Coumaroyl-CoA: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 426717604

| Name = Coumaroyl-Coenzyme A

| ImageFile = 4-Coumaroyl-CoA.svg

| ImageSize = 250px

| IUPACName = 3′-''O''-Phosphonoadenosine 5′-[(3''R'')-3-hydroxy-4-({3-[(2-<nowiki/>{[(2''E'')-3-(4-hydroxyphenyl)prop-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]

| SystematicName = [(2''R'',3''S'',4''R'',5''R'')-5-(6-Amino-9''H''-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl (3''R'')-3-hydroxy-4-({3-[(2-<nowiki/>{[(2''E'')-3-(4-hydroxyphenyl)prop-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate

| OtherNames = [[4-Coumaroyl]]-[[Coenzyme A|CoA]]<br>p-Coumaroyl-CoA<br>4-Hydroxycinnamoyl-CoA

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 119785-99-8

| PubChem = 6440013

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4944344

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C00223

| SMILES = CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSC(=O)/C=C/C4=CC=C(C=C4)O)O

| InChI = 1/C30H42N7O18P3S/c1-30(2,25(42)28(43)33-10-9-20(39)32-11-12-59-21(40)8-5-17-3-6-18(38)7-4-17)14-52-58(49,50)55-57(47,48)51-13-19-24(54-56(44,45)46)23(41)29(53-19)37-16-36-22-26(31)34-15-35-27(22)37/h3-8,15-16,19,23-25,29,38,41-42H,9-14H2,1-2H3,(H,32,39)(H,33,43)(H,47,48)(H,49,50)(H2,31,34,35)(H2,44,45,46)/b8-5+/t19-,23-,24-,25+,29-/m1/s1

| InChIKey = DMZOKBALNZWDKI-MATMFAIHBG

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C30H42N7O18P3S/c1-30(2,25(42)28(43)33-10-9-20(39)32-11-12-59-21(40)8-5-17-3-6-18(38)7-4-17)14-52-58(49,50)55-57(47,48)51-13-19-24(54-56(44,45)46)23(41)29(53-19)37-16-36-22-26(31)34-15-35-27(22)37/h3-8,15-16,19,23-25,29,38,41-42H,9-14H2,1-2H3,(H,32,39)(H,33,43)(H,47,48)(H,49,50)(H2,31,34,35)(H2,44,45,46)/b8-5+/t19-,23-,24-,25+,29-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DMZOKBALNZWDKI-MATMFAIHSA-N

| MeSHName =

|Section2={{Chembox Properties

| Formula = C₃₀H₄₂N₇O₁₈P₃S

| MolarMass = 913.67 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''Coumaroyl-coenzyme A''' is the [[thioester]] of [[coenzyme-A]] and [[coumaric acid]]. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include [[Monolignol|lignols]] (precursors to [[lignin]] and [[lignocellulose]]), [[flavonoids]], [[isoflavonoids]], [[coumarin]]s, [[aurones]], [[stilbenes]], [[catechin]], and other [[phenylpropanoid]]s.<ref>{{cite journal|journal=Molecular Plant|year=2010|pages=2–20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|author=Vogt, T.|pmid=20035037|volume=3|doi-access=free}}</ref>

==Biosynthesis and significance==

It is generated in nature from [[phenylalanine]], which is converted by [[Phenylalanine ammonia-lyase|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 <math>\rightleftharpoons</math> AMP + diphosphate + 4-coumaroyl-CoA.

== Enzymes using Coumaroyl-Coenzyme A ==

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

* [[Anthocyanin 5-aromatic acyltransferase]]

* [[4-Coumarate-CoA ligase]]

* [[6'-Deoxychalcone synthase]]

== References ==

{{Hydroxycinnamic acid}}

[[Category:Thioesters of coenzyme A]]

[[Category:Hydroxycinnamic acid esters]]

{{Aromatic-stub}}