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EC Tree
IUBMB Comments Not identical with EC 2.3.1.13, glycine N-acyltransferase or EC 2.3.1.68, glutamine N-acyltransferase
The enzyme appears in viruses and cellular organisms
Synonyms
benzoyl-coa:glycine n-acyltransferase, aralkyl-coa:glycine n-acyltransferase,
more
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aralkyl-CoA:glycine N-acyltransferase
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benzoyl CoA-amino acid N-acyltransferase
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benzoyl-CoA:glycine N-acyltransferase
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benzoyltransferase, glycine
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glycine N-acyltransferase
GlyAT
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glycine N-acyltransferase
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glycine N-acyltransferase
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benzoyl-CoA + glycine = CoA + hippurate
benzoyl-CoA + glycine = CoA + hippurate
sequential reaction mechanism in which the acyl-CoA substrate adds to the enzyme first, glycine adds before CoA leaves and the peptide product dissociates last
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benzoyl-CoA + glycine = CoA + hippurate
sequential two-substrate mechanism
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benzoyl-CoA + glycine = CoA + hippurate
residue Glu226 functions to deprotonate glycine, facilitating nucleophilic attack on the acyl-CoA substrate
benzoyl-CoA + glycine = CoA + hippurate
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Acyl group transfer
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benzoyl-CoA:glycine N-benzoyltransferase
Not identical with EC 2.3.1.13, glycine N-acyltransferase or EC 2.3.1.68, glutamine N-acyltransferase
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3-methylcrotonyl-CoA + glycine
CoA + N-3-methylcrotonylglycine
4-aminobenzoyl-CoA + glycine
CoA + N-(4-aminobenzoyl)glycine
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-
-
?
acetyl-CoA + glycine
CoA + N-acetylglycine
benzoyl-CoA + alanine
CoA + N-benzoylalanine
benzoyl-CoA + glutaminic acid
CoA + N-benzoylglutamic acid
benzoyl-CoA + glycine
CoA + hippurate
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-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
benzoyl-CoA + glycine ethyl ester
CoA + N-benzoylglycine ethyl ester
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-
-
?
benzoyl-CoA + glycine methyl ester
CoA + N-benzoylglycine methyl ester
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-
-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
benzoyl-CoA + L-glutamine
CoA + N-benzoyl-L-glutamine
24% of the rate with glycine and benzoyl-CoA
-
-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoylglutamine
benzoyl-CoA + serine
CoA + N-benzoylserine
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
indoleacetyl-CoA + glycine
CoA + N-indoleacetylglycine
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-
-
-
?
isobutyryl-CoA + glycine
CoA + N-isobutyrylglycine
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
methylmalonyl-CoA + glycine
CoA + N-methylmalonylglycine
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-
-
-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
naphthylacetyl-CoA + glycine
CoA + N-naphthylacetylglycine
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-
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?
phenylacetyl-CoA + glycine
CoA + N-phenylacetylglycine
phenylacetyl-CoA + L-glutamine
CoA + N-phenylacetyl-L-glutamine
20% of the rate with glycine and benzoyl-CoA
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-
?
propionyl-CoA + glycine
CoA + N-propionylglycine
salicyl-CoA + glycine
CoA + salicyluric acid
tiglyl-CoA + glycine
CoA + N-tiglylglycine
additional information
?
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3-methylcrotonyl-CoA + glycine
CoA + N-3-methylcrotonylglycine
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-
-
-
?
3-methylcrotonyl-CoA + glycine
CoA + N-3-methylcrotonylglycine
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32% of the activity with benzoyl-CoA
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-
?
acetyl-CoA + glycine
CoA + N-acetylglycine
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?
acetyl-CoA + glycine
CoA + N-acetylglycine
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32% of the activity with benzoyl-CoA
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-
?
benzoyl-CoA + alanine
CoA + N-benzoylalanine
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0.23% of the activity with Gly
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?
benzoyl-CoA + alanine
CoA + N-benzoylalanine
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5% of the activity with Gly
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-
?
benzoyl-CoA + glutaminic acid
CoA + N-benzoylglutamic acid
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0.06% of the activity with Gly
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-
?
benzoyl-CoA + glutaminic acid
CoA + N-benzoylglutamic acid
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-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
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?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
best substrates are benzoyl-CoA as an acyl donor and glycine as acyl acceptor
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?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
glycine serves as the best amino donor substrate, and benzoyl-CoA serves as the best the amino acceptor substrate
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?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
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?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
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-
-
-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
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weak activity
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-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
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1.88% of the activity with Gly
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-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoylglutamine
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weak activity
-
-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoylglutamine
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0.52% of the activity with Gly
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-
?
benzoyl-CoA + serine
CoA + N-benzoylserine
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0.03% of the activity with Gly
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?
benzoyl-CoA + serine
CoA + N-benzoylserine
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0.88% of the activity with Gly
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?
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
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3.9% of the activity with benzoyl-CoA
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?
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
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9.5% of the activity with benzoyl-CoA
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?
isobutyryl-CoA + glycine
CoA + N-isobutyrylglycine
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-
-
?
isobutyryl-CoA + glycine
CoA + N-isobutyrylglycine
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25% of the activity with benzoyl-CoA
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?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
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?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
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8.4% of the activity with benzoyl-CoA
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-
?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
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103% of the activity with benzoyl-CoA
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?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
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9.1% of the activity with benzoyl-CoA
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?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
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-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
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19% of the activity with benzoyl-CoA
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?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
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223% of the activity with benzoyl-CoA
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?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
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28% of the activity with benzoyl-CoA
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?
phenylacetyl-CoA + glycine
CoA + N-phenylacetylglycine
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?
phenylacetyl-CoA + glycine
CoA + N-phenylacetylglycine
22% of the rate with glycine and benzoyl-CoA
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?
propionyl-CoA + glycine
CoA + N-propionylglycine
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?
propionyl-CoA + glycine
CoA + N-propionylglycine
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53% of the activity with benzoyl-CoA
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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35% of the activity with benzoyl-CoA
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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15% of the activity with benzoyl-CoA
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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22% of the activity with benzoyl-CoA
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?
tiglyl-CoA + glycine
CoA + N-tiglylglycine
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?
tiglyl-CoA + glycine
CoA + N-tiglylglycine
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115% of the activity with benzoyl-CoA
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?
additional information
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enzyme also shows glycine N-acyltransferase activity, reaction of EC 2.3.1.13. Amino acceptor substrate preference in decreasing order is benzoyl-CoA, butyryl-CoA, hexanoyl-CoA, acetyl-CoA
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?
additional information
?
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enzyme synthesis is induced in response to cholestasis
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?
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benzoyl-CoA + glycine
CoA + hippurate
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?
additional information
?
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enzyme synthesis is induced in response to cholestasis
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?
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CoA
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in absence of KCl, 0.1 mM CoA inhibits activity over 40% irrespective of the concentration of glycine. In presence of KCl, CoA inhibits activity only slightly, less than 10%. In presence of potassium phosphate the inhibition is reduced to less than 2%. 2.5 mM, almost complete inhibition of salt-free enzyme
p-hydroxymercuribenzoate
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1 mM, 24°C, 90% inhibition after 40 min
hippuric acid
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competitive with respect to benzoyl-CoA
K+
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200 mM KCl, 44% inhibition
K+
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K+ is a competitive inhibitor for benzoyl-coenzyme A, not a competitive inhibitor for salicylyl-CoA, K+ increases Km-value for glycine 10fold
K+
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100 mM, 50% inhibition
Mg2+
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100 mM MgCl2, 90% inhibition
Ni2+
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10 mM NiCl2, 98% inhibition
Zn2+
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1 mM ZnCl2, 13% inhibition
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9.7
glycine ethyl ester
pH 8.0, temperature not specified in the publication
29
Glycine methyl ester
pH 8.0, temperature not specified in the publication
360
methylmalonyl-CoA
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7.6
salicyl-CoA
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reaction with salicylyl-CoA
997
Ala
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0.0094
benzoyl-CoA
pH 8.0, temperature not specified in the publication
0.016
benzoyl-CoA
wild-type, pH 8.0, 30°C
0.016
benzoyl-CoA
recombinant wild-type, pH 8.0, 30°C
0.018
benzoyl-CoA
mutant E226Q, pH 8.0, 30°C
0.021
benzoyl-CoA
mutant K16N, pH 8.0, 37°C
0.024
benzoyl-CoA
wild-type, pH 8.0, 37°C
0.028
benzoyl-CoA
mutant S17T, pH 8.0, 37°C
0.038
benzoyl-CoA
mutant N156S, pH 8.0, 37°C
0.049
benzoyl-CoA
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purified recombinant S156 haplotype, apparent value, random bi-bi (sequential) mechanism, at pH 8.0, temperature not specified in the publication
0.053
benzoyl-CoA
mutant F168L, pH 8.0, 37°C
0.053
benzoyl-CoA
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purified recombinant S156 haplotype, apparent value, ping-pong bi-bi (non-sequential) mechanism, at pH 8.0, temperature not specified in the publication
0.06
benzoyl-CoA
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purified recombinant S156 haplotype, apparent value, ordered bi-bi (sequential) mechanism, at pH 8.0, temperature not specified in the publication
0.071
benzoyl-CoA
mutant R131H, pH 8.0, 37°C
13
benzoyl-CoA
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reaction with Gly
15.2
benzoyl-CoA
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reaction with Ala
41
benzoyl-CoA
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reaction with Ala
45
benzoyl-CoA
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reaction with L-Asn or L-Gln
105
benzoyl-CoA
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reaction with Gln
157
benzoyl-CoA
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reaction with Asn
160
benzoyl-CoA
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reaction with Gly
998
benzoyl-CoA
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reaction with Glu
6
Gly
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reaction with benzoyl-CoA
0.0016
glycine
wild-type, pH 8.0, 30°C
0.002
glycine
recombinant wild-type, pH 8.0, 30°C
0.007
glycine
mutant E226Q, pH 8.0, 30°C
2
glycine
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reaction with benzoyl-CoA or salicylyl-CoA
3
glycine
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reaction with benzoyl-CoA
5
glycine
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purified recombinant S156 haplotype, apparent value, ordered bi-bi (sequential) mechanism, at pH 8.0, temperature not specified in the publication
6.1
glycine
pH 8.0, temperature not specified in the publication
8
glycine
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reaction with salicyl-CoA
20
glycine
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purified recombinant S156 haplotype, apparent value, random bi-bi (sequential) mechanism, at pH 8.0, temperature not specified in the publication
21
glycine
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purified recombinant S156 haplotype, apparent value, ping-pong bi-bi (non-sequential) mechanism, at pH 8.0, temperature not specified in the publication
50
glycine
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reaction with butyryl-CoA
79
glycine
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reaction with butyryl-CoA
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4.2
benzoyl-CoA
pH 8.0, temperature not specified in the publication
3.2
glycine
pH 8.0, temperature not specified in the publication
0.57
glycine ethyl ester
pH 8.0, temperature not specified in the publication
1
Glycine methyl ester
pH 8.0, temperature not specified in the publication
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450
benzoyl-CoA
pH 8.0, temperature not specified in the publication
0.52
glycine
pH 8.0, temperature not specified in the publication
0.059
glycine ethyl ester
pH 8.0, temperature not specified in the publication
0.035
Glycine methyl ester
pH 8.0, temperature not specified in the publication
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55.2
benzoylalanine
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with variable Gly concentration
8.6
benzoylasparagine
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with variable Gly concentration
11.8
benzoylglutamic acid
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with variable Gly concentration
0.2
benzoylglycine
-
with variable Gly concentration
8.2
benzoylserine
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with variable Gly concentration
0.03 - 0.075
hippuric acid
0.03
hippuric acid
-
-
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58
glycolic acid
Mus musculus
pH 8.0, temperature not specified in the publication
0.021
oleoyl-CoA
Mus musculus
pH 8.0, temperature not specified in the publication
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additional information
for mutant E226Q, activity increases significantly when raising the pH above 8.0, while for wild-type, activity remains more or less stable up to pH 9.0
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UniProt
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UniProt
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UniProt
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isoform Glyat
UniProt
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enzyme activity is reduced by 66% in bile duct ligation animals
brenda
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enzyme activity is reduced by approximately 60% in hepatic mitochondria from cirrhotic rats
brenda
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brenda
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enzyme activity shows significant increase between the 1st and 7th day after common bile duct ligation
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brenda
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brenda
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brenda
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brenda
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brenda
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enzyme activity shows significant increase between the 1st and 7th day after common bile duct ligation
brenda
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GLYAT_BOVIN
295
0
33907
Swiss-Prot
other Location (Reliability: 5 )
GLYAT_HUMAN
296
0
33924
Swiss-Prot
other Location (Reliability: 5 )
GLYAT_MOUSE
296
0
34098
Swiss-Prot
other Location (Reliability: 4 )
GLYAT_PONAB
296
0
33855
Swiss-Prot
Mitochondrion (Reliability: 3 )
GLYAT_RAT
296
0
33899
Swiss-Prot
other Location (Reliability: 2 )
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27000
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x * 27000, SDS-PAGE
32400
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sucrose density gradient centrifugation
33000
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1 * 33000, SDS-PAGE
36000
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x * 36000, SDS-PAGE
34000
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gel filtration
34000
-
1 * 34000, SDS-PAGE
34000
x * 34000, calculated
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?
-
x * 36000, SDS-PAGE
monomer
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1 * 34000, SDS-PAGE
monomer
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1 * 33000, SDS-PAGE
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molecular model containing coenzyme A. The inactivity of the R199C variant could be due to the substitution of the highly conserved Arg199 and destabilisation of an alpha-loop-alpha motif which is important for substrate binding
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E226Q
about 3fold increase in Km value for lgycine
E229Q
single nucleotide polymorphism, inactive
F168L
single nucleotide polymorphism, decreased activity compared to wild-type
K16N
single nucleotide polymorphism, enzymic activities similar to wild-type
N156S
single nucleotide polymorphism, more active than wild-type
R131H
single nucleotide polymorphism, enzymic activities similar to wild-type
R199C
single nucleotide polymorphism, inactive
S17T
single nucleotide polymorphism, enzymic activities similar to wild-type
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-70°C, enzyme retains more than half of its activity after several months
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4°C, 3 weeks, enzyme retains about 80% of its initial activity
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nickel-affinity column chromatography
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expressed in Escherichia coli
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expression in Escherichia coli
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expression in Escherichia coli
expression in Escherichia coli
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isoform Glyat expression is suppressed in all hepatocellular carcinomas, but not in other liver diseases. Glyat repression in cancerous cells in the liver is controlled at the transcriptional level
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medicine
isoform Glyat expression is suppressed in all hepatocellular carcinomas, but not in other liver diseases. Glyat repression in cancerous cells in the liver is controlled at the transcriptional level
medicine
in a small cohort of South African Caucasian individuals, the two most prominent GLYAT haplotypes in all populations analysed, are S156 (70%) and T17S156 (20%). The S156C199 and S156H131 haplotypes, which have a negative effect on the enzyme activity of a recombinant human GLYAT, are detected at very low frequencies. An additional Q61L SNP occurring at a high frequency (12%) was detected
medicine
study to investigate 4-aminobenzoic acid as an alternative glycine conjugation probe. All of the participants were homozygous for increased enzyme activity, but excretion of product 4-amino-N-benzoylglycine varies significantly (16-56%, hippurate ratio)
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Nandi, D.L.; Lucas, S.V.; Webster, L.T.
Benzoyl-coenzyme A:glycine N-acyltransferase and phenylacetyl-coenzyme A:glycine N-acyltransferase from bovine liver mitochondria. Purification and characterization
J. Biol. Chem.
254
7230-7237
1979
Bos taurus
brenda
Webster, L.T.
Benzoyl-CoA: amino acid and phenylacetyl-CoA: amino acid N-acyltransferases
Methods Enzymol.
77
301-308
1981
Bos taurus
brenda
Van der Westhuizen, F.H.; Pretorius, P.J.; Erasmus, E.
The utilization of alanine, glutamic acid, and serine as amino acid substrates for glycine N-acyltransferase
J. Biochem. Mol. Toxicol.
14
102-109
2000
Bos taurus, Homo sapiens
brenda
Krahenbuhl, L.; Reichen, J.; Talos, C.; Krahenbuhl, S.
Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis
Hepatology
25
278-283
1997
Rattus norvegicus
brenda
Kelley, M.; Vessey, D.A.
The effects of ions on the conjugation of xenobiotics by the aralkyl-CoA and arylacetyl-CoA N-acyltransferases from bovine liver mitochondria
J. Biochem. Toxicol.
5
125-135
1990
Bos taurus
brenda
Kelley, M.; Vessey, D.A.
Isolation and characterization of mitochondrial acyl-CoA: glycine N-acyltransferases from kidney
J. Biochem. Toxicol.
8
63-69
1993
Bos taurus
brenda
Kelley, M.; Vessey, D.A.
Characterization of the acyl-CoA:amino acid N-acyltransferases from primate liver mitochondria
J. Biochem. Toxicol.
9
153-158
1994
Homo sapiens
brenda
Krahenbuhl, L.; Ledermann, M.; Lang, C.; Krahenbuhl, S.
Relationship between hepatic mitochondrial functions in vivo and in vitro in rats with carbon tetrachloride-induced liver cirrhosis
J. Hepatol.
33
216-223
2000
Rattus norvegicus
brenda
Kim, Y.J.; Kim, Y.H.
Benzoyltransferase and phenylacetyltransferase activities in cholestatic rat liver induced by common bile duct ligation
J. Biochem. Mol. Biol.
32
67-71
1999
Rattus norvegicus
-
brenda
Matsuo, M.; Terai, K.; Kameda, N.; Matsumoto, A.; Kurokawa, Y.; Funase, Y.; Nishikawa, K.; Sugaya, N.; Hiruta, N.; Kishimoto, T.
Designation of enzyme activity of glycine-N-acyltransferase family genes and depression of glycine-N-acyltransferase in human hepatocellular carcinoma
Biochem. Biophys. Res. Commun.
420
901-906
2012
Homo sapiens (Q6IB77)
brenda
Badenhorst, C.P.; Jooste, M.; van Dijk, A.A.
Enzymatic characterization and elucidation of the catalytic mechanism of a recombinant bovine glycine N-acyltransferase
Drug Metab. Dispos.
40
346-352
2012
Bos taurus (Q2KIR7)
brenda
Van der Sluis, R.; Badenhorst, C.; Van der Westhuizen, F.; Van Dijk, A.
Characterisation of the influence of genetic variations on the enzyme activity of a recombinant human glycine N-acyltransferase
Gene
515
447-453
2013
Homo sapiens (Q6IB77)
brenda
van der Sluis, R.; Badenhorst, C.P.; Erasmus, E.; van Dyk, E.; van der Westhuizen, F.H.; van Dijk, A.A.
Conservation of the coding regions of the glycine N-acyltransferase gene further suggests that glycine conjugation is an essential detoxification pathway
Gene
571
126-134
2015
Homo sapiens (Q6IB77)
brenda
Nortje, C.; van der Sluis, R.; van Dijk, A.A.; Erasmus, E.
The use of p-aminobenzoic acid as a probe substance for the targeted profiling of glycine conjugation
J. Biochem. Mol. Toxicol.
30
136-147
2015
Homo sapiens (Q6IB77)
brenda
Dempsey, D.R.; Bond, J.D.; Carpenter, A.M.; Rodriguez Ospina, S.; Merkler, D.J.
Expression, purification, and characterization of mouse glycine N-acyltransferase in Escherichia coli
Protein Expr. Purif.
97
23-28
2014
Mus musculus (Q91XE0)
brenda
van der Sluis, R.; Ungerer, V.; Nortje, C.; A van Dijk, A.; Erasmus, E.
New insights into the catalytic mechanism of human glycine N-acyltransferase
J. Biochem. Mol. Toxicol.
31
e21963
2017
Homo sapiens
brenda
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