Information on EC 2.3.1.144 - anthranilate N-benzoyltransferase

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The expected taxonomic range for this enzyme is: Dianthus caryophyllus

EC NUMBER
COMMENTARY
2.3.1.144
-
RECOMMENDED NAME
GeneOntology No.
anthranilate N-benzoyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzoyl-CoA + anthranilate = CoA + N-benzoylanthranilate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
benzoylanthranilate biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
benzoyl-CoA:anthranilate N-benzoyltransferase
Cinnamoyl-CoA, 4-coumaroyl-CoA and salicyloyl-CoA can act as donors, but more slowly. Involved in the biosynthesis of phytoalexins.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
anthranilate N-hydroxycinammoyl/benzoyltransferase
-
-
benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase
O24645
-
benzoyltransferase, anthranilate N-
-
-
-
-
hydroxycinnamoyl/
O24645
-
CAS REGISTRY NUMBER
COMMENTARY
125498-59-1
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
enzyme is induced by addition of crude elicitor from the cell walls of Phythophthora megasperma f. sp. glycinea or by commercial yeast extract
-
-
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
2,3-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
2,3-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
2,4-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,4-dimethoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
2,5-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
2,5-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
2-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(2-coumaroyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
2-coumaroyl-CoA + anthranilate
CoA + N-(2-coumaroyl)anthranilate
show the reaction diagram
O24645
-
-
-
?
3,4,5-trimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
3,4,5-trimethoxycinnamoyl-CoA + anthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
3,4-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4-dimethoxycinnamoyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
3-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-coumaroyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
3-coumaroyl-CoA + anthranilate
CoA + N-(3-hydroxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
3-hydroxy-4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-hydroxy-4-methoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
3-methoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-methoxycinnamoyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
3-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-methoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(4-coumaroyl)-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
show the reaction diagram
-
127% of activity with benzoyl-CoA
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-
?
4-coumaroyl-CoA + anthranilate
CoA + N-(4-coumaroyl)-anthranilate
show the reaction diagram
O24645
-
product detection by mass spectrometry
-
?
4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(4-methoxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
benzoyl-CoA + 3-hydroxyanthranilate
CoA + N-benzoyl-3-hydroxyanthranilate
show the reaction diagram
-
20% of activity with anthranilate
-
?
benzoyl-CoA + 4-hydroxyanthranilate
CoA + N-benzoyl-4-hydroxyanthranilate
show the reaction diagram
-
10% of activity with anthranilate
-
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
show the reaction diagram
-
cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
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-
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
show the reaction diagram
-
cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors, cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors with 73%, 70% and 65% efficiency respectively, enzyme is involved in the biosynthesis of phytoalexins, 4-hydroxyanthranilate is the most probable substrate in vivo
-
?
caffeoyl-CoA + 3-hydroxyanthranilate
CoA + N-caffeoyl-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
caffeoyl-CoA + anthranilate
CoA + N-(3,4-dihydroxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
-
-
?
cinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-cinnamoyl-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinammoylanthranilate
show the reaction diagram
-
140% of activity with benzoyl-CoA
-
-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinnamoylanthranilate
show the reaction diagram
O24645
-
-
-
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
product detection by mass spectrometry
-
?
feruloyl-CoA + 3-hydroxyanthranilate
CoA + N-feruloyl-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
salicyl-CoA + anthranilate
CoA + N-salicylanthranilate
show the reaction diagram
-
60% of activity with benzoyl-CoA
-
-
?
sinapoyl-CoA + 3-hydroxyanthranilate
CoA + N-sinapoyl-3-hydroxyanthranilate
show the reaction diagram
O24645
-
-
-
?
sinapoyl-CoA + anthranilate
CoA + N-sinapoylanthranilate
show the reaction diagram
O24645
-
-
-
?
feruloyl-CoA + anthranilate
CoA + N-feruloylanthranilate
show the reaction diagram
O24645
-
-
-
?
additional information
?
-
O24645
hydroxycinnamoyl/benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase, HCBT, has affinity for anthranilate and 4-coumaroyl-CoA and is capable of producing N-(4-hydroxycinnamoyl)-anthranilate in vitro
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
show the reaction diagram
-
cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors with 73%, 70% and 65% efficiency respectively, enzyme is involved in the biosynthesis of phytoalexins, 4-hydroxyanthranilate is the most probable substrate in vivo
-
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
show the reaction diagram
O24645
-
product detection by mass spectrometry
-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.02
anthranilate
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-
0.033
anthranilate
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-
0.009
benzoyl-CoA
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-
0.05
benzoyl-CoA
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.00000948
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-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8 - 7
-
crude extract, assay at pH 7.0
6.8 - 7
-
activity is completely lost if the pH drops below pH 6.5
additional information
-
true pH-optimum may be closer to the amino-pK of anthranilate at 4.95
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
44000
-
gel filtration
486330
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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1 * 53000, SDS-PAGE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6
-
crude extract, 4°C, almost all activity irreversibly lost within less than 2 h
485081
7
-
very labile at pH below
485081
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
40
-
crude extract, 5 min, pH 7.5, significant loss of activity
485081
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, Q-Sepharose, Blue Sepharose, Sephacryl S200, Mono Q
-
ammonium sulfate, Q-Sepharose, partially purified
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of 2 cDNAs
-
expression in Escherichia coli
-
expression of HCBT in Saccharomyces cerevisiae, coexpression with 4-coumarate/CoA ligase from Arabidopsis thaliana using yeast shuttle vector pDRf1-GW-PHXT7
O24645
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
O24645
for production of tranilast, i.e. N-(3,4-dimethoxycinnamoyl)-anthranilate, and several of its analogues, a yeast strain is engineered to coexpress a 4-coumarate/CoA ligase, EC 6.2.1.12, from Arabidopsis thaliana and the hydroxycinnamoyl/benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase from Dianthus caryophyllus. Production of tranilast and 26 different cinnamoyl anthranilate molecules within a few hours after exogenous supply of various combinations of cinnamic acids and anthranilate derivatives, method optimization, overview