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3,4,5-trimethoxybenzoate + O2 + NADH + H+
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
3,4-dimethoxybenzoate + O2 + NADH + H+
isovanillate + NAD+ + H2O + formaldehyde
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH + H+
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
-
-
-
?
isovanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
m-anisate + O2 + NADH + H+
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
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
-
-
?
syringate + NADH + H+ + O2
?
Q08KC3; Q08KC3
-
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
vanillic acid + NADH + H+ + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratrate + NADH + H+ + O2
isovanillate + NAD+ + H2O + formaldehyde
veratric acid + NAD(P)H + H+ + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
veratric acid + NAD(P)H + H+ + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
additional information
?
-
3,4,5-trimethoxybenzoate + O2 + NADH + H+

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
-
?
3,4-dimethoxybenzoate + O2 + NADH + H+

isovanillate + NAD+ + H2O + formaldehyde
-
-
-
?
3,4-dimethoxybenzoate + O2 + NADH + H+
isovanillate + NAD+ + H2O + formaldehyde
-
-
-
?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde

m-toluate + O2 + NADH + H+
-
-
-
?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH + H+
-
-
-
?
3-hydroxymethyl-4-hydroxy-5-methylbenzoate + 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
-
?
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
-
?
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-anisate + O2 + NADH + H+

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
-
-
-
?
vanillate + O2 + NADH + H+

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
-
-
-
-
?
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
-
-
?
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
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
-
?
veratrate + NADH + H+ + O2

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
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
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 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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
Q08KC3; Q08KC3
-
-
-
?
isovanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
m-anisate + O2 + NADH + H+
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
syringate + NADH + H+ + O2
?
Q08KC3; Q08KC3
-
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
vanillic acid + NAD(P)H + H+ + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
vanillic acid + NADH + H+ + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratrate + NADH + H+ + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
veratric acid + NAD(P)H + H+ + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
veratric acid + NAD(P)H + H+ + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
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
-
-
?
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
O-demethylation by IvaAB
-
-
?
vanillate + O2 + NADH + H+

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
-
-
-
-
?
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
-
-
?
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
O-demethylation by VanA
-
-
?
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
-
?
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
O-demethylation by VanA
-
-
?
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
O-demethylation by IvaAB
-
-
?
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-
-
brenda
-
-
-
brenda
-
the cells grow in vanillate, 4-hydroxybenzoate, syringate, ferulate, p-coumarate, and 3-O-methylgallate, but not on vanillin and syringaldehyde. Maximum specific growth rates, uptake rates and yields on lignin model compounds by Microbacterium sp. RG1, overview. When strain is cultivated with 5 mM each of the aldehydes vanillin or syringaldehyde no growth is observed for more than 200 h
brenda
-
-
brenda
additional information

in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
brenda
additional information
-
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
-
brenda
additional information
-
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
-
brenda
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