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IUBMB Comments The enzyme, from the strict anaerobe Clostridium difficile, can also use (3,4-dihydroxyphenyl)acetate as a substrate, yielding 4-methylcatechol as a product. The enzyme is a glycyl radical enzyme.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
4-hydroxyphenylacetate decarboxylase, 4hpad-ae, p-hydroxyphenylacetate decarboxylase, 4-hpd, 4hpad, p-hpd,
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4-hydroxyphenylacetate decarboxylase
p-hydroxyphenylacetate decarboxylase
4-hydroxyphenylacetate decarboxylase
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4-hydroxyphenylacetate decarboxylase
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4-hydroxyphenylacetate decarboxylase
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CSD
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HPA decarboxylase
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p-hydroxyphenylacetate decarboxylase
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p-hydroxyphenylacetate decarboxylase
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(4-hydroxyphenyl)acetate + H+ = 4-methylphenol + CO2
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decarboxylation
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decarboxylation
Kolbe-type decarboxylation
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4-(hydroxyphenyl)acetate carboxy-lyase (4-methylphenol-forming)
The enzyme, from the strict anaerobe Clostridium difficile, can also use (3,4-dihydroxyphenyl)acetate as a substrate, yielding 4-methylcatechol as a product. The enzyme is a glycyl radical enzyme.
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(3,4-dihydroxyphenyl)acetate + H+
4-methylcatechol + CO2
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
4-hydroxyphenylacetate + H+
4-cresol + CO2
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?
(3,4-dihydroxyphenyl)acetate + H+
4-methylcatechol + CO2
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?
(3,4-dihydroxyphenyl)acetate + H+
4-methylcatechol + CO2
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?
(3,4-dihydroxyphenyl)acetate + H+
4-methylcatechol + CO2
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4-methylcatechol is also named p-cresol
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?
(3,4-dihydroxyphenyl)acetate + H+
4-methylcatechol + CO2
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?
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
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?
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
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?
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
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(4-hydroxyphenyl)acetate is p-cresol
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?
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
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(4-hydroxyphenyl)acetate is p-cresol
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?
(4-hydroxyphenyl)acetate + H+
4-methylphenol + CO2
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(4-hydroxyphenyl)acetate is p-cresol
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?
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4-hydroxyphenylacetate + H+
4-cresol + CO2
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?
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4Fe-4S-center
the gamma-subunit contains two [4Fe-4S] clusters
[4Fe-4S]-center
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the enzyme binds a maximum of two [4Fe-4S]2+/+ clusters
additional information
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indications for an as yet unidentified low molecular weight cofactor that is required for catalytic activity
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Fe
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28-32 iron atoms per native molecule
Fe
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30-32 iron atoms per native molecule
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(3,4-dihydroxyphenyl)acetate
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NaCl
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800 mM, 50% inactivation
O2
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readily and irreversibly inhibited
4-Hydroxyphenylacetamide
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competitive
4-Hydroxyphenylacetamide
competitive inhibitor
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4-hydroxyphenylacetate decarboxylase deficiency
Increased nitric oxide release by neutrophils of a patient with tyrosinemia type III.
Tyrosinemias
Increased nitric oxide release by neutrophils of a patient with tyrosinemia type III.
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0.5
(3,4-dihydroxyphenyl)acetate
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0.358 - 2.8
(4-hydroxyphenyl)acetate
0.388 - 0.41
3,4-Dihydroxyphenylacetate
0.358
(4-hydroxyphenyl)acetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
0.649
(4-hydroxyphenyl)acetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
2.8
(4-hydroxyphenyl)acetate
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-
0.388
3,4-Dihydroxyphenylacetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
0.41
3,4-Dihydroxyphenylacetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
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110 - 135
(4-hydroxyphenyl)acetate
65 - 67
3,4-Dihydroxyphenylacetate
110
(4-hydroxyphenyl)acetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
135
(4-hydroxyphenyl)acetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
65
3,4-Dihydroxyphenylacetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
67
3,4-Dihydroxyphenylacetate
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in 100 mM Tris-HCl, pH 7.5, 40 mM NaCl, 5 mM MgCl2, 5 mM (NH4)2SO4, 5 mM cysteine, 25 mM substrate, and 5 mM dithiothreitol, at 30°C
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0.4
(3,4-dihydroxyphenyl)acetate
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0.48
4-hydroxymandelate
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0.7
4-Hydroxyphenylacetamide
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brenda
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brenda
DSMZ 1296T
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brenda
HpdA protein
SwissProt
brenda
HpdB protein
SwissProt
brenda
HpdC protein
SwissProt
brenda
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brenda
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UniProt
brenda
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brenda
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physiological function
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a truncated version of the activating protein devoid of the ferredoxin-like domain can activate the decarboxylase almost as fast as wild-type, but the generated glycyl radical is short living
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100000
2 * 100000 + 2 * 99500
105000
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alpha,alpha, the smaller unit is a C-terminally truncated form, 1 * 110000 + 1 * 105000, SDS-PAGE
110000
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alpha,alpha, the smaller unit is a C-terminally truncated form, 1 * 110000 + 1 * 105000, SDS-PAGE
36000
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x * 36000, SDS-PAGE
460000
hetero-octameric catalytically competent complex, gel filtration
99500
2 * 100000 + 2 * 99500
440000
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heterotetramer
2 * 100000 + 2 * 99500
octamer
beta4gamma4, small subunit HpdC has a molecular weight of 9598 Da as determined by MALDI TOF MS, the recombinant enzyme is a hetero-octameric catalytically competent complex
dimer
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alpha,alpha, the smaller unit is a C-terminally truncated form, 1 * 110000 + 1 * 105000, SDS-PAGE
dimer
beta2, decarboxylase purified from Clostridium difficile is an almost inactive homo-dimeric protein
heterooctamer
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phosphoprotein
phosphorylation of the small subunit is responsible for th change in oligomeric state from inactive homo-dimeric protein of Clostridium difficile to the recombinant hetero-octameric catalytically competent complex
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hanging drop vapor diffusion method, using 22% (w/v) PEG MME 550, 30 mM MgCl2, 100 mM Tris/HCl pH 7.5-8.4
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6 - 9
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0°C in presence of 1 mM sodium sulfide and 5 mM ammonium sulfate
658599
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30
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half-life: 15 min, in presence of 1 mM sodium sulfide and 5 mM ammonium sulfate
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readily and irreversibly inhibited by O2
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658599
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0°C, 100 mM Tris/HCl, pH 7.5, 5 mM ammonium sulfate, 1 mM magnesium chloride, more than 90% of the activity is recovered after 5 days
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Streptactin-Macroprep column chromatography
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Streptactin-Macroprep column chromatography
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Streptactin-Macroprep column chromatography
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cloning of three genes encoding two subunits of the glycyl-radical enzyme and the activating enzyme, expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli Rosetta (DE3) pLysS cells
expressed in Escherichia coli Rosetta (DE3) pLysS cells
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expressed in Escherichia coli Rosetta (DE3) pLysS cells
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D'Ari, L.; Barker, H.A.
p-Cresol formation by cell-free extracts of Clostridium difficile
Arch. Microbiol.
143
311-312
1985
Clostridioides difficile
brenda
Selmer, T.; Andrei, P.I.
p-Hydroxyphenylacetate decarboxylase from Clostridium difficile. A novel glycyl radical enzyme catalysing the formation of p-cresol
Eur. J. Biochem.
268
1363-1372
2001
Clostridioides difficile
brenda
Andrei, P.I.; Pierik, A.J.; Zauner, S.; Andrei-Selmer, L.C.; Selmer, T.
Subunit composition of the glycyl radical enzyme p-hydroxyphenylacetate decarboxylase. A small subunit, HpdC, is essential for catalytic activity
Eur. J. Biochem.
271
2225-2230
2004
Clostridioides difficile (Q84F14), Clostridioides difficile (Q84F15), Clostridioides difficile (Q84F16), Clostridioides difficile
brenda
Yu, L.; Blaser, M.; Andrei, P.I.; Pierik, A.J.; Selmer, T.
4-hydroxyphenylacetate decarboxylases: Properties of a novel subclass of glycyl radical enzyme systems
Biochemistry
45
9584-9592
2006
Clostridioides difficile, Clostridium scatologenes, Clostridium scatologenes 957
brenda
Martins, B.M.; Blaser, M.; Feliks, M.; Ullmann, G.M.; Buckel, W.; Selmer, T.
Structural basis for a Kolbe-type decarboxylation catalyzed by a glycyl radical enzyme
J. Am. Chem. Soc.
133
14666-14674
2011
Clostridium scatologenes (Q38HX4), Clostridium scatologenes
brenda
Feliks, M.; Martins, B.M.; Ullmann, G.M.
Catalytic mechanism of the glycyl radical enzyme 4-hydroxyphenylacetate decarboxylase from continuum electrostatic and QC/MM calculations
J. Am. Chem. Soc.
135
14574-14585
2013
Clostridium scatologenes
brenda
Selvaraj, B.; Pierik, A.J.; Bill, E.; Martins, B.M.
4-Hydroxyphenylacetate decarboxylase activating enzyme catalyses a classical S-adenosylmethionine reductive cleavage reaction
J. Biol. Inorg. Chem.
18
633-643
2013
Clostridium scatologenes
brenda
Selvaraj, B.; Pierik, A.J.; Bill, E.; Martins, B.M.
The ferredoxin-like domain of the activating enzyme is required for generating a lasting glycyl radical in 4-hydroxyphenylacetate decarboxylase
J. Biol. Inorg. Chem.
19
1317-1326
2014
Clostridioides difficile
brenda
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