EC |
2.3.1.91 |
Accepted name: |
sinapoylglucose—choline O-sinapoyltransferase |
Reaction: |
1-O-sinapoyl-β-D-glucose + choline = D-glucose + sinapoylcholine |
Glossary: |
sinapoyl = 4-hydroxy-3,5-dimethoxycinnamoyl |
Other name(s): |
sinapine synthase |
Systematic name: |
1-O-sinapoyl-β-D-glucose:choline 1-O-sinapoyltransferase |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 85205-00-1 |
References: |
1. |
Gräwe, W. and Strack, D. Partial-purification and some properties of 1-sinapoylglucose-choline sinapoyltransferase (sinapine synthase) from seeds of Raphanus sativus L. and Sinapis alba L. Z. Naturforsch. C: Biosci. 41 (1986) 28–33. |
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[EC 2.3.1.91 created 1986] |
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EC |
2.3.1.92 |
Accepted name: |
sinapoylglucose—malate O-sinapoyltransferase |
Reaction: |
1-O-sinapoyl-β-D-glucose + (S)-malate = D-glucose + sinapoyl-(S)-malate |
Other name(s): |
1-sinapoylglucose-L-malate sinapoyltransferase; sinapoylglucose:malate sinapoyltransferase |
Systematic name: |
1-O-sinapoyl-β-D-glucose:(S)-malate O-sinapoyltransferase |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 76095-65-3 |
References: |
1. |
Strack, D. Development of 1-O-sinapoyl-β-D-glucose-l-malate sinapoyltransferase activity in cotyledons of red radish (Raphanus sativus L. var sativus). Planta 155 (1982) 31–36. [PMID: 24271623] |
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[EC 2.3.1.92 created 1986] |
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EC |
2.3.1.103 |
Accepted name: |
sinapoylglucose—sinapoylglucose O-sinapoyltransferase |
Reaction: |
2 1-O-sinapoyl-β-D-glucose = D-glucose + 1,2-bis-O-sinapoyl-β-D-glucose |
Glossary: |
1-O-sinapoyl-β-D-glucose = 1-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-propenoyl]-β-D-glucopyranose |
Other name(s): |
hydroxycinnamoylglucose-hydroxycinnamoylglucose hydroxycinnamoyltransferase; 1-(hydroxycinnamoyl)-glucose:1-(hydroxycinnamoyl)-glucose hydroxycinnamoyltransferase; 1-O-(4-hydroxy-3,5-dimethoxycinnamoyl)-β-D-glucoside:1-O-(4-hydroxy-3,5-dimethoxycinnamoyl)-β-D-glucoside 1-O-sinapoyltransferase |
Systematic name: |
1-O-sinapoyl-β-D-glucose:1-O-sinnapoyl-β-D-glucose 1-O-sinapoyltransferase |
Comments: |
The plant enzyme, characterized from Brassicaceae, is involved in secondary metabolism. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 103537-11-7 |
References: |
1. |
Dahlbender, B. and Strack, D. Purification and properties of 1-(hydroxycinnamoyl)-glucose-1-(hydroxycinnamoyl)-glucose hydroxycinnamoyl-transferase from radish seedlings. Phytochemistry 25 (1986) 1043–1046. |
2. |
Fraser, C.M., Thompson, M.G., Shirley, A.M., Ralph, J., Schoenherr, J.A., Sinlapadech, T., Hall, M.C. and Chapple, C. Related Arabidopsis serine carboxypeptidase-like sinapoylglucose acyltransferases display distinct but overlapping substrate specificities. Plant Physiol. 144 (2007) 1986–1999. [PMID: 17600138] |
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[EC 2.3.1.103 created 1989] |
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EC |
2.3.1.106 |
Accepted name: |
tartronate O-hydroxycinnamoyltransferase |
Reaction: |
sinapoyl-CoA + 2-hydroxymalonate = CoA + sinapoyltartronate |
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For diagram of reaction, click here |
Glossary: |
sinapate = 4-hydroxy-3,5-dimethoxycinnamate
tartronate = 2-hydroxymalonate |
Other name(s): |
tartronate sinapoyltransferase; hydroxycinnamoyl-coenzyme-A:tartronate hydroxycinnamoyltransferase |
Systematic name: |
sinapoyl-CoA:2-hydroxymalonate O-(hydroxycinnamoyl)transferase |
Comments: |
4-Coumaroyl-CoA (4-hydroxycinnamoyl-CoA), caffeoyl-CoA (3,4-dihydroxycinnamoyl-CoA) and feruloyl-CoA (4-hydroxy-3-methoxycinnamoyl-CoA) can also act as donors for the enzyme from the mung bean (Vigna radiata). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 102484-57-1 |
References: |
1. |
Strack, D., Ruhoff, R. and Gräwe, W. Hydroxycinnamoyl-Coenzyme-A-tartronate hydroxycinnamoyltransferase in protein preparations from mung bean. Phytochemistry 25 (1986) 833–837. |
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[EC 2.3.1.106 created 1989, modified 1990, modified 2002] |
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EC |
2.3.1.110 |
Accepted name: |
tyramine N-feruloyltransferase |
Reaction: |
feruloyl-CoA + tyramine = CoA + N-feruloyltyramine |
Other name(s): |
tyramine N-feruloyl-CoA transferase; feruloyltyramine synthase; feruloyl-CoA tyramine N-feruloyl-CoA transferase; tyramine feruloyltransferase |
Systematic name: |
feruloyl-CoA:tyramine N-(hydroxycinnamoyl)transferase |
Comments: |
Cinnamoyl-CoA, 4-coumaroyl-CoA and sinapoyl-CoA can also act as donors, and some aromatic amines can act as acceptors. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 128909-19-3 |
References: |
1. |
Negrel, J. and Martin, C. The biosynthesis of feruloyltyramine in Nicotiana tabacum. Phytochemistry 23 (1984) 2797–2801. |
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[EC 2.3.1.110 created 1989] |
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EC |
2.3.1.130 |
Accepted name: |
galactarate O-hydroxycinnamoyltransferase |
Reaction: |
feruloyl-CoA + galactarate = CoA + O-feruloylgalactarate |
Other name(s): |
galacturate hydroxycinnamoyltransferase |
Systematic name: |
feruloyl-CoA:galactarate O-(hydroxycinnamoyl)transferase |
Comments: |
Sinapoyl-CoA and 4-coumaroyl-CoA can also act as donors. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 112956-50-0 |
References: |
1. |
Strack, D., Keller, H. and Weissenböck, G. Enzymatic-synthesis of hydroxycinnamic acid-esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves. J. Plant Physiol. 131 (1987) 61–73. |
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[EC 2.3.1.130 created 1990] |
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EC |
2.3.1.131 |
Accepted name: |
glucarate O-hydroxycinnamoyltransferase |
Reaction: |
sinapoyl-CoA + glucarate = CoA + O-sinapoylglucarate |
Systematic name: |
sinapoyl-CoA:glucarate O-(hydroxycinnamoyl)transferase |
Comments: |
4-Coumaroyl-CoA, feruloyl-CoA and caffeoyl-CoA can also act as donors, but more slowly. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 112956-51-1 |
References: |
1. |
Strack, D., Keller, H. and Weissenböck, G. Enzymatic-synthesis of hydroxycinnamic acid-esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves. J. Plant Physiol. 131 (1987) 61–73. |
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[EC 2.3.1.131 created 1990] |
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EC |
2.3.1.132 |
Accepted name: |
glucarolactone O-hydroxycinnamoyltransferase |
Reaction: |
sinapoyl-CoA + glucarolactone = CoA + O-sinapoylglucarolactone |
Systematic name: |
sinapoyl-CoA:glucarolactone O-(hydroxycinnamoyl)transferase |
Comments: |
4-Coumaroyl-CoA, feruloyl-CoA and caffeoyl-CoA can also act as donors, but more slowly. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 112956-52-2 |
References: |
1. |
Strack, D., Keller, H. and Weissenböck, G. Enzymatic-synthesis of hydroxycinnamic acid-esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves. J. Plant Physiol. 131 (1987) 61–73. |
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[EC 2.3.1.132 created 1990] |
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EC |
2.3.1.133 |
Accepted name: |
shikimate O-hydroxycinnamoyltransferase |
Reaction: |
4-coumaroyl-CoA + shikimate = CoA + 4-coumaroylshikimate |
Other name(s): |
shikimate hydroxycinnamoyltransferase |
Systematic name: |
4-coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase |
Comments: |
Caffeoyl-CoA, feruloyl-CoA and sinapoyl-CoA can also act as donors, but more slowly. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 73904-44-6 |
References: |
1. |
Strack, D., Keller, H. and Weissenböck, G. Enzymatic-synthesis of hydroxycinnamic acid-esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves. J. Plant Physiol. 131 (1987) 61–73. |
2. |
Ulbrich, B. and Zenk, M.H. Partial purification and properties of p-hydroxycinnamoyl-CoA:shikimate-p-hydroxycinnamoyl transferase from higher plants. Phytochemistry 19 (1980) 1625–1629. |
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[EC 2.3.1.133 created 1990] |
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EC |
2.3.1.138 |
Accepted name: |
putrescine N-hydroxycinnamoyltransferase |
Reaction: |
caffeoyl-CoA + putrescine = CoA + N-caffeoylputrescine |
Glossary: |
putrescine = butane-1,4-diamine |
Other name(s): |
caffeoyl-CoA putrescine N-caffeoyl transferase; PHT; putrescine hydroxycinnamoyl transferase; hydroxycinnamoyl-CoA:putrescine hydroxycinnamoyltransferase; putrescine hydroxycinnamoyltransferase |
Systematic name: |
caffeoyl-CoA:putrescine N-(3,4-dihydroxycinnamoyl)transferase |
Comments: |
Feruloyl-CoA, cinnamoyl-CoA and sinapoyl-CoA can also act as donors, but more slowly. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 120598-69-8 |
References: |
1. |
Negrel, J. The biosynthesis of cinnamoylputrescines in callus-tissue cultures of Nicotiana tabacum. Phytochemistry 28 (1989) 477–481. |
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[EC 2.3.1.138 created 1992] |
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EC |
2.3.1.188 |
Accepted name: |
ω-hydroxypalmitate O-feruloyl transferase |
Reaction: |
feruloyl-CoA + 16-hydroxypalmitate = CoA + 16-feruloyloxypalmitate |
Other name(s): |
hydroxycinnamoyl-CoA ω-hydroxypalmitic acid O-hydroxycinnamoyltransferase; HHT |
Systematic name: |
feruloyl-CoA:16-hydroxypalmitate feruloyltransferase |
Comments: |
p-Coumaroyl-CoA and sinapoyl-CoA also act as substrates. The enzyme is widely distributed in roots of higher plants. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Lotfy, S., Negrel, J. and Javelle, F. Formation of feruloyloxypalmitic acid by an enzyme from wound-healing potato tuber discs. Phytochemistry 35 (1994) 1419–1424. |
2. |
Lotfy, S. Javelle, F. and Negrel, J. Distribution of hydroxycinnamoyl-CoA ω-hydroxypalmitic acid O-hydroxycinnamoyltransferase in higher plants. Phytochemistry 40 (1995) 389–391. |
3. |
Lotfy, S. Javelle, F. and Negrel, J. Purification and characterization of hydroxycinnamoyl-CoA ω-hydroxypalmitic acid O-hydroxycinnamoyltransferase from tobacco (Nicotiana tabacum L.) cell-suspension cultures. Planta 199 (1996) 475–480. |
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[EC 2.3.1.188 created 2009] |
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EC |
2.3.1.213 |
Accepted name: |
cyanidin 3-O-(6-O-glucosyl-2-O-xylosylgalactoside) 6′′′-O-hydroxycinnamoyltransferase |
Reaction: |
1-O-(4-hydroxycinnamoyl)-β-D-glucose + cyanidin 3-O-(6-O-β-D-glucosyl-2-O-β-D-xylosyl-β-D-galactoside) = β-D-glucose + cyanidin 3-O-[6-O-(6-O-4-hydroxycinnamoyl-β-D-glucosyl)-2-O-β-D-xylosyl-β-D-galactoside] |
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For diagram of cyanidin galactoside biosynthesis, click here |
Glossary: |
1-O-(4-hydroxycinnamoyl)-β-D-glucose = 1-O-(4-coumaroyl)-β-D-glucose
cyanidin = 3,3′,4′,5,7-pentahydroxyflavylium |
Other name(s): |
1-O-(4-hydroxycinnamoyl)-β-D-glucose:cyanidin 3-O-(2"-O-xylosyl-6"-O-glucosylgalactoside) 6′′′-O-(4-hydroxycinnamoyl)transferase |
Systematic name: |
1-O-(4-hydroxycinnamoyl)-β-D-glucose:cyanidin 3-O-(6-O-β-D-glucosyl-2-O-β-D-xylosyl-β-D-galactoside) 6′′′-O-(4-hydroxycinnamoyl)transferase |
Comments: |
Isolated from the plant Daucus carota (Afghan cultivar carrot). In addition to 1-O-(4-hydroxycinnamoyl)-β-D-glucose, the enzyme can use the 1-O-sinapoyl- and 1-O-feruloyl- derivatives of β-D-glucose.
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Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Gläßgen, W.E. and Seitz, H.U. Acylation of anthocyanins with hydroxycinnamic acids via 1-O-acylglucosides by protein preparations from cell cultures of Daucus carota L. Planta 186 (1992) 582–585. [PMID: 24186789] |
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[EC 2.3.1.213 created 2013] |
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EC |
2.3.1.248 |
Accepted name: |
spermidine disinapoyl transferase |
Reaction: |
2 sinapoyl-CoA + spermidine = 2 CoA + N1,N8-bis(sinapoyl)-spermidine |
Other name(s): |
SDT |
Systematic name: |
sinapoyl-CoA:spermidine N-(hydroxycinnamoyl)transferase |
Comments: |
The enzyme from the plant Arabidopsis thaliana has no activity with 4-coumaroyl-CoA (cf. EC 2.3.1.249, spermidine dicoumaroyl transferase). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Luo, J., Fuell, C., Parr, A., Hill, L., Bailey, P., Elliott, K., Fairhurst, S.A., Martin, C. and Michael, A.J. A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 21 (2009) 318–333. [DOI] [PMID: 19168716] |
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[EC 2.3.1.248 created 2015] |
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EC |
2.3.1.249 |
Accepted name: |
spermidine dicoumaroyl transferase |
Reaction: |
2 4-coumaroyl-CoA + spermidine = 2 CoA + N1,N8-bis(4-coumaroyl)-spermidine |
Other name(s): |
SCT |
Systematic name: |
4-coumaroyl-CoA:spermidine N-(hydroxycinnamoyl)transferase |
Comments: |
The enzyme from the plant Arabidopsis thaliana has no activity with sinapoyl-CoA (cf. EC 2.3.1.248, spermidine disinapoyl transferase). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Luo, J., Fuell, C., Parr, A., Hill, L., Bailey, P., Elliott, K., Fairhurst, S.A., Martin, C. and Michael, A.J. A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 21 (2009) 318–333. [DOI] [PMID: 19168716] |
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[EC 2.3.1.249 created 2015] |
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EC |
2.4.1.120 |
Accepted name: |
sinapate 1-glucosyltransferase |
Reaction: |
UDP-α-D-glucose + sinapate = UDP + 1-O-sinapoyl-β-D-glucose |
Glossary: |
sinapate = (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate |
Other name(s): |
uridine diphosphoglucose-sinapate glucosyltransferase; UDP-glucose:sinapic acid glucosyltransferase; uridine 5′-diphosphoglucose-hydroxycinnamic acid acylglucosyltransferase; UDP-glucose:sinapate D-glucosyltransferase |
Systematic name: |
UDP-α-D-glucose:sinapate D-glucosyltransferase |
Comments: |
Some other hydroxycinnamates, including 4-coumarate, ferulate and caffeate, can act as acceptors, but more slowly. Only glucose esters, not glucosides, are formed (cf. EC 2.4.1.126 hydroxycinnamate 4-β-glucosyltransferase). |
Links to other databases: |
BRENDA, EXPASY, GTD, KEGG, MetaCyc, CAS registry number: 74082-53-4 |
References: |
1. |
Strack, D. Enzymatic synthesis of 1-sinapoylglucose from free sinapic acid and UDP-glucose by a cell free system from Raphanus sativus seedlings. Z. Naturforsch. C: Biosci. 35 (1980) 204–208. |
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[EC 2.4.1.120 created 1984] |
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EC |
2.4.1.299 |
Accepted name: |
cyanidin 3-O-glucoside 5-O-glucosyltransferase (acyl-glucose) |
Reaction: |
1-O-sinapoyl-β-D-glucose + cyanidin 3-O-β-D-glucoside = sinapate + cyanidin 3,5-di-O-β-D-glucoside |
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For diagram of anthocyanidin glucoside biosynthesis, click here |
Glossary: |
sinapate = 4-hydroxy-3,5-dimethoxycinnamate
cyanidin = 3,3′,4′,5,7-pentahydroxyflavylium
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Other name(s): |
AA5GT |
Systematic name: |
1-O-sinapoyl-β-D-glucose:cyanidin-3-O-β-D-glucoside 5-O-β-D-glucosyltransferase |
Comments: |
Isolated from the plant Dianthus caryophyllus (carnation). Also acts on other anthocyanidins and with other acyl-glucose donors. cf. EC 2.4.1.298, anthocyanidin 3-O-glucoside 5-O-glucosyltransferase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Matsuba, Y., Sasaki, N., Tera, M., Okamura, M., Abe, Y., Okamoto, E., Nakamura, H., Funabashi, H., Takatsu, M., Saito, M., Matsuoka, H., Nagasawa, K. and Ozeki, Y. A novel glucosylation reaction on anthocyanins catalyzed by acyl-glucose-dependent glucosyltransferase in the petals of carnation and delphinium. Plant Cell 22 (2010) 3374–3389. [DOI] [PMID: 20971893] |
2. |
Nishizaki, Y., Matsuba, Y., Okamoto, E., Okamura, M., Ozeki, Y. and Sasaki, N. Structure of the acyl-glucose-dependent anthocyanin 5-O-glucosyltransferase gene in carnations and its disruption by transposable elements in some varieties. Mol. Genet. Genomics 286 (2011) 383–394. [DOI] [PMID: 22048706] |
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[EC 2.4.1.299 created 2013] |
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EC |
3.1.1.49 |
Accepted name: |
sinapine esterase |
Reaction: |
sinapoylcholine + H2O = sinapate + choline |
Other name(s): |
aromatic choline esterase |
Systematic name: |
sinapoylcholine sinapohydrolase |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 72506-67-3 |
References: |
1. |
Nurmann, G. and Strack, D. Sinapine esterase. 1. Characterization of sinapine esterase from cotyledons of Raphanus sativus. Z. Naturforsch. C: Biosci. 34 (1979) 715–720. |
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[EC 3.1.1.49 created 1984] |
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EC |
6.2.1.12 |
Accepted name: |
4-coumarate—CoA ligase |
Reaction: |
ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA |
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For diagram of chalcone and stilbene biosynthesis, click here |
Glossary: |
4-coumarate = 3-(4-hydroxyphenyl)prop-2-enoate |
Other name(s): |
4-coumaroyl-CoA synthetase; p-coumaroyl CoA ligase; p-coumaryl coenzyme A synthetase; p-coumaryl-CoA synthetase; p-coumaryl-CoA ligase; feruloyl CoA ligase; hydroxycinnamoyl CoA synthetase; 4-coumarate:coenzyme A ligase; caffeolyl coenzyme A synthetase; p-hydroxycinnamoyl coenzyme A synthetase; feruloyl coenzyme A synthetase; sinapoyl coenzyme A synthetase; 4-coumaryl-CoA synthetase; hydroxycinnamate:CoA ligase; p-coumaryl-CoA ligase; p-hydroxycinnamic acid:CoA ligase; 4CL |
Systematic name: |
4-coumarate:CoA ligase (AMP-forming) |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 37332-51-7 |
References: |
1. |
Gross, G.G. and Zenk, M.H. Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissue of Forsythia. Eur. J. Biochem. 42 (1974) 453–459. [DOI] [PMID: 4364250] |
2. |
Lindl, T., Kreuzaler, F. and Hahlbrock, F. Synthesis of p-coumaroyl coenzyme A with a partially purified p-coumarate:CoA ligase from cell suspension cultures of soybean (Glycine max). Biochim. Biophys. Acta 302 (1973) 457–464. [DOI] [PMID: 4699252] |
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[EC 6.2.1.12 created 1976] |
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