Information on EC 3.1.2.20 - acyl-CoA hydrolase and Organism(s) Homo sapiens

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This record set is specific for:
Homo sapiens


The expected taxonomic range for this enzyme is: Bacteria, Eukaryota


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
3.1.2.20
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RECOMMENDED NAME
GeneOntology No.
acyl-CoA hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + H2O = CoA + a carboxylate
show the reaction diagram
based on the results of quantum mechanics/molecular mechanics metadynamics techniques simulations, it is demonstrated that hotdog-fold hTHEM2 follows a simple mechanism in which a water molecule directly attacks the carbonyl carbon atom to cleave the thioester bond without requiring an enzyme-substrate covalent intermediate the reaction, providing evidence for the formation of a tetrahedral-like transition state
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of thioester
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
firefly bioluminescence
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jasmonic acid biosynthesis
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3-phenylpropionate degradation
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acetate fermentation
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA hydrolase
Broad specificity for medium- to long-chain acyl-CoA. Insensitive to NAD+ (cf. EC 3.1.2.19 ADP-dependent medium-chain-acyl-CoA hydrolase)
CAS REGISTRY NUMBER
COMMENTARY hide
37270-64-7
EC 3.1.2.2
9025-87-0
EC 3.1.2.20
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-butenoyl-CoA + H2O
CoA + 2-butenoate
show the reaction diagram
-
-
-
?
3,4-dihydroxyphenylacetyl-CoA + H2O
CoA + 3,4-dihydroxyphenylacetate
show the reaction diagram
-
-
-
?
3,5-dihydroxyphenylacetyl-CoA + H2O
CoA + 3,5-dihydroxyphenylacetate
show the reaction diagram
-
-
-
?
3-hydroxy-3-methylglutaryl-CoA + H2O
CoA + 3-hydroxy-3-methylglutarate
show the reaction diagram
-
-
-
?
3-hydroxybenzoyl-CoA + H2O
CoA + 3-hydroxybenzoate
show the reaction diagram
-
-
-
?
3-hydroxyphenylacetyl-CoA + H2O
CoA + 3-hydroxyphenylacetate
show the reaction diagram
-
-
-
?
4-chlorobenzoyl-CoA + H2O
CoA + 4-chlorobenzoate
show the reaction diagram
-
-
-
?
4-hydroxyphenylacetyl-CoA + H2O
CoA + 4-hydroxyphenylacetate
show the reaction diagram
-
-
-
?
acetyl-CoA + H2O
CoA + acetate
show the reaction diagram
acyl-CoA + H2O
CoA + a carboxylate
show the reaction diagram
arachidonoyl-CoA + H2O
CoA + arachidonate
show the reaction diagram
beta-hydroxybutyryl-CoA + H2O
CoA + beta-hydroxybutyrate
show the reaction diagram
-
-
-
?
beta-methylcrotonyl-CoA + H2O
CoA + beta-methylcrotonate
show the reaction diagram
-
-
-
?
crotonyl-CoA + H2O
CoA + crotonate
show the reaction diagram
-
-
-
?
decanoyl-CoA + H2O
CoA + decanoate
show the reaction diagram
-
-
-
?
dodecanoyl-CoA + H2O
CoA + dodecanoate
show the reaction diagram
eicosanoyl-CoA + H2O
CoA + eicosanoic acid
show the reaction diagram
-
-
-
?
gamma-linolenoyl-CoA + H2O
CoA + gamma-linolenoate
show the reaction diagram
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best substrate
-
-
?
glutaryl-CoA + H2O
CoA + glutarate
show the reaction diagram
-
-
-
?
hexadecanoyl-CoA + H2O
CoA + hexadecanoate
show the reaction diagram
hexanoyl-CoA + H2O
CoA + hexanoate
show the reaction diagram
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molecular dynamic simulations are carried out on the X-ray structure 3F5O with hexanoyl-CoA as the substrate
-
-
?
lauroyl-CoA + H2O
CoA + laurate
show the reaction diagram
-
-
-
?
linolenoyl-CoA + H2O
CoA + linolenoate
show the reaction diagram
-
-
-
?
linoleoyl-CoA + H2O
CoA + linolate
show the reaction diagram
-
-
-
?
linoleoyl-CoA + H2O
CoA + linoleate
show the reaction diagram
malonyl-CoA + H2O
CoA + malonate
show the reaction diagram
-
-
-
?
methylmalonyl-CoA + H2O
CoA + methylmalonate
show the reaction diagram
-
-
-
?
myristoyl-CoA + H2O
CoA + myristate
show the reaction diagram
-
-
-
?
myristoyl-CoA + H2O
CoA + myristic acid
show the reaction diagram
-
-
-
?
n-butyryl-CoA + H2O
CoA + n-butanoate
show the reaction diagram
-
-
-
-
?
n-butyryl-CoA + H2O
CoA + n-butyrate
show the reaction diagram
-
-
-
?
n-decanoyl-CoA + H2O
CoA + n-decanoate
show the reaction diagram
-
-
-
?
n-hexanoyl-CoA + H2O
CoA + n-hexanoate
show the reaction diagram
-
-
-
?
n-octanoyl-CoA + H2O
CoA + n-octanoate
show the reaction diagram
-
-
-
?
n-propionyl-CoA + H2O
CoA + n-propionate
show the reaction diagram
-
-
-
?
nafamostat + H2O
6-hydroxynaphthalene-2-carboximidamide + 4-carbamidamidobenzoic acid
show the reaction diagram
-
-
-
-
?
octadecanoyl-CoA + H2O
CoA + octadecanoate
show the reaction diagram
-
-
-
?
oleoyl-CoA + H2O
CoA + oleate
show the reaction diagram
palmitoleoyl-CoA + H2O
CoA + palmitoleate
show the reaction diagram
-
-
-
?
palmitoleoyl-CoA + H2O
CoA + palmitoleoate
show the reaction diagram
-
-
-
?
palmitoyl-CoA + H2O
CoA + palmitate
show the reaction diagram
phenylacetyl-CoA + H2O
CoA + phenylacetate
show the reaction diagram
-
-
-
?
stearoyl-CoA + H2O
CoA + stearate
show the reaction diagram
succinyl-CoA + H2O
CoA + succinate
show the reaction diagram
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-
-
?
tetradecanoyl-CoA + H2O
CoA + tetradecanoate
show the reaction diagram
-
-
-
?
tiglyl-CoA + H2O
CoA + (2E)-2-methylbut-2-enoate
show the reaction diagram
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-
-
?
vaccenoyl-CoA + H2O
CoA + vaccenoate
show the reaction diagram
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-
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
arachidonoyl-CoA + H2O
CoA + arachidonate
show the reaction diagram
palmitoyl-CoA + H2O
CoA + palmitate
show the reaction diagram
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-
-
-
?
additional information
?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
desulfoCoA
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Nafamostat
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competitive inhibition of palmitoyl-CoA hydrolytic activity
NGDA
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isozymes CTE-I and MTE-I
p-chloromercuribenzoic acid
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palmitoyl-CoA
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0.1 mM, 67% inhibition of nafamostat
phenylacetylmethyl-CoA
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phenylmethylsulfonyl fluoride
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0.1 mM, 43% inhibition of nafamostat hydrolysis
undecan-2-one-CoA
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additional information
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no inhibition by acetyl-CoA, diisopropyl fluorophosphate and bis(p-nitrophenyl)phosphate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ACTH
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bovine serum albumin
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linoleic acid
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both conjugated and gamma-linoleic acid, increase activity
additional information
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no stimulation of activity by docosahexaenoic and eisosapentaenoic acids
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.22
2-butenoyl-CoA
wild-type protein, pH7.5, 25°C
0.01
3,4-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.025
3,5-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
2.9
3-hydroxy-3-methylglutaryl-CoA
wild-type protein, pH7.5, 25°C
0.032
3-hydroxybenzoyl-CoA
wild-type protein, pH7.5, 25°C
0.026 - 0.9
3-hydroxyphenylacetyl-CoA
0.13
4-chlorobenzoyl-CoA
wild-type protein, pH7.5, 25°C
0.049
4-hydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.29
acetyl-CoA
wild-type protein, pH7.5, 25°C
0.002 - 0.02
Arachidonoyl-CoA
0.0092
arachidoyl-CoA
pH 7.4, 30°C
0.11
beta-hydroxybutyryl-CoA
wild-type protein, pH7.5, 25°C
0.12
beta-methylcrotonyl-CoA
wild-type protein, pH7.5, 25°C
0.18
crotonyl-CoA
wild-type protein, pH7.5, 25°C
0.0076
Dodecanoyl-CoA
pH 7.4, 30°C
0.67
glutaryl-CoA
wild-type protein, pH7.5, 25°C
0.0064
hexadecanoyl-CoA
pH 7.4, 30°C
0.0099
lauroyl-CoA
wild-type protein, pH7.5, 25°C
0.0154
Linolenoyl-CoA
pH 7.5, 37°C, wild-type
0.0042 - 0.31
linoleoyl-CoA
0.28
malonyl-CoA
wild-type protein, pH7.5, 25°C
0.21
methylmalonyl-CoA
wild-type protein, pH7.5, 25°C
0.005 - 0.009
myristoyl-CoA
0.6
n-Butyryl-CoA
wild-type protein, pH7.5, 25°C
0.0049
n-decanoyl-CoA
wild-type protein, pH7.5, 25°C
0.07
n-Hexanoyl-CoA
wild-type protein, pH7.5, 25°C
0.026
n-Octanoyl-CoA
wild-type protein, pH7.5, 25°C
0.19
n-propionyl-CoA
wild-type protein, pH7.5, 25°C
0.014
Octanoyl-CoA
pH 7.4, 30°C
0.0088 - 0.009
oleoyl-CoA
0.009 - 0.026
palmitoleoyl-CoA
0.0024 - 0.016
palmitoyl-CoA
0.24
phenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.0042 - 0.02
stearoyl-CoA
0.014
succinyl-CoA
-
0.25
tiglyl-CoA
wild-type protein, pH7.5, 25°C
0.0029
Vaccenoyl-CoA
pH 7.5, 37°C, wild-type
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014
2-butenoyl-CoA
wild-type protein, pH7.5, 25°C
0.19
3,4-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.19
3,5-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.079
3-hydroxy-3-methylglutaryl-CoA
wild-type protein, pH7.5, 25°C
0.011
3-hydroxybenzoyl-CoA
wild-type protein, pH7.5, 25°C
0.007 - 1.4
3-hydroxyphenylacetyl-CoA
0.0032
4-chlorobenzoyl-CoA
wild-type protein, pH7.5, 25°C
0.14
4-hydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.054
acetyl-CoA
wild-type protein, pH7.5, 25°C
0.022 - 1.4
Arachidonoyl-CoA
0.18
beta-hydroxybutyryl-CoA
wild-type protein, pH7.5, 25°C
0.023
beta-methylcrotonyl-CoA
wild-type protein, pH7.5, 25°C
0.0076
crotonyl-CoA
wild-type protein, pH7.5, 25°C
0.05
glutaryl-CoA
wild-type protein, pH7.5, 25°C
0.019
lauroyl-CoA
wild-type protein, pH7.5, 25°C
13.3
Linolenoyl-CoA
pH 7.5, 37°C, wild-type
0.017 - 12.2
linoleoyl-CoA
0.066
malonyl-CoA
wild-type protein, pH7.5, 25°C
0.083
methylmalonyl-CoA
wild-type protein, pH7.5, 25°C
0.02 - 19.7
myristoyl-CoA
0.047
n-Butyryl-CoA
wild-type protein, pH7.5, 25°C
0.016
n-decanoyl-CoA
wild-type protein, pH7.5, 25°C
0.022
n-Hexanoyl-CoA
wild-type protein, pH7.5, 25°C
0.0047
n-Octanoyl-CoA
wild-type protein, pH7.5, 25°C
0.036
n-propionyl-CoA
wild-type protein, pH7.5, 25°C
0.011
oleoyl-CoA
wild-type protein, pH7.5, 25°C
0.017 - 11.5
palmitoleoyl-CoA
0.0044 - 16.6
palmitoyl-CoA
0.084
phenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.011 - 1.2
stearoyl-CoA
0.02
tiglyl-CoA
wild-type protein, pH7.5, 25°C
1.8
Vaccenoyl-CoA
pH 7.5, 37°C, wild-type
additional information
additional information
no activity observed with 4-hydroxybenzoyl-CoA, lauroyl-acyl carrier protein, myristoyl-acyl carrier protein, palmitoyl-acyl carrier protein, octanoyl-acyl carrier protein, oleoyl-acyl carrier protein and acylated peptide N-acetyl-Gly-Ala-Cys-S-palmitoyl, turnover number of mutant protein D65A below 0.00001 s-1 for 3-hydroxyphenylacetyl-CoA
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.064
2-butenoyl-CoA
wild-type protein, pH7.5, 25°C
18
3,4-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
7.9
3,5-dihydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.027
3-hydroxy-3-methylglutaryl-CoA
wild-type protein, pH7.5, 25°C
0.35
3-hydroxybenzoyl-CoA
wild-type protein, pH7.5, 25°C
0.023 - 35
3-hydroxyphenylacetyl-CoA
0.025
4-chlorobenzoyl-CoA
wild-type protein, pH7.5, 25°C
2.9
4-hydroxyphenylacetyl-CoA
wild-type protein, pH7.5, 25°C
0.18
acetyl-CoA
wild-type protein, pH7.5, 25°C
1.1 - 73
Arachidonoyl-CoA
1.6
beta-hydroxybutyryl-CoA
wild-type protein, pH7.5, 25°C
0.19
beta-methylcrotonyl-CoA
wild-type protein, pH7.5, 25°C
0.47
crotonyl-CoA
wild-type protein, pH7.5, 25°C
0.75
glutaryl-CoA
wild-type protein, pH7.5, 25°C
1.9
lauroyl-CoA
wild-type protein, pH7.5, 25°C
860
Linolenoyl-CoA
pH 7.5, 37°C, wild-type
0.054 - 2900
linoleoyl-CoA
0.24
malonyl-CoA
wild-type protein, pH7.5, 25°C
0.39
methylmalonyl-CoA
wild-type protein, pH7.5, 25°C
4 - 2300
myristoyl-CoA
0.078
n-Butyryl-CoA
wild-type protein, pH7.5, 25°C
3.3
n-decanoyl-CoA
wild-type protein, pH7.5, 25°C
0.31
n-Hexanoyl-CoA
wild-type protein, pH7.5, 25°C
0.18
n-Octanoyl-CoA
wild-type protein, pH7.5, 25°C
0.19
n-propionyl-CoA
wild-type protein, pH7.5, 25°C
1.3
oleoyl-CoA
wild-type protein, pH7.5, 25°C
1.9 - 430
palmitoleoyl-CoA
0.28 - 6900
palmitoyl-CoA
0.35
phenylacetyl-CoA
wild-type protein, pH7.5, 25°C
5.5 - 290
stearoyl-CoA
0.082
tiglyl-CoA
wild-type protein, pH7.5, 25°C
540
Vaccenoyl-CoA
pH 7.5, 37°C, wild-type
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.009
desulfoCoA
-
0.164
Nafamostat
-
-
0.5
phenylacetylmethyl-CoA
-
0.003 - 0.0033
undecan-2-one-CoA
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
198
purified native enzyme, substrate palmitoyl-CoA
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
30
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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isozyme CTE-I
Manually annotated by BRENDA team
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i.e. BeWo cells; placental
Manually annotated by BRENDA team
weak expression
Manually annotated by BRENDA team
strongest expression in liver and kidney
Manually annotated by BRENDA team
weak expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24000
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gel filtration
35000
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x * 35000, SDS-PAGE
36000
x * 36000, SDS-PAGE
43000
n * 43000, enzyme is a dimer or a trimer of MW 100 kDa, SDS-PAGE
70000
-
gel filtration
100000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
gel filtration
homodimer
gel filtration
homotetramer
oligomer
n * 43000, enzyme is a dimer or a trimer of MW 100 kDa, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
enzyme forms homodimers in crystals. DELTA1-34 deletion mutant is crystallized to 1.45 A resolution; enzyme forms homodimers in crystals. DELTA1-34 deletion mutant is crystallized to 1.6 A resolution
hanging drop vapor diffusion method
sitting-drop vapor diffusion method
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
glycerol and palmitoyl-CoA stabilize
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, 1 week
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
22fold
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from brain
immobilized metal ion affinity chromatography (Ni2+), gelfiltration
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recombinant as His-tagged or GST-fusion protein from bacteria
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recombinant GST-tagged isozymes CTE-I and MTE-I, this one also His-tagged, from Escherichia coli, to homogeneity
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using Ni-NTA chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
analysis carried out with a deletion mutant lacking the first 35 amino acids DELTA1-34. Expressed in Escherichia coli as a His-tagged fusion protein
DNA sequence determination and analysis, chromosome mapping 1p36.2, expression in Escherichia coli
DNA sequence determination and analysis, subcloning in Escherichia coli, expression fused to maltose-binding-protein in Escherichia coli strain DH10B
expression as His-tagged enzyme in Escherichia coli and as GST-fusion protein in bacteria
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expression in Escherichia coli
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expression in Escherichia coli; isozymes MTE-I, His-tagged, and CTE-I, both GST-fusion proteins
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His-tagged version expressed in Escherichia coli BL21(DE3)
His-taggend version of residue 46-483 expressed in Escherichia coli BL21 (DE3 Rosetta)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D167A
D167 is a key catalytic residue. D167A no longer displays catalytic activity
D65A
active site residue
D65E
active site residue
D65N
active site residue
DELTA1-37
mutant lacking the first 37 N-terminal amino acids is excluded from mitochondria
H134A
reduction in catalytic efficiency
H137A
conserved among vertebrate homologues
H56A
active site residue
K136A
relatively small perturbation in catalytic efficiency
N50A
active site residue
S83A
active site residue
T69A
active site residue