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Information on EC 4.1.1.61 - 4-hydroxybenzoate decarboxylase
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EC Tree
4.1.1.61 4-hydroxybenzoate decarboxylaseSpecify your search results
Word Map
- 4.1.1.61
-
oxygen-sensitive
- phenylphosphate
-
denitrifying
-
nonoxidative
- 3,4-dihydroxybenzoate
-
p-hydroxyl
- aromaticum
- synthesis
- decarboxylases
-
aromatoleum
-
enterobacter
- catechol
- biotechnology
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms
4-hydroxybenzoate decarboxylase, phenol carboxylase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Decarboxylase, p-hydroxybenzoate
-
-
-
-
HBDC
KpdB
p-Hydroxybenzoate decarboxylase
-
-
-
-
Phenol carboxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxybenzoate = phenol + CO2
biological Kolbe-Schmitt carboxylation. The formation of an enzyme-bound phenolate anion from the activated phenolic compound is the rate-determining step in the carboxylation reaction
-
4-hydroxybenzoate = phenol + CO2
biological Kolbe-Schmitt carboxylation. The formation of an enzyme-bound phenolate anion from the activated phenolic compound is the rate-determining step in the carboxylation reaction
-
-
4-hydroxybenzoate = phenol + CO2
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
decarboxylation
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxybenzoate carboxy-lyase (phenol-forming)
-
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CAS REGISTRY NUMBER
COMMENTARY
37290-53-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-methoxy-4-hydroxybenzoate
2-methoxyphenol + CO2
vanillate
guaiacol
-
?
3,4-dihydroxybenzoate
benzene-1,2-diol + CO2
-
activity toward 3,4-dihydroxybenzoate at 5 mM is 2.8% of that toward 4-hydroxybenzoate
-
-
?
3,4-dihydroxybenzoate
benzene-1,2-diol + CO2
-
activity toward 3,4-dihydroxybenzoate at 5 mM is 2.8% of that toward 4-hydroxybenzoate
-
-
?
3,5-Dimethoxy-4-hydroxybenzoate
1,3-Dimethoxy-2-hydroxybenzene + CO2
-
-
-
-
?
3,5-Dimethoxy-4-hydroxybenzoate
1,3-Dimethoxy-2-hydroxybenzene + CO2
-
-
-
-
?
Phenol + CO2
4-Hydroxybenzoate
-
carboxylation in the presence of 3 M KHCO3 and 20 mM phenol with a molar conversion yield of 19%
-
-
?
Phenol + CO2
4-Hydroxybenzoate
-
carboxylation in the presence of 3 M KHCO3 and 20 mM phenol with a molar conversion yield of 19%
-
-
?
additional information
?
-
no reaction with: 3-hydroxybenzoate, 2,3-dihydroxybenzoate, 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 2,6-dihydroxybenzoate, and 3,4-dihydroxybenzoate, 2,3,4-trihydroxybenzoate and 3,4,5-trihydroxybenzoate, 3,5-dihydroxy-2-naphthalene dicarboxylate, 2,8-dihydroxynaphthoate, 5-hydroxyisophthalate, 1-hydroxy-2-naphthoate, 2-hydroxy-1-naphthoate, 3-hydroxy-2-naphthoate, 6-hydroxynicotinate, 2-hydroxypyridine-3-carboxylate, 3-hydroxypyridine-2-carboxylate
-
-
?
additional information
?
-
-
no reaction with: 3-hydroxybenzoate, 2,3-dihydroxybenzoate, 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 2,6-dihydroxybenzoate, and 3,4-dihydroxybenzoate, 2,3,4-trihydroxybenzoate and 3,4,5-trihydroxybenzoate, 3,5-dihydroxy-2-naphthalene dicarboxylate, 2,8-dihydroxynaphthoate, 5-hydroxyisophthalate, 1-hydroxy-2-naphthoate, 2-hydroxy-1-naphthoate, 3-hydroxy-2-naphthoate, 6-hydroxynicotinate, 2-hydroxypyridine-3-carboxylate, 3-hydroxypyridine-2-carboxylate
-
-
?
additional information
?
-
-
benzoate, 2-hydroxybenzoate, 3-hydroxybenzoate, 2,6-dihydroxybenzoate, 2,4,6-trihydroxybenzoate, 3,4,5-trihydroxybenzoate, terephthalate, vanillate, 4-methoxybenzoate, 4-aminobenzoate, and 6-hydroxy-2-naphthoate are inert as substrates
-
-
?
additional information
?
-
-
benzoate, 2-hydroxybenzoate, 3-hydroxybenzoate, 2,6-dihydroxybenzoate, 2,4,6-trihydroxybenzoate, 3,4,5-trihydroxybenzoate, terephthalate, vanillate, 4-methoxybenzoate, 4-aminobenzoate, and 6-hydroxy-2-naphthoate are inert as substrates
-
-
?
additional information
?
-
-
catalyzes a CO2:4-hydroxybenzoate isotope exchange reaction
-
-
?
additional information
?
-
-
induced after anaerobic growth on phenol
-
-
?
additional information
?
-
-
catalyzes a CO2:4-hydroxybenzoate isotope exchange reaction
-
-
?
additional information
?
-
-
no substrates are 2-hydroxybenzoate, 3-hydroxybenzoate, 2,3-dihydroxybenzoate, 2,4-dihydroxybenzoate, 2,5-dihydroxybenzoate, 2,3,4-trihydroxybenzoate, 3,4,5-trihydroxybenzoate
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
induced after anaerobic growth on phenol
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
not dependent on biotin, ATP, thiamin or pyridoxal phosphate
-
additional information
-
not dependent on biotin, ATP, thiamin or pyridoxal phosphate
-
additional information
-
the activity of 4-hydroxybenzoate decarboxylase is independent of pyridoxal 5'-phosphate, thiamine diphosphate, and the pyruvoyl group
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
-
can replace to some extent for Mn2+ in the CO2:4-hydroxybenzoate isotope exchange reaction
Fe2+
K+
Mg2+
Mn2+
Na+
NH4+
Rb+
Zn2+
additional information
Fe2+
-
can replace to some extent for Mn2+ in the CO2:4-hydroxybenzoate isotope exchange reaction
K+
-
phenol carboxylase activity and the two 4-hydroxybenzoate decarboxylase activities are strictly dependent on
K+
-
phenol carboxylase activity and the two 4-hydroxybenzoate decarboxylase activities are strictly dependent on
Mg2+
-
can replace to some extent for Mn2+ in the CO2:4-hydroxybenzoate isotope exchange reaction
Mn2+
-
restores activity of the decarboxylase with pH-optimum 6.4 and of the carboxylase after EDTA treatment, no effect in decarboxylase with pH-optimum 7.8
Mn2+
-
restores activity of the decarboxylase with pH-optimum 6.4 and of the carboxylase after EDTA treatment, no effect in decarboxylase with pH-optimum 7.8
Mn2+
-
minor stimulation of carboxylation of 4-hydroxybenzoate
Rb+
-
can replace K+ in the phenol carboxylase and partially in both decarboxylases
Rb+
-
can replace K+ in the phenol carboxylase and partially in both decarboxylases
Rb+
-
can replace to some extent for K+ in the CO2:4-hydroxybenzoate isotope exchange reaction
additional information
-
AgNO3, FeCl2, CoCl2, NiCl2, and FeSO4 do not affect activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NH4+
-
decreases carboxylation of 3,4-dihydroxybenzoate by about 20%
Rb+
-
decreases carboxylation of 3,4-dihydroxybenzoate by about 20%
Zn2+
-
destroys carboxylation activity towards 4-hydroxybenzoate and 3,4-dihydroxybenzoate
additional information
-
not significantly affected by phenylhydrazine or hydroxylamine
-
2,3,4-Trihydroxybenzoate
-
complete inhibition of carboxylation of phenol
2,4,6-Trihydroxybenzoate
-
complete inhibition of carboxylation of phenol
3,4,5-Trihydroxybenzoate
-
slight inhibition of carboxylation of phenol
EDTA
-
47% inhibition at 5 mM, Mg2+, Mn2+, Zn2+ or Ca2+ protect, Fe2+ does not
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
1 mM pyridoxal 5'-phosphate or thiamine diphosphate do not enhance activity
-
additional information
-
no stimulation by ATP up to 5 mM or phenylphosphate
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6.8
3,4-dihydroxybenzoate
-
in 100 mM potassium phosphate buffer (pH 7.0)
0.21
4-hydroxybenzoate
-
in 20 mM Tris-HCl (pH 7.5) containing 1 mM Mg2+, at 30°C
14.8
phenol
-
20 mM phenol, 3 MKHCO3, 10 mM dithiothreitol in 100 mM potassium phosphate buffer (pH 7.0)
additional information
additional information
4-hydroxybenzoate as substrate Km = 1 mmol/l
-
additional information
additional information
-
4-hydroxybenzoate as substrate Km = 1 mmol/l
-
additional information
additional information
vanillate as substrate Km = 4 mmol/l
-
additional information
additional information
-
vanillate as substrate Km = 4 mmol/l
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
11
BsdCD, genes encoding the BsdCD are heterologously expressed in Escherichia coli from the plasmid pTrcHisC, 3-methoxy-4-hydroxybenzoate as substrate
14
BsdCD, genes encoding the BsdCD are heterologously expressed in Escherichia coli from the plasmid pTrcHisC, 4-hydroxybenzoate as substrate
16
BsdBCD, genes encoding the BsdBCD are expressed in Escherichia coli from the plasmid pUC18, 3-methoxy-4-hydroxybenzoate as substrate
23
BsdBCD, genes encoding the BsdBCD are expressed in Escherichia coli from the plasmid pUC18, 4-hydroxybenzoate as substrate
25
3-methoxy-4-hydroxybenzoate-induced, 3-methoxy-4-hydroxybenzoate as substrate
30
4-hydroxybenzoate-induced, 3-methoxy-4-hydroxybenzoate as substrate
6
3-methoxy-4-hydroxybenzoate-induced, 4-hydroxybenzoate as substrate
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.4
6.5
7.8
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
37
41
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
in an anaerobic consortium with Methanospirillum hungatei, one phenol carboxylase activity and two 4-hydroxybenzoate decarboxylase activities with distinct properties
-
-
brenda
AFH12530 i.e. subunit YclB, AFH12529 i.e. subunit YclC, AFH12528 i.e. subunit YclD
AFH12530; AFH12529; AFH12528
GenBank
brenda
AFH12530 i.e. subunit YclB, AFH12529 i.e. subunit YclC, AFH12528 i.e. subunit YclD
AFH12530; AFH12529; AFH12528
GenBank
brenda
in an anaerobic consortium with Desulfovibrio sp., one phenol decarboxylase activity and two 4-hydroxybenzoate decarboxylase activities with distinct properties
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
induced in growing and resting cells by 4-hydroxybenzoate
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Show AA Sequence and Transmembrane Helices (231 entries)
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
homohexamer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20
-
when the enzyme is incubated at temperatures up to 20°C for 30 min, activity is barely decreased
30 - 60
-
treatment at 30, 40, 50, and 60°C causes 32, 43, 96, and 100% losses of the initial activity, respectively
40 - 50
-
loses more than 50% decarboxylase activity at 40°C for 5 min, and less than 25% enzyme activity remains after incubation at 50°C for 5 min
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
extremely sensitive to oxygen, in contact with air, loss of activity within a few hours
-
oxygen sensitive, loss of 50% of activity after 1 h in presence of air at 4°C compared to no activity lost after 7 days under anaerobic conditions at 4°C
-
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
oxygen-sensitive, 50% loss of activity when exposed to air at 5°C for 2 h
-
4740
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, gas atmosphere N2/H2, 95%:5%, in potassium phosphate buffer, pH 7.8, stable for months
-20C, gas atmosphere N2/H2, 95%:5%, in potassium phosphate buffer, pH 7.8, stable for months
-
-20C, gas atmosphere N2/H2, 95%:5%, in potassium phosphate buffer, pH 7.8, stable for months
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
DEAE-Sephacel column chromatography, phenyl-Sepharose CL-4B column chromatography, and butyl-Toyopearl 650M column chromatography
-
under anaerobic conditions (oxygen-free N2) at 4°C by affinity chromatography
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
-
use of enzyme for conversion of phenol into 4-hydroxybenzoic acid
synthesis
synthesis
AFH12530; AFH12529; AFH12528
construction of a phenol synthetic pathway in Escherichia coli via overexpression of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase and chorismate pyruvate lyase. Phenol titer increases 147-fold after modulating the 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase, chorismate pyruvate lyase, and 4-hydroxybenzoate decarboxylase genes in the chromosome. Tributyrin and dibutyl phthalate are the best two solvents for improving phenol production
synthesis
increase in protocatechuate decarboxylase activity in Escherichia coli through enhanced expression of both protocatechuate decarboxylase AroYand kpdB encoding the B-subunit of 4-hydroxybenzoate decarboxylase. This permits expression of protocatechuate decarboxylase activity at a level approximately 14fold greater than the strain with aroY only. The expression level of AroY increases, apparently as a function of the coexpression of AroY and KpdB
synthesis
-
increase in protocatechuate decarboxylase activity in Escherichia coli through enhanced expression of both protocatechuate decarboxylase AroYand kpdB encoding the B-subunit of 4-hydroxybenzoate decarboxylase. This permits expression of protocatechuate decarboxylase activity at a level approximately 14fold greater than the strain with aroY only. The expression level of AroY increases, apparently as a function of the coexpression of AroY and KpdB
-
synthesis
-
construction of a phenol synthetic pathway in Escherichia coli via overexpression of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase and chorismate pyruvate lyase. Phenol titer increases 147-fold after modulating the 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase, chorismate pyruvate lyase, and 4-hydroxybenzoate decarboxylase genes in the chromosome. Tributyrin and dibutyl phthalate are the best two solvents for improving phenol production
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Grant, D.J.W.; Patel, J.C.
The non-oxidative decarboxylation of p-hydroxybenzoic acid, gentisic acid, protocatechuic acid and gallic acid by Klebsiella aerogenes (Aerobacter aerogenes)
Antonie van Leeuwenhoek
35
325-343
1969
Klebsiella aerogenes
brenda
He, Z.; Wiegel, J.
Purification and characterization of an oxygen-sensitive reversible 4-hydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum
Eur. J. Biochem.
229
77-82
1995
Sedimentibacter hydroxybenzoicus
brenda
Gallert, C.; Winter, J.
Comparison of 4-hydroxybenzoate decarboxylase, and phenol carboxylase activities in cell-free extracts of a defined 4-hydroxybenzoate and phenol-degrading anaerobic consortium
Appl. Microbiol. Biotechnol.
37
119-124
1992
Desulfovibrio sp., Methanospirillum hungatei
-
brenda
Lack, A.; Fuchs, G.
Carboxylation of phenylphosphate by phenol carboxylase, an enzyme system of anaerobic phenol metabolism
J. Bacteriol.
174
3629-3636
1992
Pseudomonas sp., Pseudomonas sp. K172
brenda
Hsu, T.; Lux, M.F.; Drake, H.L.
Expression of an aromatic-dependent decarboxylase which provides growth-essential CO2 equivalents for the acetogenic (wood) pathway of Clostridium thermoaceticum
J. Bacteriol.
172
5901-5907
1990
Moorella thermoacetica
brenda
Lack, A.; Tommasi, I.; Aresta, M.; Fuchs, G.
Catalytic properties of phenol carboxylase. In vitro study of CO2:4hydroxybenzoate isotope exchange reaction
Eur. J. Biochem.
197
473-479
1991
Pseudomonas sp., Pseudomonas sp. K172
brenda
Li, T.; Juteau, P.; Beaudet, R.; Lepine, F.; Villemur, R.; Bisaillon, J.G.
Purification and characterization of a 4-hydroxybenzoate decarboxylase from an anaerobic coculture
Can. J. Microbiol.
46
856-859
2000
uncultured bacterium
brenda
Huang, J.; He, Z.; Wiegel, J.
Cloning, characterization, and expression of a novel gene encoding a reversible 4-hydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum
J. Bacteriol.
181
5119-5122
1999
Sedimentibacter hydroxybenzoicus (Q4R101 and Q9S4M7 and Q4R102), Sedimentibacter hydroxybenzoicus
brenda
Aresta, M.; Dibenedetto, A.
Development of environmentally friendly syntheses: use of enzymes and biomimetic systems for the direct carboxylation of organic substrates
J. Biotechnol.
90
113-128
2002
Thauera aromatica
brenda
Matsui, T.; Yoshida, T.; Hayashi, T.; Nagasawa, T.
Purification, characterization, and gene cloning of 4-hydroxybenzoate decarboxylase of Enterobacter cloacae P240
Arch. Microbiol.
186
21-29
2006
Enterobacter cloacae, Enterobacter cloacae P240
brenda
Liu, J.; Zhang, X.; Zhou, S.; Tao, P.; Liu, J.
Purification and characterization of a 4-hydroxybenzoate decarboxylase from Chlamydophila pneumoniae AR39
Curr. Microbiol.
54
102-107
2007
Chlamydia pneumoniae, Chlamydia pneumoniae AR39
brenda
Lupa, B.; Lyon, D.; Shaw, L.N.; Sieprawska-Lupa, M.; Wiegel, J.
Properties of the reversible nonoxidative vanillate/4-hydroxybenzoate decarboxylase from Bacillus subtilis
Can. J. Microbiol.
54
75-81
2008
Bacillus subtilis (C0H3U9), Bacillus subtilis
brenda
Miao, L.; Li, Q.; Diao, A.; Zhang, X.; Ma, Y.
Construction of a novel phenol synthetic pathway in Escherichia coli through 4-hydroxybenzoate decarboxylation
Appl. Microbiol. Biotechnol.
99
5163-5173
2015
Escherichia coli (AFH12530 and AFH12529 and AFH12528), Escherichia coli, Escherichia coli ATCC 9637 (AFH12530 and AFH12529 and AFH12528)
brenda
Sonoki, T.; Morooka, M.; Sakamoto, K.; Otsuka, Y.; Nakamura, M.; Jellison, J.; Goodell, B.
Enhancement of protocatechuate decarboxylase activity for the effective production of muconate from lignin-related aromatic compounds
J. Biotechnol.
192
71-77
2014
Klebsiella pneumoniae (X5I148), Klebsiella pneumoniae NBRC14940 (X5I148)
brenda
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