Acetoacetyl-CoA
Names | |
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IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl dihydrogen diphosphate]
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Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.014.378 |
IUPHAR/BPS |
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MeSH | acetoacetyl+CoA |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C25H40N7O18P3S | |
Molar mass | 851.61 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acetoacetyl CoA is the precursor of
It is created from
Additionally, it reacts with NADPH-dependent acetoacetyl-coenzyme A reductase, also known as PhaB, in a pathway that produces polyester polyhydroxyalkanoate (PHA). The reduction of acetoacetyl-coA by Pha creates (R)-3-hydroxybutyryl-CoA, which polymerizes to PHA.[4] The pathway is present in bacteria such as Ralstonia eutropha and the PCC6803 strain of Synechocystis.[5] Mover over, Acetoacetyl-CoA is involved with neuronal development involving lipogenesis and providing fats and cholesterol for neuronal cells.
Mutations
Mitochondrial
Mutations in mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase (HMG-CoA synthase) is another inherited autosomal recessive disorder affecting the catabolism of ketone bodies and can lead to the build-up of acetoacetyl-CoA.[7]
Additional application
Acetoacetyl-CoA also behaves as a product of acetoacetyl-CoA synthetase (AACS) within the cytosol, using acetoacetate as the substrate, the reaction provides acetyl groups for lipogenesis.[8] Understanding acetoacetyl-CoA is important in cholesterol development and lipogenesis and Acetoacetyl-CoA synthetase playing a role in its development, it also plays a significant role within the brain. Cholesterol and fats have been observed in high concentrations within neuronal tissue, as well as high AACS mRNA expression levels within cells of the hippocampus and cortical region. In addition, they play a significant role in neuronal development during the early embryonic and fetal developmental stages.[9]
See also
- Mevalonate pathway
- Acetoacetic acid
- Beta-hydroxybutyryl-CoA dehydrogenase
References
- ^ PMID 22985732.
- OCLC 974910578.
- PMID 27372278.
- PMID 23913421.
- PMID 11010896.
- ^ Bissonnette, Bruno; Luginbuehl, Igor; Marciniak, Bruno; Dalens, Bernard J. (2006), "Mitochondrial Acetoacetyl-CoA Thiolase (ACAT) Deficiency", Syndromes: Rapid Recognition and Perioperative Implications, New York, NY: The McGraw-Hill Companies, retrieved 2022-12-08
- S2CID 24115345.
- PMID 23123469.
- PMID 23000407.