Chemistry:Keto acid

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Short description: Organic compounds with a –COOH group and a C=O group


Pyruvic acid (top), acetoacetic acid and levulinic acid (bottom)

In organic chemistry, keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group (–COOH) and a ketone group (>C=O).[1] In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in the Krebs citric acid cycle and in glycolysis.[2]

Common types of keto acids include:

Keto acids appear in a wide variety of anabolic pathways in metabolism. For instance, in plants (specifically, in hemlock, pitcher plants, and fool's parsley), 5-oxo-octanoic acid is converted in enzymatic and non-enzymatic steps into the cyclic class of coniine alkaloids.[8]

When ingested sugars and carbohydrate levels are low, stored fats and proteins are the primary source of energy production. Glucogenic amino acids from proteins and/or Glycerol from Triglycerides are converted to glucose. Ketogenic amino acids can be deaminated to produce alpha keto acids and ketone bodies.

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

See also

References

  1. Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18_313
  2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN:1-57259-153-6.
  3. 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. 
  4. Hopper, Christopher P.; De La Cruz, Ladie Kimberly; Lyles, Kristin V.; Wareham, Lauren K.; Gilbert, Jack A.; Eichenbaum, Zehava; Magierowski, Marcin; Poole, Robert K. et al. (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. https://doi.org/10.1021/acs.chemrev.0c00586. 
  5. Kerber, Robert C.; Fernando, Marian S. (October 2010). "α-Oxocarboxylic Acids". Journal of Chemical Education 87 (10): 1079–1084. doi:10.1021/ed1003096. 
  6. 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. 
  7. Smith, Michael B. (2017), "Functional Group Exchange Reactions" (in en), Organic Synthesis (Elsevier): pp. 137, doi:10.1016/b978-0-12-800720-4.00003-9, ISBN 978-0-12-800720-4, https://linkinghub.elsevier.com/retrieve/pii/B9780128007204000039, retrieved 2022-06-01 
  8. Leete, E.; Olson, J. O. (1970). "5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine" (in en). Journal of the Chemical Society D: Chemical Communications (23): 1651–1652. doi:10.1039/C29700001651. ISSN 0577-6171. https://pubs.rsc.org/en/content/articlelanding/1970/c2/c29700001651. 

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