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Literature summary extracted from

  • Nishimura, M.; Nishimura, Y.; Abe, C.; Kohhata, M.
    Expression and substrate range of Streptomyces vanillate demethylase (2014), Biol. Pharm. Bull., 37, 1564-1568 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.13.82 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 Streptomyces sp. NL15-2K

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.82 4-hydroxy-3-methylbenzoate + O2 + NADH + H+ Streptomyces sp. NL15-2K
-
 ?
-
 ?
1.14.13.82 m-anisate + O2 + NADH + H+ Streptomyces sp. NL15-2K
-
 m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
 ?
1.14.13.82 syringate + NADH + H+ + O2 Streptomyces sp. NL15-2K
-
 ?
-
 ?
1.14.13.82 vanillate + O2 + NADH + H+ Streptomyces sp. NL15-2K i.e. protocatechiuc acid 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
 ?
1.14.13.82 veratrate + NADH + H+ + O2 Streptomyces sp. NL15-2K
-
 isovanillate + NAD+ + H2O + formaldehyde
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.82 Streptomyces sp. NL15-2K Q08KC3 AND Q08KC3 vanillate O-demethylase oxygenase subunits A and B
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.82 4-hydroxy-3-methylbenzoate + O2 + NADH + H+
-
 Streptomyces sp. NL15-2K ?
-
 ?
1.14.13.82 4-hydroxy-3-methylbenzoate + O2 + NADH + H+
-
 Streptomyces sp. NL15-2K 4-hydroxy-3-(hydroxymethyl)benzoate + NAD+ + H2O + formaldehyde
-
 ?
1.14.13.82 m-anisate + O2 + NADH + H+
-
 Streptomyces sp. NL15-2K m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
 ?
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 ?
-
 ?
1.14.13.82 syringate + NADH + H+ + O2
-
 Streptomyces sp. NL15-2K ?
-
 ?
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
-
 ?
1.14.13.82 vanillate + O2 + NADH + H+ i.e. protocatechiuc acid Streptomyces sp. NL15-2K 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
 ?
1.14.13.82 veratrate + NADH + H+ + O2
-
 Streptomyces sp. NL15-2K isovanillate + NAD+ + H2O + formaldehyde
-
 ?
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
-
 ?

Subunits

EC Number Subunits Comment Organism
1.14.13.82 dimer 1 x 40000, subunit A + 1 * 33000, subunit B, recombinant enzyme, SDS-PAGE Streptomyces sp. NL15-2K

Synonyms

EC Number Synonyms Comment Organism
1.14.13.82 VanA
-
 Streptomyces sp. NL15-2K
1.14.13.82 vanAB
-
 Streptomyces sp. NL15-2K
1.14.13.82 VanB
-
 Streptomyces sp. NL15-2K
1.14.13.82 vanillate demethylase
-
 Streptomyces sp. NL15-2K

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.82 NADH
-
 Streptomyces sp. NL15-2K