Coumaroyl-CoA: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~406237041~~
			\| Watchedfields = changed
⚫	\| Name = Coumaroyl-Coenzyme A
		⚫	\| verifiedrevid = 426717604
⚫	\| ImageFile = 4-Coumaroyl-CoA.svg
		⚫	\| Name = Coumaroyl-Coenzyme A
⚫	\| ImageSize = 250px
		⚫	\| ImageFile = 4-Coumaroyl-CoA.svg
	\| IUPACName = <nowiki>S-methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,
		⚫	\| ImageSize = 250px
	3-dimethylbutanoyl]amino]propanoylamino]ethyl](E)-3-(4-hydroxyphenyl)prop-2-enethioate</nowiki>
			\| IUPACName = 3′-''O''-Phosphonoadenosine 5′-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]
⚫	\| OtherNames = 4-~~]-]<br>p-Coumaroyl-CoA<br>4-Hydroxycinnamoyl-CoA~~
			\| SystematicName = methyl (3''R'')-3-hydroxy-4-({3-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| OtherNames = ]-]<br>p-Coumaroyl-CoA<br>4-Hydroxycinnamoyl-CoA
⚫	\| CASNo = 119785-99-8
		⚫	\|Section1={{Chembox Identifiers
⚫	\| PubChem = ~~5280329~~
			\| CASNo_Ref = {{cascite\|correct\|??}}
⚫	\| SMILES = CC(C)(COP(=O)(O)OP(=O)(O)~~OCC1C~~(C(C(O1)N2C=NC3=~~C2N~~=CN=~~C3N~~)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)C=~~CC4~~=CC=C(C=C4)O)O
		⚫	\| CASNo = 119785-99-8
⚫	\| MeSHName =
		⚫	\| 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)OC1(((O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)(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		\|Section2={{Chembox Properties
	\| Formula = C<sub>30</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S		\| Formula = C<sub>30</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S
	\| MolarMass = 913.67 g/mol		\| MolarMass = 913.67 g/mol
			\| Appearance =
	\| ExactMass = 913.151988
	\| ~~Appearance~~ =		\| Density =
	\| ~~Density~~ =		\| MeltingPt =
	\| ~~MeltingPt~~ =		\| BoilingPt =
	\| BoilingPt =
	}}		}}
	\| Section3 = {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| ~~Solubility~~ =		\| MainHazards =
	\| ~~MainHazards~~ =		\| FlashPt =
	\| ~~FlashPt~~ =		\| AutoignitionPt =
	\| Autoignition =
	}}		}}
	}}		}}
			'''Coumaroyl-coenzyme A''' is the ] of ] and ]. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include ] (precursors to ] and ]), ], ], ]s, ], ], ], and other ]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>
	'''Coumaroyl-Coenzyme A''' is a chemical compound used in ] production, a key compound in the ]s and ]s biosynthesis pathways in plants.

			==Biosynthesis and significance==
	] is also synthetized via coumaroyl-coA<ref></ref>.
			It is generated in nature from ], which is converted by ] to trans-]. Trans-cinnamate is hydroxylated by ] to give 4-hydroxycinnamate (i.e, coumarate). Coumarate is condensed with coenzyme-A in the presence of ]:
			:ATP + 4-coumarate + CoA <math>\rightleftharpoons</math> AMP + diphosphate + 4-coumaroyl-CoA.

	==Enzymes using Coumaroyl-Coenzyme A==		== Enzymes using Coumaroyl-Coenzyme A ==
			* ]
			* ]
	* ]		* ]
	* ]		* ]
	* ]		* ]
	* ]		* ]
	* ]		* ]
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	* ]		* ]

	==References==		== References ==
	{{reflist}}		{{reflist}}

			{{Hydroxycinnamic acid}}

	{{DEFAULTSORT:Coumaroyl-Coa}}		{{DEFAULTSORT:Coumaroyl-Coa}}
	]		]
			]

			{{Aromatic-stub}}

	{{organic-compound-stub}}

	]
	]

Latest revision as of 19:56, 20 December 2023

Coumaroyl-Coenzyme A
Names

IUPAC name 3′-O-Phosphonoadenosine 5′-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name methyl (3R)-3-hydroxy-4-({3-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
Other names 4-Coumaroyl-CoA p-Coumaroyl-CoA 4-Hydroxycinnamoyl-CoA
Identifiers
CAS Number	119785-99-8
3D model (JSmol)	Interactive image
ChemSpider	4944344
KEGG	C00223
PubChem CID	6440013
CompTox Dashboard (EPA)	DTXSID001028841
InChI InChI=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/s1Key: DMZOKBALNZWDKI-MATMFAIHSA-N 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/s1Key: DMZOKBALNZWDKI-MATMFAIHBG
SMILES CC(C)(COP(=O)(O)OP(=O)(O)OC1(((O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)(C(=O)NCCC(=O)NCCSC(=O)/C=C/C4=CC=C(C=C4)O)O
Properties
Chemical formula	C₃₀H₄₂N₇O₁₈P₃S
Molar mass	913.67 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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 lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids.

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

\rightleftharpoons

AMP + diphosphate + 4-coumaroyl-CoA.

Enzymes using Coumaroyl-Coenzyme A

References

Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–20. doi:10.1093/mp/ssp106. PMID 20035037.

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Tartaric acid esters

Caftaric acid
Chicoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C, F
Chiritoside A, B, C
Cistanoside A, B, C, D, E, F, G, H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-O-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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