Coumaroyl-CoA
Coumaroyl-coenzyme A is a chemical compound found in plants. The compound is the thioester of coenzyme-A and coumaric acid.
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IUPAC name
S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,
3-dimethylbutanoyl]amino]propanoylamino]ethyl](E)-3-(4-hydroxyphenyl)prop-2-enethioate | |
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Properties | |
C30H42N7O18P3S | |
Molar mass | 913.67 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Biosynthesis and significance
It is generated in nature from phenylalanine, which is converted by PAL to trans-cinnamate. Trans-cinnamate is hydroxylated by trans-cinnamate 4-monooxygenase to give 4-hydroxycinnamate (i.e, coumarate). Coumarate is condensed with coenzyme-A in the presence of 4-coumarate-CoA ligase:
- ATP + 4-coumarate + CoA AMP + diphosphate + 4-coumaroyl-CoA.
Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids.[1]
Enzymes using Coumaroyl-Coenzyme A
- Anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase
- Anthocyanin 5-aromatic acyltransferase
- Chalcone synthase
- 4-Coumarate-CoA ligase
- 6'-Deoxychalcone synthase
- Agmatine N4-coumaroyltransferase
- Flavonol-3-O-triglucoside O-coumaroyltransferase
- Naringenin-chalcone synthase
- Shikimate O-hydroxycinnamoyltransferase
- Trihydroxystilbene synthase
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References
- Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
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