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EC Tree
IUBMB Comments In the reverse direction the enzyme catalyses the regioselective carboxylation of phenol into stoichiometric amounts of salicylate. The enzyme also catalyses the reversible decarboxylation of 2,4-dihydroxybenzoate, 2,6-dihydroxybenzoate, 2,3-dihydroxybenzoate and 4-aminosalicylate .
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
salicylic acid decarboxylase, SCD, SDC,
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salicylic acid decarboxylase
salicylic acid decarboxylase
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salicylic acid decarboxylase
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SCD
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salicylate = phenol + CO2
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salicylate carboxy-lyase
In the reverse direction the enzyme catalyses the regioselective carboxylation of phenol into stoichiometric amounts of salicylate. The enzyme also catalyses the reversible decarboxylation of 2,4-dihydroxybenzoate, 2,6-dihydroxybenzoate, 2,3-dihydroxybenzoate and 4-aminosalicylate [1].
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2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
2,4-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
2,6-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
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i.e gamma-resorcylic acid
i.e. resorcinol
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r
4-aminosalicylate
3-aminophenol + CO2
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r
ginkgolic acid C15:1
3-(8Z-pentadecenyl)-phenol + CO2
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?
additional information
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2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
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i.e. catechol
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r
2,3-dihydroxybenzoate
1,2-dihydroxybenzene + CO2
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i.e. catechol
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r
2,4-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
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i.e beta-resorcylic acid
i.e. resorcinol
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r
2,4-dihydroxybenzoate
1,3-dihydroxybenzene + CO2
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i.e beta-resorcylic acid
i.e. resorcinol
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r
salicylate
phenol + CO2
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salicylate
phenol + CO2
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in the reverse direction the enzyme catalyses the regioselective carboxylation of phenol into stoichiometric amounts of salicylic acid
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r
salicylate
phenol + CO2
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?
salicylate
phenol + CO2
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in the reverse direction the enzyme catalyses the regioselective carboxylation of phenol into stoichiometric amounts of salicylic acid
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r
additional information
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the enzyme does not catalyse the carboxylation of cresol. The enzyme does not catalyse the decarboxylation of 3-hydroxybenzoate, 4-hydroxybenzoate, 3,4-dihydroxybenzoate, 5-dihydroxybenzoate, 3-methylsalicylate, 4-methylsalicylate, and vanillic acid (4-hydroxy-3-methoxybenzoate). The substrate recognition of the enzyme for decarboxylation seems to depend strictly on hydroxybenzoic acid with two neighboring hydroxyl and carboxyl groups in the active center of the enzyme
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additional information
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the enzyme does not catalyse the carboxylation of cresol. The enzyme does not catalyse the decarboxylation of 3-hydroxybenzoate, 4-hydroxybenzoate, 3,4-dihydroxybenzoate, 5-dihydroxybenzoate, 3-methylsalicylate, 4-methylsalicylate, and vanillic acid (4-hydroxy-3-methoxybenzoate). The substrate recognition of the enzyme for decarboxylation seems to depend strictly on hydroxybenzoic acid with two neighboring hydroxyl and carboxyl groups in the active center of the enzyme
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?
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salicylate
phenol + CO2
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salicylate
phenol + CO2
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additional information
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the enzyme does not require pyridoxal 5'-phosphate, NADH, and NADPH
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Fe2+
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1 mM, 1.5fold stimulation of carboxylation activity, no effect on decarboxylation activity
Zn2+
presence of Zn2+ in the active center
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AgNO3
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1 mM, complete loss of decarboxylation activity, 60% loss of carboxylation activity
CuCl2
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1 mM, 70% loss of carboxylation activity, 14% loss of decarboxylation activity
diethyl dicarbonate
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1 mM, 37% inhibition of carboxylation activity, 21% inhibition of decarboxylation activity
HgCl2
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1 mM, complete inhibition of decarboxylation activity, 94% loss of carboxylation activity
hydroxylamine
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1 mM, 23% inhibition of carboxylation activity, 9% inhibition of decarboxylation activity
NEM
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1 mM, 28% loss of carboxylation activity, 6% loss of decarboxylation activity
NiCl2
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1 mM, 85% loss carboxylation activity, 46% loss of decarboxylation activity
p-chloromercuribenzoic acid
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0.2 mM, 49% loss of carboxylation activity, 82% loss of decarboxylation activity
additional information
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the enzyme is oxygen-insensitive
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0.046
ginkgolic acid C15:1
pH not specified in the publication, 40°C
123
phenol
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pH 5.5, 30°C
1.08
salicylate
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pH 5.5, 40°C
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1.1
phenol
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pH 5.5, 30°C
0.034
salicylate
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pH 5.5, 40°C
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0.47
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pH 5.5, 40°C, production of phenol from salicylic acid
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5.5
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production of phenol from salicylate
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5 - 8.5
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pH 5.0: about 75% of maximal activity, pH 8.5: about 50% of maximal activity, production of phenol from salicylate
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30
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carboxylation activity
40
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assay at, decarboxylation activity
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20 - 30
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20°C: about 35% of maximal activity, 30°C: maximal activity, 40°C: about 10% of maximal activity, production of salicylate from phenol
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brenda
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brenda
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UniProt
brenda
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brenda
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SDC_CUTMO
350
0
39961
Swiss-Prot
other Location (Reliability: 2 )
S6FP95_9BACI
75
0
8392
TrEMBL
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40000
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4 * 40000, SDS-PAGE
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homotetramer
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4 * 40000, SDS-PAGE
homotetramer
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4 * 40000, SDS-PAGE
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homology modeling of structure and molecular docking of substrates salicylic acid and ginkgolic acid C15:1
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30
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1 h, carboxylation activity is stable up to
40
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1 h, decarboxylation activity is stable up to, 60% of the carboxylation activity is retained
50
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1 h, 40% of the decarboxylation activity is retained
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the enzyme is oxygen insensitive
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707400
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expression in Escherichia coli
recombinant Escherichia coli expressing sdc converts 40 mM phenol to 10.6 mM salicylate with a 27% (mol/mol) yield at 30°C for 9 h
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synthesis
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selective and ecological production by carboxylation of phenol to form salicylate, the enzymatic Kolbe–Schmitt reaction
synthesis
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selective and ecological production by carboxylation of phenol to form salicylate, the enzymatic Kolbe–Schmitt reaction
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Kirimura, K.; Gunji, H.; Wakayama, R.; Hattori, T.; Ishii, Y.
Enzymatic Kolbe-Schmitt reaction to form salicylic acid from phenol: enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase
Biochem. Biophys. Res. Commun.
394
279-284
2010
Cutaneotrichosporon moniliiforme, Cutaneotrichosporon moniliiforme WU-0401
brenda
Hu, Y.; Hua, Q.; Sun, G.; Shi, K.; Zhang, H.; Zhao, K.; Jia, S.; Dai, Y.; Wu, Q.
The catalytic activity for ginkgolic acid biodegradation, homology modeling and molecular dynamic simulation of salicylic acid decarboxylase
Comput. Biol. Chem.
75
82-90
2018
Cutaneotrichosporon moniliiforme (P0CT50)
brenda
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4.1.1.91 salicylate decarboxylase
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