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Keto acid

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(Redirected fromΒ-keto acid)

Organic compounds with a –COOH group and a C=O group

Not to be confused withoxyacid.

Pyruvic acid (top),acetoacetic acid andlevulinic acid (bottom)

Inorganic chemistry,keto acids orketoacids (also calledoxo carboxylic acids)^[1] areorganic compounds that contain acarboxylic acid group (−COOH) and aketone group (>C=O).^[2] In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in theKrebs citric acid cycle and inglycolysis.^[3]

Common types of keto acids include:

Alpha-keto acids, alpha-ketoacids, or2-oxoacids have the keto group adjacent to the carboxylic acid. They often arise byoxidative deamination ofamino acids, and reciprocally, they areprecursors to the same. Alpha-keto acids possesses extensive chemistry asacylation agents.^[4] Furthermore, alpha-keto acids such asphenylpyruvic acid are endogenous sources forcarbon monoxide (as agasotransmitter) and pharmaceuticalprodrug scaffold.^[5] Important representatives:
- pyruvic acid, pervasive intermediate in metabolism.
- oxaloacetic acid, a component of theKrebs cycle.^[6]
- alpha-ketoglutaric acid, a 5-carbon ketoacid derived fromglutamic acid. Alpha-ketoglutarate participates incell signaling by functioning as acoenzyme.^[7] It is commonly used intransamination reactions.
Beta-keto acids, beta-ketoacids, or 3-oxoacids, such asacetoacetic acid, have the ketone group at the second carbon from the carboxylic acid. They generally form by theClaisen condensation. The presence of the keto group at the beta position allows them to easily undergo thermaldecarboxylation.^[8]
Gamma-keto acids, Gamma-ketoacids, or 4-oxoacids have the ketone group at the third carbon from the carboxylic acid.Levulinic acid is an example.

Keto acids appear in a wide variety of anabolic pathways in metabolism. For instance, in plants (specifically, inhemlock,pitcher plants, andfool's parsley), 5-oxo-octanoic acid is converted in enzymatic and non-enzymatic steps into thecyclic class ofconiine alkaloids.^[9]

When ingestedsugars andcarbohydrate levels are low, stored fats and proteins are the primary source of energy production.Glucogenic amino acids from proteins and/orGlycerol fromTriglycerides are converted toglucose.Ketogenic amino acids can be deaminated to produce alpha keto acids andketone bodies.

Alpha keto acids are used primarily as energy for liver cells and infatty acid synthesis, also in the liver.

References

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^IUPAC,Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "oxo carboxylic acids".doi:10.1351/goldbook.O04376
^Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a18_313
^Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000.ISBN 1-57259-153-6.
^Penteado, Filipe; Lopes, Eric F.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.; Lenardão, Eder J. (16 April 2019). "α-Keto Acids: Acylating Agents in Organic Synthesis".Chemical Reviews.119 (12):7113–7278.doi:10.1021/acs.chemrev.8b00782.PMID 30990680.S2CID 119535331.
^Hopper, Christopher P.; De La Cruz, Ladie Kimberly; Lyles, Kristin V.; Wareham, Lauren K.; Gilbert, Jack A.; Eichenbaum, Zehava; Magierowski, Marcin; Poole, Robert K.; Wollborn, Jakob; Wang, Binghe (2020-12-23)."Role of Carbon Monoxide in Host–Gut Microbiome Communication".Chemical Reviews.120 (24):13273–13311.doi:10.1021/acs.chemrev.0c00586.ISSN 0009-2665.PMID 33089988.S2CID 224824871.
^Kerber, Robert C.; Fernando, Marian S. (October 2010). "α-Oxocarboxylic Acids".Journal of Chemical Education.87 (10):1079–1084.doi:10.1021/ed1003096.
^Hewitson, K.S.; McNeill, L.A.; Elkins, J.M.; Schofield, C.J. (1 June 2003). "The role of iron and 2-oxoglutarate oxygenases in signalling".Biochemical Society Transactions.31 (3):510–515.doi:10.1042/bst0310510.PMID 12773146.
^Smith, Michael B. (2017),"Functional Group Exchange Reactions",Organic Synthesis, Elsevier, p. 137,doi:10.1016/b978-0-12-800720-4.00003-9,ISBN 978-0-12-800720-4, retrieved2022-06-01
^Leete, E.; Olson, J. O. (1970)."5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine".Journal of the Chemical Society D: Chemical Communications (23):1651–1652.doi:10.1039/C29700001651.ISSN 0577-6171.