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Information on EC 2.3.1.144 - anthranilate N-benzoyltransferase
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2.3.1.144 anthranilate N-benzoyltransferaseIUBMB Comments
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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Word Map
- 2.3.1.144
- gold
-
alloy
- dianthus
-
dental
- caryophyllus
- carnation
-
healthcare
-
phytoalexins
-
hardening
- 4-coumaroyl-coa
-
hardness
- cinnamates
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
anthranilate N-hydroxycinammoyl/benzoyltransferase, benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase, benzoyltransferase, anthranilate N-, HCBT, hydroxycinnamoyl/benzoyl-CoA/anthranilate
N-hydroxycinnamoyl/benzoyltransferase, hydroxycinnamoyl/benzoyl-CoA/anthranilate N-hydroxycinnamoyl/benzoyltransferase, 
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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
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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
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
-
-
-
?
2,3-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,3-dimethoxycinnamoyl)-anthranilate
-
-
-
?
2,4-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,4-dimethoxycinnamoyl)-anthranilate
-
-
-
?
2,5-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-3-hydroxyanthranilate
-
-
-
?
2,5-dimethoxycinnamoyl-CoA + anthranilate
CoA + N-(2,5-dimethoxycinnamoyl)-anthranilate
-
-
-
?
2-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(2-coumaroyl)-3-hydroxyanthranilate
-
-
-
?
2-coumaroyl-CoA + anthranilate
CoA + N-(2-coumaroyl)anthranilate
-
-
-
?
3,4,5-trimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-3-hydroxyanthranilate
-
-
-
?
3,4,5-trimethoxycinnamoyl-CoA + anthranilate
CoA + N-(3,4,5-trimethoxycinnamoyl)-anthranilate
-
-
-
?
3,4-dimethoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3,4-dimethoxycinnamoyl)-3-hydroxyanthranilate
-
-
-
?
3-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-coumaroyl)-3-hydroxyanthranilate
-
-
-
?
3-coumaroyl-CoA + anthranilate
CoA + N-(3-hydroxycinnamoyl)-anthranilate
-
-
-
?
3-hydroxy-4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-hydroxy-4-methoxycinnamoyl)-anthranilate
-
-
-
?
3-methoxycinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-(3-methoxycinnamoyl)-3-hydroxyanthranilate
-
-
-
?
3-methoxycinnamoyl-CoA + anthranilate
CoA + N-(3-methoxycinnamoyl)-anthranilate
-
-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + N-(4-coumaroyl)-3-hydroxyanthranilate
-
-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-(4-coumaroyl)-anthranilate
-
product detection by mass spectrometry
-
?
4-methoxycinnamoyl-CoA + anthranilate
CoA + N-(4-methoxycinnamoyl)-anthranilate
-
-
-
?
benzoyl-CoA + 3-hydroxyanthranilate
CoA + N-benzoyl-3-hydroxyanthranilate
-
20% of activity with anthranilate
-
?
benzoyl-CoA + 4-hydroxyanthranilate
CoA + N-benzoyl-4-hydroxyanthranilate
-
10% of activity with anthranilate
-
?
caffeoyl-CoA + 3-hydroxyanthranilate
CoA + N-caffeoyl-3-hydroxyanthranilate
-
-
-
?
caffeoyl-CoA + anthranilate
CoA + N-(3,4-dihydroxycinnamoyl)-anthranilate
-
-
-
?
cinnamoyl-CoA + 3-hydroxyanthranilate
CoA + N-cinnamoyl-3-hydroxyanthranilate
-
-
-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinammoylanthranilate
-
140% of activity with benzoyl-CoA
-
-
?
cinnamoyl-CoA + anthranilate
CoA + N-cinnamoylanthranilate
-
-
-
?
coumaroyl-CoA + anthranilate
CoA + N-(4-hydroxycinnamoyl)-anthranilate
-
product detection by mass spectrometry
-
?
feruloyl-CoA + 3-hydroxyanthranilate
CoA + N-feruloyl-3-hydroxyanthranilate
-
-
-
?
feruloyl-CoA + anthranilate
CoA + N-feruloylanthranilate
-
-
-
?
salicyl-CoA + anthranilate
CoA + N-salicylanthranilate
-
60% of activity with benzoyl-CoA
-
-
?
sinapoyl-CoA + 3-hydroxyanthranilate
CoA + N-sinapoyl-3-hydroxyanthranilate
-
-
-
?
sinapoyl-CoA + anthranilate
CoA + N-sinapoylanthranilate
-
-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
-
127% of activity with benzoyl-CoA
-
-
?
4-coumaroyl-CoA + anthranilate
CoA + N-4-(coumaroyl)anthranilate
-
-
-
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
-
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
cinnamoyl-CoA, salicyl-CoA and 4-coumaroyl-CoA can act as donors
-
?
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
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
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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 SUBSTRATE
NATURAL 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
benzoyl-CoA + anthranilate
CoA + N-benzoylanthranilate
-
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
-
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
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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). HCBT3_DIACA
445
0
50149
Swiss-Prot
other Location (Reliability: 2)
HCBT1_DIACA
445
0
50038
Swiss-Prot
other Location (Reliability: 2)
HCBT2_DIACA
446
0
50147
Swiss-Prot
other Location (Reliability: 2)
B9SB68_RICCO
423
0
46862
TrEMBL
other Location (Reliability: 5)
A0A0B2PW86_GLYSO
447
0
50237
TrEMBL
other Location (Reliability: 4)
B9T457_RICCO
440
0
49987
TrEMBL
other Location (Reliability: 2)
B9S503_RICCO
439
0
49402
TrEMBL
other Location (Reliability: 2)
A0A0B2RDA1_GLYSO
448
0
50593
TrEMBL
other Location (Reliability: 2)
A0A0B2RPK5_GLYSO
278
0
31597
TrEMBL
other Location (Reliability: 3)
B9RNX7_RICCO
463
0
51097
TrEMBL
other Location (Reliability: 2)
A0A0B2RT58_GLYSO
409
0
46451
TrEMBL
other Location (Reliability: 3)
A0A7C9A0D9_OPUST
112
0
12435
TrEMBL
other Location (Reliability: 4)
B9STU3_RICCO
404
0
45504
TrEMBL
other Location (Reliability: 2)
B9RIV2_RICCO
451
0
50176
TrEMBL
other Location (Reliability: 1)
B9STR5_RICCO
393
0
43839
TrEMBL
other Location (Reliability: 5)
A0A7C9F0F7_OPUST
99
0
11105
TrEMBL
other Location (Reliability: 4)
B9RGN0_RICCO
431
0
47364
TrEMBL
other Location (Reliability: 4)
B9S035_RICCO
462
0
51287
TrEMBL
other Location (Reliability: 2)
B9RAB0_RICCO
432
0
47749
TrEMBL
other Location (Reliability: 2)
B9T4T6_RICCO
437
0
48548
TrEMBL
other Location (Reliability: 5)
A0A0B2PYA4_GLYSO
232
0
25963
TrEMBL
other Location (Reliability: 2)
A0A0B2R2K3_GLYSO
369
0
41178
TrEMBL
Mitochondrion (Reliability: 4)
B9T456_RICCO
446
0
50405
TrEMBL
other Location (Reliability: 3)
B9T1C5_RICCO
455
0
50672
TrEMBL
other Location (Reliability: 2)
B9SN57_RICCO
280
0
31278
TrEMBL
other Location (Reliability: 2)
B9STU4_RICCO
425
0
47356
TrEMBL
other Location (Reliability: 2)
A0A0B2P4W8_GLYSO
466
0
52841
TrEMBL
other Location (Reliability: 3)
B9SLJ1_RICCO
477
0
53045
TrEMBL
Chloroplast (Reliability: 5)
B9SZD6_RICCO
468
0
52169
TrEMBL
other Location (Reliability: 4)
A0A0B2QRC6_GLYSO
328
0
36830
TrEMBL
other Location (Reliability: 3)
A0A0B2P9M0_GLYSO
462
0
52636
TrEMBL
Mitochondrion (Reliability: 4)
B9S6C4_RICCO
449
0
49922
TrEMBL
other Location (Reliability: 2)
B9RH39_RICCO
433
0
48267
TrEMBL
other Location (Reliability: 2)
A0A0B2QRC7_GLYSO
239
0
26689
TrEMBL
other Location (Reliability: 3)
A0A0B2Q2K7_GLYSO
658
0
73813
TrEMBL
Mitochondrion (Reliability: 3)
B9RM18_RICCO
450
0
50390
TrEMBL
other Location (Reliability: 2)
A0A7C8ZUS2_OPUST
118
0
13280
TrEMBL
other Location (Reliability: 3)
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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
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
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
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]
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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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