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Information on EC 2.3.1.144 - anthranilate N-benzoyltransferase
for references in articles please use BRENDA:EC2.3.1.144
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.144 anthranilate N-benzoyltransferase
IUBMB Comments
Cinnamoyl-CoA, 4-coumaroyl-CoA and salicyloyl-CoA can act as donors, but more slowly. Involved in the biosynthesis of phytoalexins.
The enzyme appears in viruses and cellular organisms
- 2.3.1.144
- gold
-
alloy
- dianthus
-
dental
- caryophyllus
- carnation
-
healthcare
-
phytoalexins
-
hardening
- 4-coumaroyl-coa
-
hardness
- cinnamates
- synthesis
showSynonyms
hydroxycinnamoyl/benzoyl-coa/anthranilate n-hydroxycinnamoyl/benzoyltransferase, anthranilate n-benzoyltransferase, benzoyl-coa:anthranilate n-benzoyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase
-
benzoyltransferase, anthranilate N-
-
-
-
-
hydroxycinnamoyl/benzoyl-CoA/anthranilate
N-hydroxycinnamoyl/benzoyltransferase
-
hydroxycinnamoyl/benzoyl-CoA/anthranilate N-hydroxycinnamoyl/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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PATHWAY SOURCE
PATHWAYS
MetaCyc
benzoylanthranilate biosynthesis
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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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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
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
Substrates: -
Products: -
Products: -
?
2,3-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
2,4-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,4-dimethoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
2,5-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
2,5-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
2-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(2-coumaroyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
2-coumaroyl-CoA + anthranilate
CoA + N-(2-coumaroyl)anthranilate
Substrates: -
Products: -
Products: -
?
3,4,5-trimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
3,4,5-trimethoxycinnamoyl-CoA + anthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
3,4-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4-dimethoxycinnamoyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
3-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-coumaroyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
3-coumaroyl-CoA + anthranilate
CoA + N-(3-hydroxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
3-hydroxy-4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-hydroxy-4-methoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
3-methoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-methoxycinnamoyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
3-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-methoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(4-coumaroyl)-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
4-coumaroyl-CoA + anthranilate
CoA + N-(4-coumaroyl)-anthranilate
Substrates: -
Products: product detection by mass spectrometry
Products: product detection by mass spectrometry
?
4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(4-methoxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
benzoyl-CoA + 3-hydroxyanthranilate
CoA + N-benzoyl-3-hydroxyanthranilate
-
Substrates: 20% of activity with anthranilate
Products: -
Products: -
?
benzoyl-CoA + 4-hydroxyanthranilate
CoA + N-benzoyl-4-hydroxyanthranilate
-
Substrates: 10% of activity with anthranilate
Products: -
Products: -
?
caffeoyl-CoA + 3-hydroxyanthranilate
CoA + N-caffeoyl-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
caffeoyl-CoA + anthranilate
CoA + N-(3,4-dihydroxycinnamoyl)-anthranilate
Substrates: -
Products: -
Products: -
?
cinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-cinnamoyl-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
Substrates: -
Products: product detection by mass spectrometry
Products: product detection by mass spectrometry
?
feruloyl-CoA + 3-hydroxyanthranilate
CoA + N-feruloyl-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
feruloyl-CoA + anthranilate
CoA + N-feruloylanthranilate
Substrates: -
Products: -
Products: -
?
salicyl-CoA + anthranilate
CoA + N-salicylanthranilate
-
Substrates: 60% of activity with benzoyl-CoA
Products: -
Products: -
?
sinapoyl-CoA + 3-hydroxyanthranilate
CoA + N-sinapoyl-3-hydroxyanthranilate
Substrates: -
Products: -
Products: -
?
sinapoyl-CoA + anthranilate
CoA + N-sinapoylanthranilate
Substrates: -
Products: -
Products: -
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
-
Substrates: 127% of activity with benzoyl-CoA
Products: -
Products: -
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
Substrates: -
Products: -
Products: -
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
Substrates: cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
Products: -
Products: -
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
Substrates: 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
Products: -
Products: -
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
Substrates: -
Products: -
Products: -
?
cinnamoyl-CoA + anthranilate
CoA + N-cinnamoylanthranilate
-
Substrates: 140% of activity with benzoyl-CoA
Products: -
Products: -
?
cinnamoyl-CoA + anthranilate
CoA + N-cinnamoylanthranilate
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
Substrates: 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
Products: -
Products: -
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
Substrates: -
Products: product detection by mass spectrometry
Products: product detection by mass spectrometry
?
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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
-
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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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
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). HCBT2_DIACA
446
0
50147
Swiss-Prot
other Location (Reliability: 3)
A0A0J8B762_BETVV
446
0
50445
TrEMBL
Secretory Pathway (Reliability: 4)
A0A803MV07_CHEQI
362
0
40407
TrEMBL
other Location (Reliability: 3)
A0A9Q1JM32_9CARY
442
0
48920
TrEMBL
Secretory Pathway (Reliability: 4)
A0A9Q1KYN9_9CARY
448
0
50294
TrEMBL
Secretory Pathway (Reliability: 1)
A0A9Q1Q6D3_9CARY
444
0
49136
TrEMBL
other Location (Reliability: 4)
A0A9R0IMU6_SPIOL
465
0
52930
TrEMBL
other Location (Reliability: 2)
A0AAD3SNH5_NEPGR
288
0
32018
TrEMBL
Chloroplast (Reliability: 3)
A0AAW1H5F8_SAPOF
437
0
48134
TrEMBL
other Location (Reliability: 4)
A0AAW1H0K6_SAPOF
445
0
49493
TrEMBL
other Location (Reliability: 5)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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
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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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6
-
crude extract, 4°C, almost all activity irreversibly lost within less than 2 h
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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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
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
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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Reinhard, K.; Matern, U.
The biosynthesis of phytoalexins in Dianthus caryophyllus L. cell cultures: induction of benzoyl-CoA:anthranilate N-benzoyltransferase activity
Arch. Biochem. Biophys.
275
295-301
1989
Dianthus caryophyllus
brenda
Yang, Q.; Reinhard, K.; Schiltz, E.; Matern, U.
Characterization and heterologous expression of hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase from elicited cell cultures of carnation, Dianthus caryophyllus L
Plant Mol. Biol.
35
777-789
1997
Dianthus caryophyllus
brenda
Yang, Q.; Grimmig, B.; Matern, U.
Anthranilate N-hydroxycinnamoyl/benzoyltransferase gene from carnation: rapid elicitation of transcription and promoter analysis
Plant Mol. Biol.
38
1201-1214
1998
Dianthus caryophyllus
brenda
Eudes, A.; Baidoo, E.E.; Yang, F.; Burd, H.; Hadi, M.Z.; Collins, F.W.; Keasling, J.D.; Loque, D.
Production of tranilast [N-(3,4-dimethoxycinnamoyl)-anthranilic acid] and its analogs in yeast Saccharomyces cerevisiae
Appl. Microbiol. Biotechnol.
89
989-1000
2011
Dianthus caryophyllus (O24645), Dianthus caryophyllus
brenda
Eudes, A.; Juminaga, D.; Baidoo, E.E.; Collins, F.W.; Keasling, J.D.; Loque, D.
Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli
Microb. Cell Fact.
12
62
2013
Dianthus caryophyllus (O24645)
brenda
Eudes, A.; Teixeira Benites, V.; Wang, G.; Baidoo, E.E.; Lee, T.S.; Keasling, J.D.; Loque, D.
Precursor-directed combinatorial biosynthesis of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in Saccharomyces cerevisiae
PLoS ONE
10
e0138972
2015
Dianthus caryophyllus (O24645)
brenda
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