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Information on EC 6.2.1.12 - 4-coumarate-CoA ligase and Organism(s) Nicotiana tabacum and UniProt Accession O24146
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6.2.1.12 4-coumarate-CoA ligaseSpecify your search results
Word Map
- 6.2.1.12
-
phenylpropanoids
- lignin
- flavonoid
-
ammonia-lyase
- chalcone
-
ferulic
-
4-hydroxylase
-
p-coumaric
- xylem
-
caffeic
- parsley
- populus
- cinnamate-4-hydroxylase
-
sinapic
-
cinnamyl
- monolignols
- crispum
- stilbene
-
lignification
-
petroselinum
- caffeate
- trans-cinnamate
- dihydroflavonol
-
4.3.1.5
- taeda
-
4-reductase
-
cinnamoylated
-
elicitor-treated
- glycinea
-
3-o-methyltransferase
-
3\'-hydroxylase
- cinnamoyl-coa
-
guaiacyl
-
hydroxycinnamoyl-coas
- megasperma
-
syringyl
- ccoaomt
-
adenylate-forming
- biotechnology
- synthesis
- drug development
The taxonomic range for the selected organisms is: Nicotiana tabacum
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
4-coumarate:coa ligase, 4-coumarate:coenzyme a ligase, 4-coumarate-coa ligase, 4-coumarate coa ligase, 4-coumarate coenzyme a ligase, at4cl1, 4-coumaroyl-coa ligase, os4cl, pl4cl1, pl4cl2, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-Coumarate:coenzyme A ligase
-
-
-
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4-coumaroyl-CoA synthase
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-
-
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4-Coumaryl-CoA synthetase
-
-
-
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4CL
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-
-
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Caffeolyl coenzyme A synthetase
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-
-
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Clone 4CL14
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-
-
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Clone 4CL16
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-
-
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Feruloyl CoA ligase
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-
-
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Feruloyl coenzyme A synthetase
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-
-
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Hydroxy-cinnamate:CoA ligase
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-
-
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Hydroxycinnamate:CoA ligase
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-
-
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Hydroxycinnamoyl CoA synthetase
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-
-
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p-Coumaroyl CoA ligase
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-
-
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p-Coumaryl coenzyme A synthetase
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-
-
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p-Coumaryl-CoA ligase
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-
-
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p-Coumaryl-CoA synthetase
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-
-
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p-Hydroxycinnamic acid:CoA ligase
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-
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p-Hydroxycinnamoyl coenzyme A synthetase
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-
-
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Sinapoyl coenzyme A snthetase
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-
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Synthetase, p-coumaroyl coenzyme A
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acid-thiol ligation
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-
-
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PATHWAY SOURCE
PATHWAYS
KEGG
-
-, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
4-coumarate:CoA ligase (AMP-forming)
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CAS REGISTRY NUMBER
COMMENTARY
37332-51-7
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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
ATP + 4-coumarate + CoA
?
-
enzyme has an important role in the determination of the composition and the amount of lignin in tobacco plants
-
-
?
ATP + cinnamic acid + CoA
AMP + diphosphate + cinnamoyl-CoA
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3-phenyl-2-propenoic acid, 98%
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-
?
ATP + ferulic acid + CoA
AMP + diphosphate + 4-feruloyl-CoA
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4-hydroxy-3-methoxycinnamic acid, 99%
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-
?
ATP + sinapic acid + CoA
AMP + diphosphate + 4-sinapoyl-CoA
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3,5-dimethoxy-4-hydroxycinnamic acid, 98%, predominantly trans isomer
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-
?
ATP + 4-coumarate + CoA
AMP + diphosphate + 4-coumaroyl-CoA
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-
-
-
?
ATP + 4-coumarate + CoA
AMP + diphosphate + 4-coumaroyl-CoA
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the enzyme is involved in the phenylpropanoid pathway
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-
?
ATP + 4-coumarate + CoA
AMP + diphosphate + 4-coumaroyl-CoA
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4-hydroxycinnamic acid, 98%, predominantly trans-isomer
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-
?
ATP + caffeic acid + CoA
AMP + diphosphate + caffeoyl-CoA
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3,4-dihydroxycinnamic acid, 98%
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-
?
ATP + caffeic acid + CoA
AMP + diphosphate + caffeoyl-CoA
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3,4-dihydroxycinnamic acid, 98%, predominantly trans-isomer
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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
ATP + 4-coumarate + CoA
?
-
enzyme has an important role in the determination of the composition and the amount of lignin in tobacco plants
-
-
?
ATP + 4-coumarate + CoA
AMP + diphosphate + 4-coumaroyl-CoA
-
the enzyme is involved in the phenylpropanoid pathway
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
propanil
-
a herbicide, 71.8% inhibition at 0.1 mM, uncompetitive inhibition towards 4-coumaric acid
swep
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a herbicide, 97.1% inhibition at 0.1 mM, uncompetitive inhibition towards 4-coumaric acid
additional information
-
development and optimization of a high-throughput miniaturized screening system of plant growth inhibitors targeting 4CL in the phenylpropanoid pathway, in vitro inhibitor screening using 28 existing herbicides, overview, no inhibition by pendimethalin, trifluralin, alloxydim-sodium, bispyribac-sodium, dimethenamid, metolachlor, pyrazolate, bensulfuron-methyl, and imazosulfuron
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additional information
-
in vitro inhibitor screening using existing herbicides, screening assay optimization, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
kinetics in presence of inhibitors
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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). 4CL2_TOBAC
542
0
59480
Swiss-Prot
other Location (Reliability: 3)
PDB
SCOP
CATH
UNIPROT
ORGANISM
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
isoform 4CL2 in complex with Mg2+ and ATP or with AMP and coenzyme A or with three different hydroxycinnamate-AMP intermediates: 4-coumaroyl-AMP, caffeoyl-AMP, and feruloyl-AMP, hanging drop vapor diffusion method, using 20% (w/v) PEG 3350 and 0.2 M potassium nitrate or 4.4% (w/v) PEG 8000, 0.08 M sodium cacodylate (pH 6.5), 0.16 M calcium acetate, and 20% (v/v) glycerol or 25.5% (w/v) PEG 8000, 0.085 M sodium cacodylate (pH 6.5), 0.17 M sodium acetate, and 15% (v/v) glycerol or 25% (w/v) PEG 3350, 0.2 M ammonium acetate, and 0.1 M Tris (pH 8.5)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H237A
the mutant shows reduced activity compared to the wild type enzyme
K197A
the mutant shows reduced activity compared to the wild type enzyme
K443A
the mutant shows reduced activity compared to the wild type enzyme
M344A
the mutant shows reduced activity compared to the wild type enzyme
R435A
the mutant shows reduced activity compared to the wild type enzyme
T193A
the mutant shows reduced activity compared to the wild type enzyme
T336A
the mutant shows reduced activity compared to the wild type enzyme
Y239A
the mutant shows reduced activity compared to the wild type enzyme
Y239F
the mutant shows reduced activity compared to the wild type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme 6.3fold from Escherichia coli strain JM105 by a multistep process involving anion exchange chromatography and gel filtration
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recombinant enzyme from Escherichia coli strain JM105 by a multistep process involving anion exchange chromatography and gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae and Escherichia coli strain BL21, co-expression with stilbene synthase, gene STS, from Vitis vinifera establishing an resveratrol expression system with 4-coumaric acid as precursor, biosynthetic pathway of resveratrol, overview
gene 4CL, DNA and amino acid sequence determination and analysis, expression in Escherichia coli strain JM105
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
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the enzyme is a target for developing effective plant growth inhibitors, overview
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kajita, S.; Katayama, Y.; Omori, S.
Alterations in the biosynthesis of lignin in transgenic plants with chimeric genes for 4-coumarate:coenzyme A ligase
Plant Cell Physiol.
37
957-965
1996
Nicotiana tabacum
Lee, D.; Douglas, C.J.
Two divergent members of a tobacco 4-coumarate:coenzyme A ligase (4CL) gene family. cDNA structure, gene inheritance and expression, and properties of recombinant proteins
Plant Physiol.
112
193-205
1996
Nicotiana tabacum
Beekwilder, J.; Wolswinkel, R.; Jonker, H.; Hall, R.; de Vos, C.H.; Bovy, A.
Production of resveratrol in recombinant microorganisms
Appl. Environ. Microbiol.
72
5670-5672
2006
Nicotiana tabacum (O24146), Nicotiana tabacum
Yun, M.S.; Chen, W.; Deng, F.; Kiyokawa, T.; Mametsuka, K.; Yogo, Y.
An in vitro screening assay to discover novel inhibitors of 4-coumarate:CoA ligase
Pest Manag. Sci.
62
1065-1071
2006
Nicotiana tabacum
Yun, M.S.; Chen, W.; Deng, F.; Yogo, Y.
Propanil and swep inhibit 4-coumarate:CoA ligase activity in vitro
Pest Manag. Sci.
63
815-820
2007
Nicotiana tabacum
EXTERNAL LINKS (specific for EC-Number 6.2.1.12)
Transporter Classification Database (TCDB): 4.C.1.1.7
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