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Enzyme Nomenclature
Information on EC 2.3.1.144 - anthranilate N-benzoyltransferase
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The expected taxonomic range for this enzyme is: Dianthus caryophyllus
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EC NUMBER 
COMMENTARY 
2.3.1.144
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RECOMMENDED NAME
GeneOntology No.
anthranilate N-benzoyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzoyl-CoA + anthranilate = CoA + N-benzoylanthranilate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
125498-59-1
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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
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,3-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-3-hydroxyanthranilate
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-
-
?
2,3-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-anthranilate
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-
-
?
2,4-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,4-dimethoxycinnamoyl)-anthranilate
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-
-
?
2,5-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-3-hydroxyanthranilate
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-
-
?
2,5-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-anthranilate
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-
-
?
2-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(2-coumaroyl)-3-hydroxyanthranilate
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-
-
?
2-coumaroyl-CoA + anthranilate
CoA + N-(2-coumaroyl)anthranilate
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-
-
?
3,4,5-trimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-3-hydroxyanthranilate
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-
-
?
3,4,5-trimethoxycinnamoyl-CoA + anthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-anthranilate
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-
-
?
3,4-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4-dimethoxycinnamoyl)-3-hydroxyanthranilate
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-
-
?
3-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-coumaroyl)-3-hydroxyanthranilate
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-
-
?
3-coumaroyl-CoA + anthranilate
CoA + N-(3-hydroxycinnamoyl)-anthranilate
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-
-
?
3-hydroxy-4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-hydroxy-4-methoxycinnamoyl)-anthranilate
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-
-
?
3-methoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-methoxycinnamoyl)-3-hydroxyanthranilate
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-
-
?
3-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-methoxycinnamoyl)-anthranilate
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-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(4-coumaroyl)-3-hydroxyanthranilate
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-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-(4-coumaroyl)-anthranilate
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product detection by mass spectrometry
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?
4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(4-methoxycinnamoyl)-anthranilate
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-
-
?
benzoyl-CoA + 3-hydroxyanthranilate
CoA + N-benzoyl-3-hydroxyanthranilate
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20% of activity with anthranilate
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?
benzoyl-CoA + 4-hydroxyanthranilate
CoA + N-benzoyl-4-hydroxyanthranilate
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10% of activity with anthranilate
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?
caffeoyl-CoA + 3-hydroxyanthranilate
CoA + N-caffeoyl-3-hydroxyanthranilate
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-
-
?
caffeoyl-CoA + anthranilate
CoA + N-(3,4-dihydroxycinnamoyl)-anthranilate
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-
-
?
cinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-cinnamoyl-3-hydroxyanthranilate
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-
-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinammoylanthranilate
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140% of activity with benzoyl-CoA
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-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinnamoylanthranilate
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-
-
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
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product detection by mass spectrometry
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?
feruloyl-CoA + 3-hydroxyanthranilate
CoA + N-feruloyl-3-hydroxyanthranilate
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-
-
?
feruloyl-CoA + anthranilate
CoA + N-feruloylanthranilate
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-
-
?
salicyl-CoA + anthranilate
CoA + N-salicylanthranilate
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60% of activity with benzoyl-CoA
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-
?
sinapoyl-CoA + 3-hydroxyanthranilate
CoA + N-sinapoyl-3-hydroxyanthranilate
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-
-
?
sinapoyl-CoA + anthranilate
CoA + N-sinapoylanthranilate
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-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
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-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
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127% of activity with benzoyl-CoA
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?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
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cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
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benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
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cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
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?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
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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
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?
additional information
?
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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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additional information
?
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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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additional information
?
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by exploiting the substrate flexibility of both 4-coumaroyl:CoA ligase 4CL5 from Arabidopsis thaliana and HCBT, rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast can be achieved. The enzyme offers flexibility for a wide range of acyl-CoA donors, its affinity towards acceptors seems limited to anthranilates
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
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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
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?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
O24645
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product detection by mass spectrometry
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?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8 - 7
additional information
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true pH-optimum may be closer to the amino-pK of anthranilate at 4.95
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6
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crude extract, 4�C, almost all activity irreversibly lost within less than 2 h
485081
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, Q-Sepharose, Blue Sepharose, Sephacryl S200, Mono Q
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of HCBT in Saccharomyces cerevisiae, coexpression with 4-coumarate/CoA ligase from Arabidopsis thaliana using yeast shuttle vector pDRf1-GW-PHXT7
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
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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
additional information
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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
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coexpression of HCBT and 4-coumarate:CoA 4CL1 ligase from Nicotiana tabacum in the Escherichia coli anthranilate-accumulating strain W3110 trpD9923 allows the production of Avn D [N-(4'-hydroxycinnamoyl)-anthranilic acid] and Avn F [N-(3',4'-dihydroxycinnamoyl)-anthranilic acid] upon feeding with p-coumarate and caffeate, respectively. Additional expression of a tyrosine ammonia-lyase from Rhodotorula glutinis (TAL) leads to the conversion of endogenous tyrosine into p-coumarate and results in the production of Avn D [N-(4'-hydroxycinnamoyl)-anthranilic acid] from glucose. A 135fold improvement in Avn D titer is achieved by boosting tyrosine production. Expression of either the p-coumarate 3-hydroxylase Sam5 from Saccharothrix espanensis or the hydroxylase complex HpaBC from Escherichia coli results in the endogenous production of caffeate and biosynthesis of Avn F [N-(3',4'-dihydroxycinnamoyl)-anthranilic acid]
synthesis
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by exploiting the substrate flexibility of both 4-coumaroyl:CoA ligase 4CL5 from Arabidopsis thaliana and HCBT, rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast can be achieved upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates
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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.144)
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