maximum absorbance at 547 nm. Lignin demethylation (O-demethylase) and formation of pyrocatecholic structures is detected. The produced aromatic vicinal diol groups in lignin model compounds (LMCs) and KL are determined using different catecholic-binding reagents with the influence of H2O2, along with 4-antiaminopyrine reagent, and are analyzed by the following: 1. Fe3+-catechol complexation method, 2. HNO2 method, 3. FAS (ferric ammonium-sulfate) method, and 4. Ti(III)-NTA (titanium (III)-nitrilotriacetate) method for hydrolytic zone formation. Among the tested methods, Fe3+-catechol complexation shows lytic zone formation, mechanism, overview
-
-
-
additional information
?
-
-
the enzyme forms a vanillate demethylase complex of VanA, a terminal oxygenase subunit, with VanB, a ferredoxin-like subunit, performing demethylation of vanillic acid and veratric acid
-
-
?
additional information
?
-
Q08KC3; Q08KC3
substrate specificity for vanillate analogues by an in vivo assay using recombinant whole cells: among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate are good substrates, whereas ferulate, vanillin, and guaiacol are not recognized by Streptomyces vanillate demethylase. Besides vanillate, 4-hydroxy-3-methylbenzoate is a better substrate than m-anisate and veratrate, and the 3-methyl group is efficiently oxidized to a hydroxymethyl group. The combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. Demethylation by Streptomyces vanillate demethylase occurs only at the 3-position of veratrate and not at the 4-position
-
-
?