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EC Tree
IUBMB Comments 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)
The taxonomic range for the selected organisms is: Escherichia coli The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
acyl-coa hydrolase, them2, type ii thioesterase, them1, acot11, them4, acot13, thioesterase superfamily member 2, te ii, thioesterase 2,
more
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acyl CoA hydrolase
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acyl coenzyme A hydrolase
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acyl coenzyme A thioesterase
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acyl-CoA thioesterase
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brain acyl-CoA hydrolase
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fatty acyl thioesterase I
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HIV-Nef associated acyl coA thioesterase
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hydrolase, acyl coenzyme A
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hydrolase, palmitoyl coenzyme A
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long chain acyl-CoA hydrolase
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long chain acyl-CoA thioesterase
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long chain fatty-acyl-CoA hydrolase
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long chain fatty-acyl-CoA thioesterase
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mitochondrial acyl-CoA thioesterase
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palmitoyl coenzyme A hydrolase
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palmitoyl thioesterase
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palmitoyl-CoA deacylase
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palmitoyl-CoA hydrolase
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palmityl coenzyme A deacylase
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palmityl thioesterase
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palmityl thioesterase I
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palmityl thioesterase II
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very long chain acyl-CoA thioesterase
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hydrolysis of thioester
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hydrolysis of thioester
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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)
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4-Hydroxybenzoyl-CoA + H2O
4-Hydroxybenzoate + CoA
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-
-
?
acetyl-CoA + H2O
CoA + acetate
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-
-
?
beta-methylcrotonyl-CoA + H2O
CoA + beta-methylcrotonate
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-
-
?
isobutyryl-CoA + H2O
CoA + isobutyrate
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-
-
?
lauroyl-CoA + H2O
CoA + laurate
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-
-
?
n-butyryl-CoA + H2O
CoA + n-butyrate
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-
-
?
n-butyryl-pantetheine phosphate + H2O
?
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-
-
?
n-decanoyl-CoA + H2O
CoA + n-decanoate
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-
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?
oleoyl-CoA + H2O
CoA + oleate
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-
-
?
palmitoyl-CoA + H2O
CoA + palmitate
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-
-
?
phenylacetyl-CoA + H2O
CoA + phenylacetate
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-
-
?
3,5-cis-dodecadienoyl-CoA + H2O
CoA + 3,5-cis-dodecadienoic acid
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-
-
?
3,5-cis-tetradecadienoyl-CoA + H2O
CoA + 3,5-cis-tetradecadienoic acid
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-
-
?
3-hydroxytetradecanoyl-CoA + H2O
CoA + 3-hydroxytetradecanoate
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-
-
?
acyl-CoA + H2O
CoA + a carboxylate
arachidoyl-CoA + H2O
CoA + arachidate
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-
-
?
decanoyl-CoA + H2O
CoA + decanoate
dodecanoyl-CoA + H2O
CoA + dodecanoate
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i.e. lauroyl-CoA
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-
?
hexadecanoyl-CoA + H2O
CoA + hexadecanoate
hexanoyl-CoA + H2O
CoA + hexanoate
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-
-
-
?
lauroyl-CoA + H2O
CoA + laurate
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-
-
?
myristoyl-CoA + H2O
CoA + myristate
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-
-
?
octadecanoyl-CoA + H2O
CoA + octadecanoate
oleoyl pantetheine + H2O
oleate + pantetheine
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-
-
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?
oleoyl-CoA + H2O
CoA + oleate
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-
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-
?
oleyl-[acyl-carrier protein] + H2O
oleate + acyl-carrier protein
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?
palmitoleoyl-CoA + H2O
CoA + palmitoleoate
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-
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?
palmitoyl-CoA + H2O
CoA + palmitate
tetradecanoyl-CoA + H2O
CoA + tetradecanoate
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i.e. myristoyl-CoA
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-
?
vaccenoyl-CoA + H2O
CoA + vaccenoate
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cis-isomer
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-
?
additional information
?
-
acyl-CoA + H2O
CoA + a carboxylate
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-
?
acyl-CoA + H2O
CoA + a carboxylate
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-
?
acyl-CoA + H2O
CoA + a carboxylate
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long-chain fatty-acyl-CoA
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-
?
decanoyl-CoA + H2O
CoA + decanoate
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?
decanoyl-CoA + H2O
CoA + decanoate
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?
hexadecanoyl-CoA + H2O
CoA + hexadecanoate
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i.e. palmitoyl-CoA
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-
?
hexadecanoyl-CoA + H2O
CoA + hexadecanoate
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i.e. palmitoyl-CoA
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ir
hexadecanoyl-CoA + H2O
CoA + hexadecanoate
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i.e. palmitoyl-CoA
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ir
octadecanoyl-CoA + H2O
CoA + octadecanoate
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?
octadecanoyl-CoA + H2O
CoA + octadecanoate
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i.e. stearoyl-CoA
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-
?
palmitoyl-CoA + H2O
CoA + palmitate
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?
palmitoyl-CoA + H2O
CoA + palmitate
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?
additional information
?
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the long, medium, and short chain fatty acyl-CoAs are very good substrates as are the small acyl-CoA metabolites
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?
additional information
?
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YciA is responsible for the efficient, indiscriminant CoA-regulated hydrolysis of cellular acyl-CoA thioesters in a wide range of bacteria and hypothesize that this activity may support membrane biogenesis
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?
additional information
?
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decanoyl pantetheine is no substrate
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?
additional information
?
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the physiological role of thioesterase II in Escherichia coli is to prevent the abnormal accumulation of intracellular acyl-coenzyme A
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-
?
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4-Hydroxybenzoyl-CoA + H2O
4-Hydroxybenzoate + CoA
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-
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?
acetyl-CoA + H2O
CoA + acetate
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?
palmitoyl-CoA + H2O
CoA + palmitate
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?
additional information
?
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additional information
?
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the long, medium, and short chain fatty acyl-CoAs are very good substrates as are the small acyl-CoA metabolites
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-
?
additional information
?
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YciA is responsible for the efficient, indiscriminant CoA-regulated hydrolysis of cellular acyl-CoA thioesters in a wide range of bacteria and hypothesize that this activity may support membrane biogenesis
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?
additional information
?
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the physiological role of thioesterase II in Escherichia coli is to prevent the abnormal accumulation of intracellular acyl-coenzyme A
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?
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CoA
strong feedback inhibitor, product inhibition
2,4-dinitrofluorobenzene
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inhibits very slowly
diethyldicarbonate
hydroxylamine reverses
diisopropylfluorophosphate
methylene blue
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photooxidation
PMSF
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less effective than DFP, produces a 27% loss of activity under similar conditions
additional information
no inhibition by iodoacetate
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diisopropylfluorophosphate
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1 mM DFP at 40 min at 25°C produces a 95% inhibition at palmityl thioesterase I
diisopropylfluorophosphate
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at 0.01 mM inhibition of 95% after 40 min.
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0.025
4-hydroxybenzoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.167
acetyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.29
beta-methylcrotonyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.015
isobutyryl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.02
lauroyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.068
n-butyryl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.8
n-butyryl-pantetheine phosphate
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.013
n-decanoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.011
oleoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
33
palmitoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.016
phenylacetyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.0108
3,5-cis-dodecadienoyl-CoA
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0.003
3,5-cis-tetradecadienoyl-CoA
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0.0058
3-hydroxytetradecanoyl-CoA
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0.00013 - 0.006
fatty-acyl-CoA thioester
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-
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0.0062
4-hydroxybenzoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.55
acetyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.1
beta-methylcrotonyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
9.5
isobutyryl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
9.6
lauroyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
6.7
n-butyryl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.082
n-butyryl-pantetheine phosphate
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
17
n-decanoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
13
oleoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
3.7
palmitoyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
9.4
phenylacetyl-CoA
pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
21.6
3,5-cis-dodecadienoyl-CoA
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2 - 3.7
3,5-cis-tetradecadienoyl-CoA
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10.7
3-hydroxytetradecanoyl-CoA
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additional information
additional information
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additional information
additional information
inactive with substrates having acyl chains with fewer than 12 carbon atoms
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additional information
additional information
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inactive with substrates having acyl chains with fewer than 12 carbon atoms
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2000
3,5-cis-dodecadienoyl-CoA
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7900
3,5-cis-tetradecadienoyl-CoA
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1800
3-hydroxytetradecanoyl-CoA
-
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101.3
with 3,5-cis-tetradecadienoyl-CoA
45.5
with 3-hydroxytetradecanoyl-CoA
92.3
with 3,5-cis-dodecadienoyl-CoA
93.8
purified recombinant enzyme
additional information
also comparable activities observed with stearoyl-CoA and oleoyl-CoA
additional information
-
also comparable activities observed with stearoyl-CoA and oleoyl-CoA
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SwissProt
brenda
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brenda
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brenda
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15160
His-tagged YciA protein, determined by electrospray ionization mass spectrometry
122000
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gel filtration, thioesterase I
123000
recombinant enzyme, native PAGE
15000
4 * 15000, crystal structure analysis, SDS-PAGE
20000 - 23000
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gel filtration
30000
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4 * 30000, SDS-PAGE
90000
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gel filtration, palmityl thioesterase II
20000
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20000
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sedimentation velocity
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homohexamer
YciA determined by using equilibrium sedimentation techniques
homotetramer
4 * 15000, crystal structure analysis, SDS-PAGE
tetramer
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4 * 30000, SDS-PAGE
tetramer
4 * 31842-32100, recombinant enzyme, electrospray ionization mass spectroscopy and SDS-PAGE
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hanging drop method, protein solution: 10 mg/ml, 5 mM NH4OH, 2 mM DTT, over equal volume of reservoir solution: 1-2 M NaCl, 0.1 M sodium formate, pH 6.0, 2 mM N,N-dimethyl-dodecylamine oxide-LDAO, few days, X-ray structure determination and analysis
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additional information
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646120
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YciA tends to precipitate at high concentrations
bovine serum albumin stabilizes
bovine serum albumin stabilizes
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bovine serum albumin stabilizes
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Cells are harvested by centrifugation and suspended in lysis buffer, passed through a French press and centrifuged. The supernatant is loaded onto a Ni-NTA agarose column. The column is washed with a buffer containing 50 mM NaH2PO4, 300 mM NaCl, 50 mM imidazole and 1 mM dithiothreitol, and then the YciA is eluted with an imidazole gradient up to 250 mM imidazole. The pooled and concentrated fractions are chromatographed on a size exclusion column using a buffer containing 50 mM NaH2PO4, 50 mM NaCl, 10 mM imidazole and 1 mM dithiothreitol.
20fold, palmityl thioesterase II, palmityl thioesterase I
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ion exchange chromatography (DEAE-cellulose), hydroxylapatite chromatography, hydrophobic interaction chromatography, recombinant protein: immobilized metal ion affinity chromatography (Ni2+), ion exchange chromatography (DEAE-cellulose), hydrophobic interaction chromatography
native wild-type: 8000fold to homogeneity
recombinant wild-type: 4fold to homogeneity
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the gene encoding YciA is amplified by PCR and expressed in Escherichia coli strain BL21 (DE3)
gene tes B, DNA sequence determination and analysis, no sequence similarity between Escherichia coli thioesterase II and the two types of mammalian thioesterases, i.e. the chain-terminating enzymes of de novo fatty acid synthesis
gene tesB, overexpression in the Escherichia coli host strain
heterologous expression of tesB in Pseudomonas putida GPp104
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His-tagged version expressed in Escherichia coli BL21(DE3)
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Barnes jr., E.M.; Wakil, S.J.
Studies on the mechanism of fatty acid synthesis. XIX. Preparation and general properties of palmityl thioesterase
J. Biol. Chem.
243
2955-2962
1968
Columba sp., Escherichia coli
brenda
Bonner, W.M.; Bloch, K.
Purification and properties of fatty acyl thioesterase I from Escherichia coli
J. Biol. Chem.
247
3123-3133
1972
Escherichia coli
brenda
Barnes jr., E.M.
Long-chain fatty acyl thioesterases I and II from Escherichia coli
Methods Enzymol.
35
102-109
1975
Escherichia coli
brenda
Poupon, V.; Begue, B.; Gagnon, J.; Dautry-Varsat, A.; Cerf-Bensussan, N.; Benmerah, A.
Molecular cloning and characterization of MT-ACT48, a novel mitochondrial acyl-CoA thioesterase
J. Biol. Chem.
274
19188-19194
1999
Arabidopsis thaliana, Bacillus subtilis, Caenorhabditis elegans, Drosophila melanogaster, Escherichia coli, Haemophilus influenzae, Helicobacter pylori, Homo sapiens, Mus musculus (Q9R0X4), Oryctolagus cuniculus, Rattus norvegicus
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Naggert, J.; Narasimhan, M.L.; DeVeaux, L.; Cho, H.; Randhawa, Z.I.; Cronan, J.E.; Green, B.N.; Smith, S.
Cloning, sequencing, and characterization of Escherichia coli thioesterase II
J. Biol. Chem.
266
11044-11050
1991
Escherichia coli (P0AGG2)
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Swenson, L.; Green, R.; Smith, S.; Derewenda, Z.S.
Crystallization of thioesterase II from Escherichia coli
J. Mol. Biol.
236
660-662
1994
Escherichia coli (P0AGG2)
brenda
Zheng, Z.; Gong, Q.; Liu, T.; Deng, Y.; Chen, J.C.; Chen, G.Q.
Thioesterase II of Escherichia coli plays an important role in 3-hydroxydecanoic acid production
Appl. Environ. Microbiol.
70
3807-3813
2004
Escherichia coli
brenda
Zhuang, Z.; Song, F.; Zhao, H.; Li, L.; Cao, J.; Eisenstein, E.; Herzberg, O.; Dunaway-Mariano, D.
Divergence of function in the hot dog fold enzyme superfamily: the bacterial thioesterase YciA
Biochemistry
47
2789-2796
2008
Escherichia coli (P0A8Z0), Haemophilus influenzae (P44886)
brenda
Nie, L.; Ren, Y.; Schulz, H.
Identification and characterization of Escherichia coli thioesterase III that functions in fatty acid beta-oxidation
Biochemistry
47
7744-7751
2008
Escherichia coli (P77712), Escherichia coli
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