1.14.13.82 3,4,5-trimethoxybenzoate + O2 + NADH + H+ 70% of the activity compared to vanillate Acinetobacter sp. 3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde - ? 355944 1.14.13.82 3,4,5-trimethoxybenzoate + O2 + NADH + H+ 70% of the activity compared to vanillate Acinetobacter sp. ADP1 3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde - ? 355944 1.14.13.82 3,4-dimethoxybenzoate + O2 + NADH + H+ - Acinetobacter sp. isovanillate + NAD+ + H2O + formaldehyde - ? 355941 1.14.13.82 3,4-dimethoxybenzoate + O2 + NADH + H+ - Acinetobacter sp. ADP1 isovanillate + NAD+ + H2O + formaldehyde - ? 355941 1.14.13.82 3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde - Acinetobacter sp. m-toluate + O2 + NADH + H+ - ? 355942 1.14.13.82 3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde - Acinetobacter sp. ADP1 m-toluate + O2 + NADH + H+ - ? 355942 1.14.13.82 3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H+ + ? 85% of the activity compared to vanillate Acinetobacter sp. 4-hydroxy-3,5-dimethylbenzoate + NAD+ + ? - ? 355943 1.14.13.82 3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H+ + ? 85% of the activity compared to vanillate Acinetobacter sp. ADP1 4-hydroxy-3,5-dimethylbenzoate + NAD+ + ? - ? 355943 1.14.13.82 4-hydroxy-3-methylbenzoate + O2 + NADH + H+ - Streptomyces sp. NL15-2K ? - ? 442207 1.14.13.82 4-hydroxy-3-methylbenzoate + O2 + NADH + H+ - Streptomyces sp. NL15-2K 4-hydroxy-3-(hydroxymethyl)benzoate + NAD+ + H2O + formaldehyde - ? 442911 1.14.13.82 isovanillic acid + NAD(P)H + H+ + O2 O-demethylation by IvaAB Comamonas testosteroni protocatechuic acid + NAD(P)+ + H2O + formaldehyde - ? 386511 1.14.13.82 isovanillic acid + NAD(P)H + H+ + O2 i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB Comamonas testosteroni protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386511 1.14.13.82 isovanillic acid + NAD(P)H + H+ + O2 O-demethylation by IvaAB Comamonas testosteroni BR6020 protocatechuic acid + NAD(P)+ + H2O + formaldehyde - ? 386511 1.14.13.82 isovanillic acid + NAD(P)H + H+ + O2 i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB Comamonas testosteroni BR6020 protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386511 1.14.13.82 m-anisate + O2 + NADH + H+ - Acinetobacter sp. m-hydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355940 1.14.13.82 m-anisate + O2 + NADH + H+ - Streptomyces sp. NL15-2K m-hydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355940 1.14.13.82 m-anisate + O2 + NADH + H+ - Acinetobacter sp. ADP1 m-hydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355940 1.14.13.82 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 Streptomyces sp. ? - ? 89 1.14.13.82 additional information 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 Streptomyces sp. NL15-2K ? - ? 89 1.14.13.82 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 Aspergillus sp. ? - - 89 1.14.13.82 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 Galerina autumnalis ? - - 89 1.14.13.82 syringate + NADH + H+ + O2 - Streptomyces sp. NL15-2K ? - ? 442567 1.14.13.82 syringate + NADH + H+ + O2 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 Streptomyces sp. NL15-2K 3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde - ? 443924 1.14.13.82 vanillate + O2 + NAD(P)H + H+ - Acinetobacter baylyi 3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde - ? 427569 1.14.13.82 vanillate + O2 + NADH + H+ - Pseudomonas sp. 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Corynebacterium glutamicum 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Acinetobacter sp. 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Aspergillus sp. 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Rhodococcus jostii 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Microbacterium sp. RG1 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Pseudomonas sp. NGC7 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ - Galerina autumnalis 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ able to demethylate one methoxy group or to monohydroxylate one methyl group in the meta position Acinetobacter sp. 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - r 355945 1.14.13.82 vanillate + O2 + NADH + H+ i.e. protocatechiuc acid Corynebacterium efficiens 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ i.e. protocatechiuc acid Streptomyces sp. NL15-2K 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillate + O2 + NADH + H+ i.e. protocatechiuc acid Corynebacterium efficiens NBRC 100395 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde - ? 355945 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 - Pseudomonas putida protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386759 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 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 Pseudomonas putida protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386759 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 O-demethylation by VanA Comamonas testosteroni protocatechuic acid + NAD(P)+ + H2O + formaldehyde - ? 386759 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA Comamonas testosteroni protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386759 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 O-demethylation by VanA Comamonas testosteroni BR6020 protocatechuic acid + NAD(P)+ + H2O + formaldehyde - ? 386759 1.14.13.82 vanillic acid + NAD(P)H + H+ + O2 i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA Comamonas testosteroni BR6020 protocatechuic acid + NAD(P)+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386759 1.14.13.82 vanillic acid + NADH + H+ + O2 - Streptomyces sp. protocatechuic acid + NAD+ + H2O + formaldehyde procatechuic acid is 3,4-dihydroxybenzoate ? 386760 1.14.13.82 veratrate + NADH + H+ + O2 - Streptomyces sp. NL15-2K isovanillate + NAD+ + H2O + formaldehyde - ? 442592 1.14.13.82 veratrate + NADH + H+ + O2 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 Streptomyces sp. NL15-2K isovanillate + NAD+ + H2O + formaldehyde - ? 442592 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 O-demethylation by VanA Comamonas testosteroni isovanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386761 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA Comamonas testosteroni isovanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386761 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 O-demethylation by VanA Comamonas testosteroni BR6020 isovanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386761 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA Comamonas testosteroni BR6020 isovanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386761 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 O-demethylation by IvaAB Comamonas testosteroni vanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386762 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB Comamonas testosteroni vanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386762 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 O-demethylation by IvaAB Comamonas testosteroni BR6020 vanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386762 1.14.13.82 veratric acid + NAD(P)H + H+ + O2 i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB Comamonas testosteroni BR6020 vanillic acid + NAD(P)+ + H2O + formaldehyde - ? 386762