Oxalosuccinic acid

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Oxalosuccinic acid
Oxalbernsteinsäure.png
Names
Preferred IUPAC name
1-Oxopropane-1,2,3-tricarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.230.021 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13) ☒N
    Key: UFSCUAXLTRFIDC-UHFFFAOYSA-N ☒N
  • InChI=1/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)
    Key: UFSCUAXLTRFIDC-UHFFFAOYAK
  • C(C(C(=O)C(=O)O)C(=O)O)C(=O)O
Properties
C6H6O7
Molar mass 190.108
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Oxalosuccinic acid is a substrate of the citric acid cycle. It is acted upon by isocitrate dehydrogenase. Salts and esters of oxalosuccinic acid are known as oxalosuccinates.

Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. It's a keto acid, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Isocitrate is first oxidized by coenzyme NAD+ to form oxalosuccinic acid/oxalosuccinate.[1] Oxalosuccinic acid is both an alpha-keto and a beta-keto acid (an unstable compound) and it is the beta-ketoic property that allows the loss of carbon dioxide in the enzymatic reaction in conversion to the five-carbon molecule 2-oxoglutarate.[2]

References[edit]

  1. ^ Ochoa S (May 1948). "Biosynthesis of tricarboxylic acids by carbon dioxide fixation; the preparation and properties of oxalosuccinic acid". The Journal of Biological Chemistry. 174 (1): 115–22. doi:10.1016/S0021-9258(18)57381-6. PMID 18914069.
  2. ^ Romkina AY, Kiriukhin MY (2017-04-19). "Biochemical and molecular characterization of the isocitrate dehydrogenase with dual coenzyme specificity from the obligate methylotroph Methylobacillus Flagellatus". PLOS ONE. 12 (4): e0176056. Bibcode:2017PLoSO..1276056R. doi:10.1371/journal.pone.0176056. PMC 5397045. PMID 28423051.