Information on EC 2.3.1.71 - glycine N-benzoyltransferase

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The expected taxonomic range for this enzyme is: Eutheria

EC NUMBER
COMMENTARY
2.3.1.71
-
RECOMMENDED NAME
GeneOntology No.
glycine N-benzoyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzoyl-CoA + glycine = CoA + hippurate
show the reaction diagram
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
-
benzoyl-CoA + glycine = CoA + hippurate
show the reaction diagram
sequential two-substrate mechanism
-
benzoyl-CoA + glycine = CoA + hippurate
show the reaction diagram
residue Glu226 functions to deprotonate glycine, facilitating nucleophilic attack on the acyl-CoA substrate
Q2KIR7
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Phenylalanine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
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
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
aralkyl-CoA:glycine N-acyltransferase
-
-
-
-
benzoyl CoA-amino acid N-acyltransferase
-
-
-
-
benzoyl-CoA:glycine N-acyltransferase
-
-
-
-
benzoyltransferase, glycine
-
-
-
-
glycine N-acyltransferase
-
-
-
-
GNAT
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
71567-07-2
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoform Glyat
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-methylcrotonyl-CoA + glycine
CoA + N-3-methylcrotonylglycine
show the reaction diagram
-
-
-
-
?
3-methylcrotonyl-CoA + glycine
CoA + N-3-methylcrotonylglycine
show the reaction diagram
-
32% of the activity with benzoyl-CoA
-
-
?
acetyl-CoA + glycine
CoA + N-acetylglycine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + glycine
CoA + N-acetylglycine
show the reaction diagram
-
32% of the activity with benzoyl-CoA
-
-
?
benzoyl-CoA + alanine
CoA + N-benzoylalanine
show the reaction diagram
-
0.23% of the activity with Gly
-
?
benzoyl-CoA + alanine
CoA + N-benzoylalanine
show the reaction diagram
-
5% of the activity with Gly
-
-
?
benzoyl-CoA + glutaminic acid
CoA + N-benzoylglutamic acid
show the reaction diagram
-
-
-
-
-
benzoyl-CoA + glutaminic acid
CoA + N-benzoylglutamic acid
show the reaction diagram
-
0.06% of the activity with Gly
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
-
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
-
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
-
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
Q2KIR7
-
-
-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
show the reaction diagram
Q6IB77
best substrates are benzoyl-CoA as an acyl donor and glycine as acyl acceptor
-
-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
show the reaction diagram
-
-
-
-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
show the reaction diagram
-
weak activity
-
-
?
benzoyl-CoA + L-asparagine
CoA + N-benzoylasparagine
show the reaction diagram
-
1.88% of the activity with Gly
-
-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoyl-L-glutamine
show the reaction diagram
Q6IB77
24% of the rate with glycine and benzoyl-CoA
-
-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoylglutamine
show the reaction diagram
-
weak activity
-
-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoylglutamine
show the reaction diagram
-
0.52% of the activity with Gly
-
-
?
benzoyl-CoA + serine
CoA + N-benzoylserine
show the reaction diagram
-
0.88% of the activity with Gly
-
-
?
benzoyl-CoA + serine
CoA + N-benzoylserine
show the reaction diagram
-
0.03% of the activity with Gly
-
-
?
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
show the reaction diagram
-
9.5% of the activity with benzoyl-CoA
-
-
?
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
show the reaction diagram
-
3.9% of the activity with benzoyl-CoA
-
?
indoleacetyl-CoA + glycine
CoA + N-indoleacetylglycine
show the reaction diagram
-
-
-
-
?
isobutyryl-CoA + glycine
CoA + N-isobutyrylglycine
show the reaction diagram
-
-
-
-
?
isobutyryl-CoA + glycine
CoA + N-isobutyrylglycine
show the reaction diagram
-
25% of the activity with benzoyl-CoA
-
-
?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
show the reaction diagram
-
-
-
-
?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
show the reaction diagram
-
8.4% of the activity with benzoyl-CoA
-
-
?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
show the reaction diagram
-
9.1% of the activity with benzoyl-CoA
-
-
?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
show the reaction diagram
-
103% of the activity with benzoyl-CoA
-
-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
show the reaction diagram
-
-
-
-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
show the reaction diagram
-
19% of the activity with benzoyl-CoA
-
-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
show the reaction diagram
-
223% of the activity with benzoyl-CoA
-
-
?
n-butyryl-CoA + glycine
CoA + N-butyrylglycine
show the reaction diagram
-
28% of the activity with benzoyl-CoA
-
-
?
naphthylacetyl-CoA + glycine
CoA + N-naphthylacetylglycine
show the reaction diagram
-
-
-
-
?
phenylacetyl-CoA + glycine
CoA + N-phenylacetylglycine
show the reaction diagram
-
-
-
-
?
phenylacetyl-CoA + glycine
CoA + N-phenylacetylglycine
show the reaction diagram
Q6IB77
22% of the rate with glycine and benzoyl-CoA
-
-
?
phenylacetyl-CoA + L-glutamine
CoA + N-phenylacetyl-L-glutamine
show the reaction diagram
Q6IB77
20% of the rate with glycine and benzoyl-CoA
-
-
?
propionyl-CoA + glycine
CoA + N-propionylglycine
show the reaction diagram
-
-
-
-
?
propionyl-CoA + glycine
CoA + N-propionylglycine
show the reaction diagram
-
53% of the activity with benzoyl-CoA
-
-
?
salicyl-CoA + glycine
CoA + N-salicylglycine
show the reaction diagram
-
-
-
-
?
salicyl-CoA + glycine
CoA + N-salicylglycine
show the reaction diagram
-
35% of the activity with benzoyl-CoA
-
-
?
salicyl-CoA + glycine
CoA + N-salicylglycine
show the reaction diagram
-
22% of the activity with benzoyl-CoA
-
-
?
salicyl-CoA + glycine
CoA + N-salicylglycine
show the reaction diagram
-
15% of the activity with benzoyl-CoA
-
-
?
tiglyl-CoA + glycine
CoA + N-tiglylglycine
show the reaction diagram
-
-
-
-
?
tiglyl-CoA + glycine
CoA + N-tiglylglycine
show the reaction diagram
-
115% of the activity with benzoyl-CoA
-
-
?
methylmalonyl-CoA + glycine
CoA + N-methylmalonylglycine
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
enzyme synthesis is induced in response to cholestasis
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
enzyme synthesis is induced in response to cholestasis
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3'-Dephospho-CoA
-
-
benzoylalanine
-
-
benzoylasparagine
-
-
benzoylglutamic acid
-
-
benzoylglycine
-
-
benzoylserine
-
-
CoA
-
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
hippuric acid
-
competitive with respect to benzoyl-CoA
hippuric acid
-
-
indolacetyl-CoA
-
-
K+
-
200 mM KCl, 44% inhibition
K+
-
K+ is a competitive inhibitor for benzoyl-coenzyme A, not a competitive inhibitor for salicylyl-CoA, K+ increases Km-value for glycine 10fold
K+
-
100 mM, 50% inhibition
Li+
-
110 mM
Mg2+
-
100 mM MgCl2, 90% inhibition
Na+
-
110 mM
Ni2+
-
10 mM NiCl2, 98% inhibition
Ni2+
-
-
p-hydroxymercuribenzoate
-
1 mM, 24C, 90% inhibition after 40 min
phenylacetyl-CoA
-
-
potassium phosphate
-
-
Rb+
-
110 mM
Zn2+
-
1 mM ZnCl2, 13% inhibition
Zn2+
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
997
Ala
-
-
1573
Ala
-
-
129
Asn
-
-
0.016
benzoyl-CoA
Q2KIR7
recombinant wild-type, pH 8.0, 30C; wild-type, pH 8.0, 30C
0.018
benzoyl-CoA
Q2KIR7
mutant E226Q, pH 8.0, 30C
13
benzoyl-CoA
-
reaction with Gly
13
benzoyl-CoA
-
-
15.2
benzoyl-CoA
-
reaction with Ala
15.2
benzoyl-CoA
-
-
20
benzoyl-CoA
-
-
41
benzoyl-CoA
-
reaction with Ala
45
benzoyl-CoA
-
reaction with L-Asn or L-Gln
105
benzoyl-CoA
-
reaction with Gln
157
benzoyl-CoA
-
reaction with Asn
160
benzoyl-CoA
-
reaction with Gly
998
benzoyl-CoA
-
reaction with Glu
130
Butyryl-CoA
-
-
353
Gln
-
-
1148
Glu
-
-
6
Gly
-
reaction with benzoyl-CoA
6.2
Gly
-
-
6.4
Gly
-
-
0.0016
glycine
Q2KIR7
wild-type, pH 8.0, 30C
0.002
glycine
Q2KIR7
recombinant wild-type, pH 8.0, 30C
0.007
glycine
Q2KIR7
mutant E226Q, pH 8.0, 30C
2
glycine
-
reaction with benzoyl-CoA or salicylyl-CoA
3
glycine
-
reaction with benzoyl-CoA
8
glycine
-
reaction with salicyl-CoA
50
glycine
-
reaction with butyryl-CoA
79
glycine
-
reaction with butyryl-CoA
170
L-asparagine
-
-
130
L-glutamine
-
-
360
methylmalonyl-CoA
-
-
7.6
salicyl-CoA
-
reaction with salicylyl-CoA
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
55.2
benzoylalanine
-
with variable Gly concentration
8.6
benzoylasparagine
-
with variable Gly concentration
11.8
benzoylglutamic acid
-
with variable Gly concentration
0.2
benzoylglycine
-
with variable Gly concentration
8.2
benzoylserine
-
with variable Gly concentration
0.03
hippuric acid
-
-
0.075
hippuric acid
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5 - 8.5
Q2KIR7
wild-type
8.4 - 8.6
-
-
additional information
Q2KIR7
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
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
enzyme activity is reduced by 66% in bile duct ligation animals
Manually annotated by BRENDA team
-
enzyme activity is reduced by approximately 60% in hepatic mitochondria from cirrhotic rats
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
enzyme activity shows significant increase between the 1st and 7th day after common bile duct ligation
-
Manually annotated by BRENDA team
-
enzyme activity shows significant increase between the 1st and 7th day after common bile duct ligation
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30500
-
gel filtration
487441
32400
-
sucrose density gradient centrifugation
486265
33500
-
gel filtration
487440
33800
-
gel filtration
486265
34000
-
gel filtration
487438
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 27000, SDS-PAGE
?
-
x * 36000, SDS-PAGE
monomer
-
1 * 34000, SDS-PAGE
monomer
-
1 * 33000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, enzyme retains more than half of its activity after several months
-
4C, 3 weeks, enzyme retains about 80% of its initial activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Q2KIR7
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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
Q6IB77
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E226Q
Q2KIR7
about 3fold increase in Km value for lgycine
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
Q6IB77
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