Acetyl-CoA

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Acetyl-CoA

Names
Preferred IUPAC name O1-{(3R)-4-[(3-{[2-(Acetylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} O3-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} dihydrogen diphosphate
Identifiers
CAS Number	72-89-9 (free acid) Y
3D model ( JSmol )	Interactive image Interactive image
ChEBI	CHEBI:15351 Y
ChemSpider	392413 Y
ECHA InfoCard	100.000.719
IUPHAR/BPS	3038
KEGG	C00024 N
MeSH	Acetyl+Coenzyme+A
PubChem CID	444493
UNII	76Q83YLO3O Y
CompTox Dashboard (EPA)	DTXSID30992686
InChI InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Y Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N Y InChI=1/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Key: ZSLZBFCDCINBPY-ZSJPKINUBJ
SMILES O=C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O)C CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O
Properties
Chemical formula	C23H38N7O17P3S
Molar mass	809.57 g·mol−1
UV-vis (λmax)	260 nm; 232 nm[1]
Absorbance	ε232 on thioester hydrolysis = −4.5 mM−1 cm−1[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many

CoA is acetylated to acetyl-CoA by the breakdown of

In addition, acetyl-CoA is a precursor for the biosynthesis of various acetyl-chemicals, acting as an intermediate to transfer an acetyl group during the biosynthesis of those acetyl-chemicals. Acetyl-CoA is also involved in the regulation of various cellular mechanisms by providing acetyl groups to target amino acid residues for post-translational acetylation reactions of proteins.^[7]

Biosynthesis

The acetylation of CoA is determined by the carbon sources.^[8][9]

Extramitochondrial

• At high
  ATP citrate lyase (ACL). This principal reaction is coupled with the hydrolysis of ATP.^[10][11]
• At low glucose levels:
  • CoA is acetylated using acetate by acetyl-CoA synthetase (ACS), also coupled with ATP hydrolysis.^[12]
  • Ethanol also serves as a carbon source for acetylation of CoA utilizing the enzyme alcohol dehydrogenase.^[13]
  • Degradation of branched-chain
    acetoacetate.^{[14][page needed}
    ]

• At high glucose levels, acetyl-CoA is produced through
  disproportionates pyruvate into acetyl-CoA and formic acid
  .

• At low glucose levels, the production of acetyl-CoA is linked to
  oxidation and thiolysis catalyzed by four respective enzymes, namely acyl-CoA dehydrogenase, enoyl-CoA hydratase, 3-hydroxyacyl-CoA dehydrogenase, and thiolase. The cycle produces a new fatty acid chain with two fewer carbons and acetyl-CoA as a byproduct.^[16]

• In cellular respiration
• Citric acid cycle:
  • Through a series of chemical reactions, stored energy is released through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins into adenosine triphosphate (ATP) and carbon dioxide.
• Fatty acid metabolism
  • Acetyl-CoA is produced by the breakdown of both
    lipids (by β-oxidation). It then enters the citric acid cycle in the mitochondrion by combining with oxaloacetate to form citrate.^[17][18]
  • Two acetyl-CoA molecules condense to form
    β-hydroxybutyrate.^[17] Acetoacetate, β-hydroxybutyrate, and their spontaneous breakdown product acetone^[19] are frequently, but confusingly, known as ketone bodies (as they are not "bodies" at all, but water-soluble chemical substances). The ketone bodies are released by the liver into the blood. All cells with mitochondria can take ketone bodies up from the blood and reconvert them into acetyl-CoA, which can then be used as fuel in their citric acid cycles, as no other tissue can divert its oxaloacetate into the gluconeogenic pathway in the way that the liver does. Unlike free fatty acids, ketone bodies can cross the blood–brain barrier and are therefore available as fuel for the cells of the central nervous system, acting as a substitute for glucose, on which these cells normally survive.^[17] The occurrence of high levels of ketone bodies in the blood during starvation, a low-carbohydrate diet, prolonged heavy exercise, and uncontrolled type-1 diabetes mellitus is known as ketosis, and in its extreme form in out-of-control type-1 diabetes mellitus, as ketoacidosis
    .
  • On the other hand, when the
    cellular membranes.^[17]
  • In plants, de novo fatty acid synthesis occurs in the plastids. Many seeds accumulate large reservoirs of seed oils to support germination and early growth of the seedling before it is a net photosynthetic organism.
  • The
    bile salts, and vitamin D.^[17][21]
  • Acetyl-CoA can be
    malonation of proteins and other phytochemicals.^[22] In plants, these include sesquiterpenes, brassinosteroids (hormones), and membrane sterols
    .
• Steroid synthesis
  :
  • Acetyl-CoA participates in the mevalonate pathway by partaking in the synthesis of hydroxymethyl glutaryl-CoA.
• Acetylcholine synthesis:
  • Acetyl-CoA is also an important component in the biogenic synthesis of the neurotransmitter acetylcholine. Choline, in combination with acetyl-CoA, is catalyzed by the enzyme choline acetyltransferase to produce acetylcholine and coenzyme A as a byproduct.
• Melatonin synthesis
• Acetylation
  • Acetyl-CoA is also the source of the acetyl group incorporated onto certain
    acetyltransferases. This acetylation affects cell growth, mitosis, and apoptosis.^[23]
• Allosteric regulator
  • Acetyl-CoA serves as an allosteric regulator of pyruvate dehydrogenase kinase (PDK). It regulates through the ratio of acetyl-CoA versus CoA. Increased concentration of acetyl-CoA activates PDK.^[24]
  • Acetyl-CoA is also an allosteric activator of pyruvate carboxylase.^[25]

Interactive pathway map

Click on genes, proteins and metabolites below to visit

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See also

• Malonyl-CoA decarboxylase

References