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 ACCESSION NO.
LITERATURE
benzoyl-CoA + anthranilate = CoA + N-benzoylanthranilate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
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 ACCESSION NO.
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
SEQUENCE CODE
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 ACCESSION NO.
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
-
-
?
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
-
-
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 ACCESSION NO.
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]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.02
-
anthranilate
-
-
0.033
-
anthranilate
-
-
0.009
-
benzoyl-CoA
-
-
0.05
-
benzoyl-CoA
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.00000948
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
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
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
44000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
-
1 * 53000, SDS-PAGE
pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6
-
-
crude extract, 4°C, almost all activity irreversibly lost within less than 2 h
7
-
-
very labile at pH below
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
40
-
-
crude extract, 5 min, pH 7.5, significant loss of activity
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
ammonium sulfate, Q-Sepharose, Blue Sepharose, Sephacryl S200, Mono Q
-
ammonium sulfate, Q-Sepharose, partially purified
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
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