Coumaroyl-coenzyme A is the thioester of

coenzyme-A Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All genomes sequenced to date encode enzymes that use coenzyme A as a substr ...

and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols (precursors to

lignin Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity ...

and lignocellulose), flavonoids,

isoflavonoids Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estro ...

, coumarins, aurones,

stilbenes Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are pro ...

, catechin, and other

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

Biosynthesis and significance

It is generated in nature from

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

, 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

\rightleftharpoons

AMP + diphosphate + 4-coumaroyl-CoA.

Enzymes using Coumaroyl-Coenzyme A

* Anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase *

Anthocyanin 5-aromatic acyltransferase In enzymology, an anthocyanin 5-aromatic acyltransferase () is an enzyme that catalyzes the chemical reaction :hydroxycinnamoyl-CoA + anthocyanidin-3,5-diglucoside \rightleftharpoons CoA + anthocyanidin 3-glucoside-5-hydroxycinnamoylglucoside Thu ...

* Chalcone synthase * 4-Coumarate-CoA ligase *

6'-Deoxychalcone synthase In enzymology, a 6'-deoxychalcone synthase () is an enzyme that catalyzes the chemical reaction :3 malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ \rightleftharpoons 4 CoA + isoliquiritigenin + 3 CO2 + NADP+ + H2O The 4 substrates of this enzyme are ...

Agmatine N4-coumaroyltransferase In enzymology, an agmatine N4-coumaroyltransferase () is an enzyme that catalyzes the chemical reaction :4-coumaroyl-CoA + agmatine \rightleftharpoons CoA + N-(4-guanidinobutyl)-4-hydroxycinnamamide Thus, the two substrates of this enzyme are 4- ...

Flavonol-3-O-triglucoside O-coumaroyltransferase In enzymology, a flavonol-3-O-triglucoside O-coumaroyltransferase () is an enzyme that catalyzes the chemical reaction :4-coumaroyl-CoA + a flavonol 3-O- 2)-beta-D-glucosyl-(1->2)-beta-D-glucoside.html" ;"title="eta-D-glucosyl-(1->2)-beta-D-glucos ...

Naringenin-chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a ...

Shikimate O-hydroxycinnamoyltransferase In enzymology, a shikimate O-hydroxycinnamoyltransferase () is an enzyme that catalyzes the chemical reaction :4-coumaroyl-CoA + shikimate \rightleftharpoons CoA + 4-coumaroylshikimate Thus, the two substrates of this enzyme are 4-coumaroyl-CoA ...

* Trihydroxystilbene synthase

References

Thioesters of coenzyme A Hydroxycinnamic acid esters Vinylogous carboxylic acids {{Aromatic-stub