11/8/24, 7:46 AM Acetyl-CoA - Wikipedia

Acetyl-CoA
Acetyl-CoA (acetyl coenzyme A) is a molecule that participates
Acetyl-CoA
in many biochemical reactions in protein, carbohydrate and lipid
metabolism.[2] Its main function is to deliver the acetyl group to
the citric acid cycle (Krebs cycle) to be oxidized for energy
production.

Coenzyme A (CoASH or CoA) consists of a β-mercaptoethylamine

group linked to pantothenic acid (vitamin B5) through an amide
linkage[3] and 3'-phosphorylated ADP. The acetyl group (indicated
in blue in the structural diagram on the right) of acetyl-CoA is
linked to the sulfhydryl substituent of the β-mercaptoethylamine
group. This thioester linkage is a "high energy" bond, which is
particularly reactive. Hydrolysis of the thioester bond is exergonic
(−31.5 kJ/mol).

CoA is acetylated to acetyl-CoA by the breakdown of carbohydrates

through glycolysis and by the breakdown of fatty acids through β-
oxidation. Acetyl-CoA then enters the citric acid cycle, where the
acetyl group is oxidized to carbon dioxide and water, and the
energy released is captured in the form of 11 ATP and one GTP per
Names
acetyl group.
Preferred IUPAC name
Konrad Bloch and Feodor Lynen were awarded the 1964 Nobel O1-{(3R)-4-[(3-{[2-
(Acetylsulfanyl)ethyl]amino}-3-
Prize in Physiology or Medicine for their discoveries linking acetyl-
oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-
CoA and fatty acid metabolism. Fritz Lipmann won the Nobel Prize oxobutyl} O3-{[(2R,3S,4R,5R)-5-(6-amino-9H-
in 1953 for his discovery of the cofactor coenzyme A.[4] purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-
2-yl]methyl} dihydrogen diphosphate
Identifiers
Role CAS Number 72-89-9 (https://commonchemi
stry.cas.org/detail?cas_rn=72-
Acetyl-CoA is a metabolic intermediate that is involved in many 89-9) (free acid)
metabolic pathways in an organism. It is produced during the
3D model (JSmol) Interactive image (https://che
breakdown of glucose, fatty acids, and amino acids, and is used in
mapps.stolaf.edu/jmol/jmol.ph
the synthesis of many other biomolecules, including cholesterol,
p?model=O%3DC%28SCCN
fatty acids, and ketone bodies. Acetyl-CoA is also a key molecule in
C%28%3DO%29CCNC%28%
the citric acid cycle, which is a series of chemical reactions that
3DO%29%5BC%40H%5D%2
occur in the mitochondria of cells and is responsible for generating
8O%29C%28C%29%28C%29
energy in the form of ATP.[5][6]
COP%28%3DO%29%28O%2
In addition, acetyl-CoA is a precursor for the biosynthesis of 9OP%28%3DO%29%28O%2
various acetyl-chemicals, acting as an intermediate to transfer an 9OC%5BC%40H%5D3O%5B
acetyl group during the biosynthesis of those acetyl-chemicals. C%40%40H%5D%28n2cnc1
c%28ncnc12%29N%29%5B
C%40H%5D%28O%29%5B

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11/8/24, 7:46 AM Acetyl-CoA - Wikipedia

Acetyl-CoA is also involved in the regulation of various cellular C%40%40H%5D3OP%28%3

mechanisms by providing acetyl groups to target amino acid DO%29%28O%29O%29C)
residues for post-translational acetylation reactions of proteins. Interactive image (https://che
mapps.stolaf.edu/jmol/jmol.ph
p?model=CC%28%3DO%29S
Biosynthesis CCNC%28%3DO%29CCNC%
28%3DO%29%5BC%40%40
The acetylation of CoA is determined by the carbon sources.[7][8] H%5D%28C%28C%29%28
C%29COP%28%3DO%29%2
8O%29OP%28%3DO%29%2
Extramitochondrial
8O%29OC%5BC%40%40H%
At high glucose levels, glycolysis takes place rapidly, thus 5D1%5BC%40H%5D%28%5
increasing the amount of citrate produced from the citric acid BC%40H%5D%28%5BC%4
cycle. This citrate is then exported to other organelles outside 0%40H%5D%28O1%29n2cnc
the mitochondria to be broken into acetyl-CoA and
3c2ncnc3N%29O%29OP%2
oxaloacetate by the enzyme ATP citrate lyase (ACL). This
8%3DO%29%28O%29O%29
principal reaction is coupled with the hydrolysis of ATP.[9][10]
O)
At low glucose levels:
ChEBI CHEBI:15351 (https://www.eb
CoA is acetylated using acetate by acetyl-CoA synthetase
i.ac.uk/chebi/searchId.do?che
(ACS), also coupled with ATP hydrolysis.[11]
biId=15351)
Ethanol also serves as a carbon source for acetylation of
CoA utilizing the enzyme alcohol dehydrogenase.[12] ChemSpider 392413 (https://www.chemspid
Degradation of branched-chain ketogenic amino acids such er.com/Chemical-Structure.39
as valine, leucine, and isoleucine occurs. These amino 2413.html)
acids are converted to α-ketoacids by transamination and ECHA InfoCard 100.000.719 (https://echa.euro
eventually to isovaleryl-CoA through oxidative
pa.eu/substance-information/-/
decarboxylation by an α-ketoacid dehydrogenase complex.
Isovaleryl-CoA undergoes dehydrogenation, carboxylation substanceinfo/100.000.719)
and hydration to form another CoA-derivative intermediate IUPHAR/BPS 3038 (http://www.guidetophar
before it is cleaved into acetyl-CoA and acetoacetate.[13] macology.org/GRAC/LigandDi
splayForward?tab=summary&l
igandId=3038)
Intramitochondrial
KEGG C00024 (https://www.kegg.jp/e
At high glucose levels, acetyl- ntry/C00024)
CoA is produced through
MeSH Acetyl+Coenzyme+A (https://w
glycolysis.[14] Pyruvate
undergoes oxidative ww.nlm.nih.gov/cgi/mesh/201
decarboxylation in which it 4/MB_cgi?mode=&term=Acety
loses its carboxyl group (as l+Coenzyme+A)
Pyruvate dehydrogenase complex
carbon dioxide) to form acetyl- PubChem CID
reaction 444493 (https://pubchem.ncbi.
CoA, giving off 33.5 kJ/mol of
energy. The oxidative nlm.nih.gov/compound/44449
conversion of pyruvate into 3)
acetyl-CoA is referred to as the pyruvate dehydrogenase UNII 76Q83YLO3O (https://precisio
reaction. It is catalyzed by the pyruvate dehydrogenase
complex. Other conversions between pyruvate and acetyl-CoA n.fda.gov/uniisearch/srs/unii/7
are possible. For example, pyruvate formate lyase 6Q83YLO3O)
disproportionates pyruvate into acetyl-CoA and formic acid. CompTox DTXSID30992686 (https://com
Dashboard (EPA) ptox.epa.gov/dashboard/chem
At low glucose levels, the production of acetyl-CoA is linked to
β-oxidation of fatty acids. Fatty acids are first converted to acyl- ical/details/DTXSID30992686)
CoA. Acyl-CoA is then degraded in a four-step cycle of InChI
oxidation, hydration, oxidation and thiolysis catalyzed by four
respective enzymes, namely acyl-CoA dehydrogenase, enoyl- InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14
CoA hydratase, 3-hydroxyacyl-CoA dehydrogenase, and (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(4

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11/8/24, 7:46 AM Acetyl-CoA - Wikipedia
thiolase. The cycle produces a new fatty acid chain with two 5-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-
fewer carbons and acetyl-CoA as a byproduct.[15] 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
Functions Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N

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(4
Intermediates in various pathways 5-13)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,
In cellular respiration 26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,
Citric acid cycle: 38)/t13-,16-,17-,18+,22-/m1/s1
Key: ZSLZBFCDCINBPY-ZSJPKINUBJ
Through a series of chemical reactions, stored energy is
released through the oxidation of acetyl-CoA derived from SMILES
carbohydrates, fats, and proteins into adenosine O=C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP
triphosphate (ATP) and carbon dioxide. (=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1
Fatty acid metabolism c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O)C
CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)CO
Acetyl-CoA is produced by the breakdown of both
P(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]
carbohydrates (by glycolysis) and lipids (by β-oxidation). It ([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)
then enters the citric acid cycle in the mitochondrion by O
combining with oxaloacetate to form citrate.[16][17]
Properties
Two acetyl-CoA molecules condense to form acetoacetyl-
CoA, which gives rise to the formation of acetoacetate and Chemical formula C23H38N7O17P3S
[16] Acetoacetate, β-hydroxybutyrate, 809.57 g·mol−1
β-hydroxybutyrate. Molar mass
and their spontaneous breakdown product acetone[18] are UV-vis (λmax) 260 nm; 232 nm[1]
frequently, but confusingly, known as ketone bodies (as
Absorbance ε260 = 16.4 mM−1 cm−1
they are not "bodies" at all, but water-soluble chemical
substances). The ketone bodies are released by the liver (adenosine)[1]
into the blood. All cells with mitochondria can take ketone ε232 = 8.7 mM−1 cm−1
bodies up from the blood and reconvert them into acetyl- (thioester)[1]
CoA, which can then be used as fuel in their citric acid Δε232 on thioester hydrolysis =
cycles, as no other tissue can divert its oxaloacetate into −4.5 mM−1 cm−1[1]
the gluconeogenic pathway in the way that the liver does.
Unlike free fatty acids, ketone bodies can cross the blood– Except where otherwise noted, data are given for
brain barrier and are therefore available as fuel for the cells materials in their standard state (at 25 °C [77 °F],
100 kPa).
of the central nervous system, acting as a substitute for
glucose, on which these cells normally survive.[16] The verify (what is ?)
occurrence of high levels of ketone bodies in the blood Infobox references
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 insulin concentration in the blood
is high, and that of glucagon is low (i.e. after meals), the acetyl-
CoA produced by glycolysis condenses as normal with
oxaloacetate to form citrate in the mitochondrion. However,
instead of continuing through the citric acid cycle to be
converted to carbon dioxide and water, the citrate is removed
from the mitochondrion into the cytoplasm.[16] There it is
cleaved by ATP citrate lyase into acetyl-CoA and oxaloacetate.
The oxaloacetate is returned to the mitochondrion as malate β-Oxidation of fatty acids
(and then converted back into oxaloacetate to transfer more
acetyl-CoA out of the mitochondrion).[19] This cytosolic acetyl-
CoA can then be used to synthesize fatty acids through carboxylation by acetyl-CoA carboxylase into
malonyl CoA, the first committed step in the synthesis of fatty acids.[19][20] This conversion occurs primarily
in the liver, adipose tissue and lactating mammary glands, where the fatty acids are combined with glycerol
to form triglycerides, the major fuel reservoir of most animals. Fatty acids are also components of the
phospholipids that make up the bulk of the lipid bilayers of all cellular membranes.[16]
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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 cytosolic acetyl-CoA can also condense with acetoacetyl-CoA to form 3-hydroxy-3-methylglutaryl-CoA
(HMG-CoA) which is the rate-limiting step controlling the synthesis of cholesterol.[16] Cholesterol can be
used as is, as a structural component of cellular membranes, or it can be used to synthesize steroid
hormones, bile salts, and vitamin D.[16][20]
Acetyl-CoA can be carboxylated in the cytosol by acetyl-CoA carboxylase, giving rise to malonyl-CoA, a
substrate required for synthesis of flavonoids and related polyketides, for elongation of fatty acids to
produce waxes, cuticle, and seed oils in members of the Brassica family, and for malonation of proteins and
other phytochemicals.[21] 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 lysine residues of histone and
nonhistone proteins in the posttranslational modification acetylation. This acetylation is catalyzed by
acetyltransferases. This acetylation affects cell growth, mitosis, and apoptosis.[22]
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.[23]
Acetyl-CoA is also an allosteric activator of pyruvate carboxylase.[24]

Interactive pathway map

Click on genes, proteins and metabolites below to visit Gene Wiki pages and related Wikipedia articles. The
pathway can be downloaded and edited at WikiPathways (http://www.wikipathways.org).

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[
]
]

TCACycle_WP78 edit (http://www.wikipathways.org/index.php/ Statin pathway edit (http://www.wikipathways.org/index.php/Pa

Pathway:WP78) thway:WP430)

See also
Malonyl-CoA decarboxylase

References
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709). ISSN 0264-6021 (https://search.worldcat.org/issn/0264-6021). PMC 2859305 (https://www.ncbi.nlm.nih.g
ov/pmc/articles/PMC2859305). PMID 18613815 (https://pubmed.ncbi.nlm.nih.gov/18613815).

https://en.wikipedia.org/wiki/Acetyl-CoA 6/7
11/8/24, 7:46 AM Acetyl-CoA - Wikipedia

External links
Acetyl+Coenzyme+A (https://meshb.nlm.nih.gov/record/ui?name=Acetyl+Coenzyme+A) at the U.S. National
Library of Medicine Medical Subject Headings (MeSH)

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