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Information on EC 3.1.1.56 - methylumbelliferyl-acetate deacetylase
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3.1.1.56 methylumbelliferyl-acetate deacetylaseIUBMB Comments
Acts on short-chain acyl esters of 4-methylumbelliferone, but not on naphthyl, indoxyl or thiocholine esters.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
ested, serine thioesterase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EsteD
esterase D
S-formylglutathione hydrolase
esterase D
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
4-methylumbelliferyl-acetate acylhydrolase
Acts on short-chain acyl esters of 4-methylumbelliferone, but not on naphthyl, indoxyl or thiocholine esters.
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CAS REGISTRY NUMBER
COMMENTARY
83380-83-0
-
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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
diethyl 4-nitrophenyl phosphate + H2O
4-nitrophenol + diethyl phosphate
-
-
-
-
?
dimethyl 4-nitrophenyl phosphate + H2O
4-nitrophenol + dimethyl phosphate
-
-
-
-
?
p-nitrophenyl butyrate + H2O
p-nitrophenol + butyrate
-
22°C, pH 7.4, no substrate inhibition below 1 mM p-nitrophenyl butyrate
quantification at 405 nm
-
?
S-lactoylglutathione + H2O
lactone + glutathione
-
-
quantification at 240 nm
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
-
phenotype Es-B, but not Es-D
-
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
-
phenotype Es-B, but not Es-D
-
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
-
phenotype Es-B, but not Es-D
-
-
?
1-naphthyl butyrate + H2O
1-naphthol + butyrate
-
phenotype Es-B, but not Es-D
-
-
?
1-naphthyl butyrate + H2O
1-naphthol + butyrate
-
phenotype Es-B, but not Es-D
-
-
?
1-naphthyl butyrate + H2O
1-naphthol + butyrate
-
phenotype Es-B, but not Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
esterase D is identical to sialic acid-specific O-acetylesterase, which appears to be involved in the recycling of O-acetylated sialic acid molecules
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
hydrolysis via formation of covalent, negatively charged enzyme-substrate tetrahydral intermediate: nucleophilic attack of S149 on carbonyl moiety after activation by H260, intermediate stabilized in oxyanion hole by M150 and L54, H260 stabilized by D226, release of alcohol followed by nucleophilic attack of water molecule at the acidic moiety and release of acetate
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
2 min, 25°C, pH 7.4
reaction stop by citric acid, quantification at 460 nm
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
-
?
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
-
two electrophoretic phenotypes: Es-B and Es-D
-
-
?
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
-
two electrophoretic phenotypes: Es-B and Es-D
-
-
?
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
-
two electrophoretic phenotypes: Es-B and Es-D
-
-
?
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
-
-
-
-
?
4-methylumbelliferyl propionate + H2O
4-methylumbelliferone + propionate
-
Es-D
-
-
?
4-methylumbelliferyl propionate + H2O
4-methylumbelliferone + propionate
-
Es-D
-
-
?
4-methylumbelliferyl propionate + H2O
4-methylumbelliferone + propionate
-
Es-D
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
-
22°C, pH 7.4, no substrate inhibition below 5 mM p-nitrophenyl acetate
quantification at 405 nm
-
?
additional information
?
-
-
acts on short chain acyl esters of 4-methylumbelliferone, but not on naphthyl, indoxyl or thiocholine esters
-
-
?
additional information
?
-
-
the enzyme catalyses the hydrolysis of S-formylglutathione, a role in formaldehyde detoxification is possible
-
-
?
additional information
?
-
-
preference of p-nitrophenyl acetate over p-nitrophenyl butyrate reversed upon mutation W197I
-
-
?
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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
?
-
-
the enzyme catalyses the hydrolysis of S-formylglutathione, a role in formaldehyde detoxification is possible
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
phenotype Es-D
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
esterase D is identical to sialic acid-specific O-acetylesterase, which appears to be involved in the recycling of O-acetylated sialic acid molecules
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
hydrolysis via formation of covalent, negatively charged enzyme-substrate tetrahydral intermediate: nucleophilic attack of S149 on carbonyl moiety after activation by H260, intermediate stabilized in oxyanion hole by M150 and L54, H260 stabilized by D226, release of alcohol followed by nucleophilic attack of water molecule at the acidic moiety and release of acetate
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
-
-
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Diethyl p-nitrophenyl phosphate
-
at high concentration (22°C, pH 7.4), resistance to diethyl p-nitrophenyl phosphate (also paraoxon, an organophosphorus inhibitor) is mediated by W197
dimethyl p-nitrophenyl phosphate
-
also methyl paraoxon (an organophosphorus inhibitor), resistance not due to hydrolysis of inhibitor
additional information
-
relatively insensitive to: 4-nitrophenyl phosphate and acetozolamide
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cystamine
-
inhibits Es-D activity and changes the electrophoretic mobility of Es-B
cystamine
-
inhibits Es-D activity and changes the electrophoretic mobility of Es-B
cystamine
-
inhibits Es-D activity and changes the electrophoretic mobility of Es-B
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Uveitis
Proteomic surveillance of retinal autoantigens in endogenous uveitis: implication of esterase D and brain-type creatine kinase as novel autoantigens.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.23
p-nitrophenyl acetate
-
mutant L58F/W197I, Lineweaver-Burke extrapolation
0.32
p-nitrophenyl acetate
-
mutant C60S, after removal of beta-mercaptoethanol
additional information
p-nitrophenyl butyrate
-
below 0.2 mM, mutant L58F/W197I, Lineweaver-Burke extrapolation
additional information
S-Lactoylglutathione
-
above 1.25 mM, wild-type
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0067
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, wild-type, 22°C
0.1
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, mutant W197H, 22°C
0.187
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, mutant W197I, 22°C
0.317
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60Q, 22°C
0.333
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60H, 22°C
0.733
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60R, 22°C
0.767
diethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60K, 22°C
0.00483
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, wild-type, 22°C
0.217
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, mutant M162H, 22°C
0.24
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60Q, 22°C
0.417
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, mutant W197I, 22°C
0.53
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60H, 22°C
0.637
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60K, 22°C
0.8
dimethyl 4-nitrophenyl phosphate
-
phosphorylation rate, double mutant W197I/C60R, 22°C
0.0055
p-nitrophenyl acetate
-
mutant L58F/W197I, Lineweaver-Burke extrapolation
1.583
p-nitrophenyl acetate
-
mutant C60S, after removal of beta-mercaptoethanol
additional information
dimethyl p-nitrophenyl phosphate
-
no detectable phosphorylation rate, double mutant W197I/C60S, 22°C
additional information
p-nitrophenyl acetate
-
mutant C60H/W197I, catalytic efficiency kcat/KM: 260 +/-20 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60K/W197I, catalytic efficiency kcat/KM: 390 +/-30 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60Q/W197I, catalytic efficiency kcat/KM: 320 +/-30 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60R/W197I, catalytic efficiency kcat/KM: 1500 +/-200 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60S, after removal of beta-mercaptoethanol, catalytic efficiency kcat/KM: 300 +/-60 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60S, catalytic efficiency kcat/KM: 480 +/-80 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant C60S/W197I, catalytic efficiency kcat/KM: 330 +/-20 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant L58F/W197I, Lineweaver-Burke extrapolation, catalytic efficiency kcat/KM: 1.5 +/-0.5 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant M162H, catalytic efficiency kcat/KM: 7 +/-3 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant M162H/C60S/W197I, catalytic efficiency kcat/KM: 0.7 +/-0.2 1/mM/min
additional information
p-nitrophenyl acetate
-
mutant W197I, catalytic efficiency kcat/KM: 1200 +/-100 1/mM/min
additional information
p-nitrophenyl acetate
-
wild-type, catalytic efficiency kcat/KM: 270 +/-50 1/mM/min
additional information
p-nitrophenyl butyrate
-
maximal 0.0165/sec, mutant L58F/W197I, Lineweaver-Burke extrapolation
additional information
p-nitrophenyl butyrate
-
mutant C60H/W197I, catalytic efficiency kcat/KM: 1700 +/-300 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant C60K/W197I, catalytic efficiency kcat/KM: 2500 +/-1600 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant C60Q/W197I, catalytic efficiency kcat/KM: 8000 +/-1000 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant C60R/W197I, catalytic efficiency kcat/KM: 1400 +/-200 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant C60S, catalytic efficiency kcat/KM: 50 +/-20 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant C60S/W197I, catalytic efficiency kcat/KM: 6200 +/-700 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant L58F/W197I, Lineweaver-Burke extrapolation, catalytic efficiency kcat/KM: below 5 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant M162H, catalytic efficiency kcat/KM: 1.4 +/-0.5 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant M162H/C60S/W197I, catalytic efficiency kcat/KM: 20 +/-5 1/mM/min
additional information
p-nitrophenyl butyrate
-
mutant W197I, catalytic efficiency kcat/KM: 2900 +/-700 1/mM/min
additional information
p-nitrophenyl butyrate
-
wild-type, catalytic efficiency kcat/KM: 130 +/-30 1/mM/min
additional information
S-Lactoylglutathione
-
mutant C60S/W197I, catalytic efficiency kcat/KM: 1000 +/-700 1/mM/min
additional information
S-Lactoylglutathione
-
mutant W197I, catalytic efficiency kcat/KM: 2000 +/-1000 1/mM/min
additional information
S-Lactoylglutathione
-
wild-type, activity not twice above background (spontaneous hydrolysis)
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
Diethyl p-nitrophenyl phosphate
-
double mutant W197I/C60H, spontaneous dephosphorylation below 1%, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
double mutant W197I/C60K, spontaneous dephosphorylation below 2%, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
double mutant W197I/C60Q, spontaneous dephosphorylation below 5%, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
double mutant W197I/C60R, spontaneous dephosphorylation below 1%, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 0.38 +/-0.05 mM, mutant W197H, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 0.6 +/-0.2 mM, double mutant W197I/C60K, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 0.7 +/-0.1 mM, mutant W197I, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 0.8 +/-0.6 mM, double mutant W197I/C60H, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 1.04 +/-0.09 mM, double mutant W197I/C60R, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 1.1 +/-0.3 mM, double mutant W197I/C60Q, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 29.9 +/-9 mM, wild-type, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
mutant W197I, spontaneous dephosphorylation below 4%, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 0.014 +/-0.005 mM/h, wild-type, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 16 +/-2 mM/h, mutants W197I and W197H, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 17 +/-5 mM/h, double mutant W197I/C60Q, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 30 +/-20 mM/h, double mutant W197I/C60H, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 42 +/-4 mM/h, double mutant W197I/C60R, 22°C
additional information
Diethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 80 +/-30 mM/h, double mutant W197I/C60K, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
double mutant W197I/C60H, spontaneous dephosphorylation rate: 0.09 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
double mutant W197I/C60K, spontaneous dephosphorylation rate: 0.24 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
double mutant W197I/C60Q, spontaneous dephosphorylation rate: 0.25 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
double mutant W197I/C60R, spontaneous dephosphorylation rate: 0.15 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
double mutant W197I/C60S, spontaneous dephosphorylation rate: 0.17 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 2.3 +/-0.3 mM, double mutant W197I/C60K, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 2.5 +/-0.9 mM, wild-type, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 200 +/-100 mM, mutant M162H, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 3.5 +/-0.8 mM, mutant W197I, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 4 +/-2 mM, double mutant W197I/C60H, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 5 +/-1 mM, double mutant W197I/C60Q, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
half maximal phosphorylation at inhibitor concentration of 5 +/-1 mM, double mutant W197I/C60R, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
mutant M162H, spontaneous dephosphorylation rate: 0.20 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
mutant W197I, spontaneous dephosphorylation rate: 0.4 1/h, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 0.07 +/-0.05 mM/h, mutant M162H, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 0.12 +/-0.04 mM/h, wild-type, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 10 +/-2 mM/h, double mutant W197I/C60R, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 12.9 +/-0.6 mM/h, double mutant W197I/C60Q, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 17 +/-2 mM/h, double mutant W197I/C60K, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 7 +/-2 mM/h, mutant W197I, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
rate of enzyme-inhibitor complex formation in absence of substrate: 8 +/-4 mM/h, double mutant W197I/C60H, 22°C
additional information
dimethyl p-nitrophenyl phosphate
-
wild-type, spontaneous dephosphorylation rate: 0.8 1/h, 22°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information