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1,2-dihydroxybenzene + CO2
2,3-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
2,3-Dihydroxybenzoate
Catechol + CO2
2,4,6-trihydroxybenzoate
benzene-1,3,5-triol + CO2
-
-
-
?
2,6-dihydroxy-4-methylbenzoate
resveratrol + CO2
-
-
-
?
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
5-methylresorcinol + CO2
2,6-dihydroxy-4-methylbenzoate
catechol + CO2
2,3-dihydroxybenzoate
gnetol + CO2
2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid
Phenol + CO2
4-Hydroxybenzoate
resorcinol + CO2
2,6-dihydroxybenzoate
-
-
-
?
resveratrol + CO2
2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoate
-
-
-
?
additional information
?
-
1,2-dihydroxybenzene + CO2
2,3-dihydroxybenzoate
-
-
enzyme catalyzes the regioselective carboxylation
-
r
1,2-dihydroxybenzene + CO2
2,3-dihydroxybenzoate
-
-
enzyme catalyzes the regioselective carboxylation
-
r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
-
?, r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
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%
-
r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
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%
-
r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
-
?, r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
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%)
-
r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
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%)
-
r
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
-
-
-
r
2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
-
146% of the activity with 2,6-dihydroxybenzoate
-
-
r
2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
-
146% of the activity with 2,6-dihydroxybenzoate
-
-
r
2,3-Dihydroxybenzoate
Catechol + CO2
-
-
-
r
2,3-Dihydroxybenzoate
Catechol + CO2
-
-
-
r
2,3-Dihydroxybenzoate
Catechol + CO2
-
-
-
?
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
-
r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
?, r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
-
r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
?, r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
-
r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
-
r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
?
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
r
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
-
-
-
-
?
5-methylresorcinol + CO2
2,6-dihydroxy-4-methylbenzoate
-
-
-
?
5-methylresorcinol + CO2
2,6-dihydroxy-4-methylbenzoate
-
-
-
?
catechol + CO2
2,3-dihydroxybenzoate
-
-
-
?
catechol + CO2
2,3-dihydroxybenzoate
-
-
-
r
catechol + CO2
2,3-dihydroxybenzoate
-
-
-
?
gnetol + CO2
2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid
-
-
-
?
gnetol + CO2
2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid
-
-
-
?
Phenol + CO2
4-Hydroxybenzoate
-
-
enzyme catalyzes the regioselective carboxylation
-
r
Phenol + CO2
4-Hydroxybenzoate
-
-
enzyme catalyzes the regioselective carboxylation
-
r
piceatannol + CO2
?
-
-
-
?
piceatannol + CO2
?
-
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
no substrates: 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 3,4-dihydroxybenzoate, 3,5-dihydroxybenzoate, 2-hydroxybenzoate, or 3-hydroxybenzoate
-
-
?
additional information
?
-
-
no substrates: 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 3,4-dihydroxybenzoate, 3,5-dihydroxybenzoate, 2-hydroxybenzoate, or 3-hydroxybenzoate
-
-
?
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Cu2+
-
1 mM, 26% loss of activity
diethyl dicarbonate
1 mM, 66% of initial activity for decarboxylation reaction, 62% of initial activity for carboxylation reaction
p-chloromercuribenzoate
-
1 mM, 20% loss of activity
Ag+
-
1 mM, 100% loss of activity
Ag+
1 mM, 0% of initial activity for decarboxylation reaction, 12% of initial activity for carboxylation reaction
Hg2+
-
1 mM, 47% loss of activity
Hg2+
1 mM, 21% of initial activity for decarboxylation reaction, 94% of initial activity for carboxylation reaction
additional information
-
not inhibitory: FeCl3, FeSO4, CoCl2, MgSO4, MnCl2, NiCl2, CaCl2, ZnSO4, EDTA, Tiron, 2,2?-bipyridyl, o-phenanthroline, 8-hydroxyquinoline, phenylhydrazine, hydroxylamine, iodoacetate, N-ethylmaleimide or NaBH4
-
additional information
not inhibitory: presence of oxygen
-
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Yoshida, M.; Oikawa, T.; Obata, H.; Abe, K.; Mihara, H.; Esaki, N.
Biochemical and genetic analysis of the gamma-resorcylate (2,6-dihydroxybenzoate), aatabolic pathway in Rhizobium sp. strain MTP-10005: Identification and functional analysis of its gene cluster
J. Bacteriol.
189
1573-1581
2006
Rhizobium sp. (Q60GU1), Rhizobium sp.
brenda
Kasai, D.; Araki, N.; Motoi, K.; Yoshikawa, S.; Iino, T.; Imai, S.; Masai, E.; Fukuda, M.
gamma-Resorcylate catabolic-pathway genes in the soil actinomycete Rhodococcus jostii RHA1
Appl. Environ. Microbiol.
81
7656-7665
2015
Rhodococcus jostii
brenda
Matsui, T.; Yoshida, T.; Yoshimura, T.; Nagasawa, T.
Regioselective carboxylation of 1,3-dihydroxybenzene by 2,6-dihydroxybenzoate decarboxylase of Pandoraea sp. 12B-2
Appl. Microbiol. Biotechnol.
73
95-102
2006
Pandoraea sp., Pandoraea sp. 12B-2
brenda
Yoshida, T.; Hayakawa, Y.; Matsui, T.; Nagasawa, T.
Purification and characterization of 2,6-dihydroxybenzoate decarboxylase reversibly catalyzing nonoxidative decarboxylation
Arch. Microbiol.
181
391-397
2004
Agrobacterium tumefaciens, Agrobacterium tumefaciens IAM12048
brenda
Ishii, Y.; Narimatsu, Y.; Iwasaki, Y.; Arai, N.; Kino, K.; Kirimura, K.
Reversible and nonoxidative gamma-resorcylic acid decarboxylase: Characterization and gene cloning of a novel enzyme catalyzing carboxylation of resorcinol, 1,3-dihydroxybenzene, from Rhizobium radiobacter
Biochem. Biophys. Res. Commun.
324
611-620
2004
Agrobacterium tumefaciens (Q60FX6), Agrobacterium tumefaciens WU-0108 (Q60FX6)
brenda
Yoshida, M.; Fukuhara, N.; Oikawa, T.
Thermophilic, reversible gamma-resorcylate decarboxylase from Rhizobium sp. strain MTP-10005: purification, molecular characterization, and expression
J. Bacteriol.
186
6855-6863
2004
Rhizobium sp. (Q60GU1), Rhizobium sp.
brenda
Goto, M.; Hayashi, H.; Miyahara, I.; Hirotsu, K.; Yoshida, M.; Oikawa, T.
Crystal structures of nonoxidative zinc-dependent 2,6-dihydroxybenzoate (gamma-resorcylate) decarboxylase from Rhizobium sp. strain MTP-10005
J. Biol. Chem.
281
34365-34373
2006
Rhizobium sp. (Q60GU1)
brenda
Sheng, X.; Patskovsky, Y.; Vladimirova, A.; Bonanno, J.B.; Almo, S.C.; Himo, F.; Raushel, F.M.
Mechanism and structure of gamma-resorcylate decarboxylase
Biochemistry
57
3167-3175
2018
Polaromonas sp. JS666 (Q12BV1)
brenda
Sato, M.; Sakurai, N.; Suzuki, H.; Shibata, D.; Kino, K.
Enzymatic carboxylation of hydroxystilbenes by the gamma-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions
J. Mol. Catal. B
122
348-352
2015
Agrobacterium tumefaciens (Q60FX6), Agrobacterium tumefaciens WU-0108 (Q60FX6)
-
brenda