4.1.1.103: gamma-resorcylate decarboxylase
This is an abbreviated version!
For detailed information about gamma-resorcylate decarboxylase, go to the full flat file.
Reaction
Synonyms
graF, Rdc, TsdA
ECTree
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Substrates Products
Substrates Products on EC 4.1.1.103 - gamma-resorcylate decarboxylase
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REACTION DIAGRAM
resveratrol + CO2
2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoate
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-
-
?
2,3-dihydroxybenzoate
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-
enzyme catalyzes the regioselective carboxylation
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r
1,2-dihydroxybenzene + CO2
2,3-dihydroxybenzoate
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enzyme catalyzes the regioselective carboxylation
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r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
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in the presence of KHCO3, the enzyme catalyzes the regioselective carboxylation of 1,3-dihydroxybenzene into 2,6-dihydroxybenzoate at a molar conversion ratio of 30%
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r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
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in the presence of KHCO3, the enzyme catalyzes the regioselective carboxylation of 1,3-dihydroxybenzene into 2,6-dihydroxybenzoate at a molar conversion ratio of 30%
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r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
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-
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?, r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
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-
reaction is reversible. In the presence of 0.1 M KHCO3, 0.5 mM 2,6-dihydroxybenzoate is formed from 12.5 mM 1,3-dihydroxybenzene. With 3 M KHCO3, the molar conversion ratio of 1,3-dihydroxybenzene reaches its highest value (48%)
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r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
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-
reaction is reversible. In the presence of 0.1 M KHCO3, 0.5 mM 2,6-dihydroxybenzoate is formed from 12.5 mM 1,3-dihydroxybenzene. With 3 M KHCO3, the molar conversion ratio of 1,3-dihydroxybenzene reaches its highest value (48%)
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r
1,2-dihydroxybenzene + CO2
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146% of the activity with 2,6-dihydroxybenzoate
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r
2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
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146% of the activity with 2,6-dihydroxybenzoate
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r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
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-
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r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
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?, r
2,6-dihydroxy-4-methylbenzoate
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-
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?
5-methylresorcinol + CO2
2,6-dihydroxy-4-methylbenzoate
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-
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?
2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid
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-
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?
gnetol + CO2
2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid
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-
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?
4-Hydroxybenzoate
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enzyme catalyzes the regioselective carboxylation
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r
Phenol + CO2
4-Hydroxybenzoate
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enzyme catalyzes the regioselective carboxylation
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r
?
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no substrates: 2,4-dihydroxybenzoate, 4-hydroxybenzoate, 3-hydroxybenzoate, 2-hydroxybenzoate, 4-methoxybenzoate, 4-aminobenzoate, 2,4,6-trihydroxybenzoate and 3,4,5-trihydroxybenzoate, benzoate and terephthalate
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?
additional information
?
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the enzyme introduces a carboxyl group preferentially at the 2 position of the 1,3-dihydroxybenzene moiety, with the exception of catechol, where position 3 is carboxylated. With the exception of catechol, compounds having the 1,2-dihydroxybenzene moiety in the structures such as 4-methylcatechol, butein, quercetin, fisetin, 3',4',5,7-tetrahydroxyflavone, 7,8-dihydroxyflavone and catechin give no reaction products
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?
additional information
?
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no substrates: 2,4-dihydroxybenzoate, 4-hydroxybenzoate, 3-hydroxybenzoate, 2-hydroxybenzoate, 4-methoxybenzoate, 4-aminobenzoate, 2,4,6-trihydroxybenzoate and 3,4,5-trihydroxybenzoate, benzoate and terephthalate
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?
additional information
?
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the enzyme introduces a carboxyl group preferentially at the 2 position of the 1,3-dihydroxybenzene moiety, with the exception of catechol, where position 3 is carboxylated. With the exception of catechol, compounds having the 1,2-dihydroxybenzene moiety in the structures such as 4-methylcatechol, butein, quercetin, fisetin, 3',4',5,7-tetrahydroxyflavone, 7,8-dihydroxyflavone and catechin give no reaction products
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?
additional information
?
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in the proposed reaction mechanism, gamma-resorcylate binds 2,6-dihydroxybenzoate by direct coordination of the active site manganese ion to the carboxylate anion of the substrate and one of the adjacent phenolic oxygens. The enzyme subsequently catalyzes the transfer of a proton to C1 of gamma-resorcylate prior to the actual decarboxylation step
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?
additional information
?
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no substrates: 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 3,4-dihydroxybenzoate, 3,5-dihydroxybenzoate, 2-hydroxybenzoate, or 3-hydroxybenzoate
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-
?
additional information
?
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no substrates: 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 3,4-dihydroxybenzoate, 3,5-dihydroxybenzoate, 2-hydroxybenzoate, or 3-hydroxybenzoate
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?