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

3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
-
70% of the activity compared to vanillate
-
?
3,4,5-trimethoxybenzoate + O2 + NADH
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
-
70% of the activity compared to vanillate
-
?
3,4-dimethoxybenzoate + O2 + NADH

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

m-toluate + O2 + NADH
-
-
-
?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH
-
-
-
?
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 + O2

protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)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 + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)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

m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
vanillate + O2 + NADH

3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
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
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
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
Q08KC3; Q08KC3
i.e. protocatechiuc acid
-
-
?
vanillic acid + NAD(P)H + O2

protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)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 + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)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 + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)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 + O2

isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
veratrate + NADH + 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 + O2

isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2

vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
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
-
-
?
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4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
Q08KC3; Q08KC3
-
-
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
syringate + NADH + O2
?
Q08KC3; Q08KC3
-
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratrate + NADH + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3
-
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
veratric acid + NAD(P)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 + O2

protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
vanillate + O2 + NADH

3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
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
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
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
Q08KC3; Q08KC3
i.e. protocatechiuc acid
-
-
?
vanillic acid + NAD(P)H + O2

protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)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 + O2

isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2

vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
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-
-
brenda
-
-
-
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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expressed in Escherichia coli
-
expressed in Escherichia coli BL21(DE3) cells
-
expression in Escherichia coli
-
gene ivaA, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli
gene ivaB, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli
gene vanA, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli
gene vanAB, recombinant overexpression in Corynebacterium glutamicum strain F, and the strain produces vanillate from ferulic acid and the enzyme converts it to protocatechiuc acid, a precursor of polymers and plastics and a constituent of food, fed-batch biotransformation
Q8FRX4; Q8FRX3
genes vanA and vanB, DNA and amino acid sequence determination and analysis, functional coexpression of genes vanA and vanB in Escherichia coli K12 strain WV1181
-
genes vanA and vanB, DNA and amino acid sequence determination and analysis, genetic organization, sequence comparison, functional coexpression of genes vanA and vanB in Streptomyces lividans strain 1326 from the high-copy plasmid pIJ702, selection on veratric acid
-
genes vanAB, functional expression in Escherichia coli strain BL21(DE3), subcloning in Escherichia coli strain DH5alpha, VanA is expressed as a soluble protein, whereas VanB is expressed in inclusion bodies
Q08KC3; Q08KC3
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Priefert, H.; Rabenhorst, J.; Steinbuchel, A.
Molecular characterization of genes of Pseudomonas sp. strain HR199 involved in bioconversion of vanillin to protocatechuate
J. Bacteriol.
179
2595-2607
1997
Pseudomonas sp.
brenda
Morawski, B.; Segura, A.; Ornston, L.N.
Substrate range and genetic analysis of Acinetobacter vanillate demethylase
J. Bacteriol.
182
1383-1389
2000
Acinetobacter sp., Acinetobacter sp. ADP1
brenda
Morawski, B.; Segura, A.; Ornston, L.N.
Repression of Acinetobacter vanillate demethylase synthesis by VanR, a member of the GntR family of transcriptional regulators
FEMS Microbiol. Lett.
187
65-68
2000
Acinetobacter sp.
brenda
Brunel, F.; Davison, J.
Cloning and sequencing of Pseudomonas genes encoding vanillate demethylase
J. Bacteriol.
170
4924-4930
1988
Pseudomonas sp.
brenda
Merkens, H.; Beckers, G.; Wirtz, A.; Burkovski, A.
Vanillate Metabolism in Corynebacterium glutamicum
Curr. Microbiol.
51
59-65
2005
Corynebacterium glutamicum
brenda
Nishimura, M.; Ishiyama, D.; Davies, J.
Molecular cloning of Streptomyces genes encoding vanillate demethylase
Biosci. Biotechnol. Biochem.
70
2316-2319
2006
Streptomyces sp.
brenda
Hibi, M.; Sonoki, T.; Mori, H.
Functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway
FEMS Microbiol. Lett.
253
237-242
2005
Pseudomonas putida
brenda
Providenti, M.A.; OBrien, J.M.; Ruff, J.; Cook, A.M.; Lambert, I.B.
Metabolism of isovanillate, vanillate, and veratrate by Comamonas testosteroni strain BR6020
J. Bacteriol.
188
3862-3869
2006
Comamonas testosteroni (Q2KQ78), Comamonas testosteroni (Q2KQ79), Comamonas testosteroni (Q2KQ82), Comamonas testosteroni BR6020 (Q2KQ78), Comamonas testosteroni BR6020 (Q2KQ79), Comamonas testosteroni BR6020 (Q2KQ82)
brenda
Chen, H.P.; Chow, M.; Liu, C.C.; Lau, A.; Liu, J.; Eltis, L.D.
Vanillin catabolism in Rhodococcus jostii RHA1
Appl. Environ. Microbiol.
78
586-588
2012
Rhodococcus jostii
brenda
Gosling, A.; Fowler, S.J.; OShea, M.S.; Straffon, M.; Dumsday, G.; Zachariou, M.
Metabolic production of a novel polymer feedstock, 3-carboxy muconate, from vanillin
Appl. Microbiol. Biotechnol.
90
107-116
2011
Acinetobacter baylyi
brenda
Okai, N.; Masuda, T.; Takeshima, Y.; Tanaka, K.; Yoshida, K.I.; Miyamoto, M.; Ogino, C.; Kondo, A.
Biotransformation of ferulic acid to protocatechuic acid by Corynebacterium glutamicum ATCC 21420 engineered to express vanillate O-demethylase
AMB Express
7
130
2017
Corynebacterium efficiens (Q8FRX4 AND Q8FRX3), Corynebacterium efficiens NBRC 100395 (Q8FRX4 AND Q8FRX3)
brenda
Nishimura, M.; Nishimura, Y.; Abe, C.; Kohhata, M.
Expression and substrate range of Streptomyces vanillate demethylase
Biol. Pharm. Bull.
37
1564-1568
2014
Streptomyces sp. NL15-2K (Q08KC3 AND Q08KC3)
brenda