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Oxalosuccinic acid

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Oxalosuccinic acid
Names
Preferred IUPAC name 1-Oxopropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.230.021 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: UFSCUAXLTRFIDC-UHFFFAOYSA-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
SMILES
  • C(C(C(=O)C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula C6H6O7
Molar mass 190.108
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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.

References

  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.
Citric acid cycle metabolic pathway

Acetyl-CoA

+ H2O

Oxaloacetate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightNADH +H NAD

Malate

Leftward reaction arrow with minor substrate(s) from bottom right  H2O

Fumarate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightFADH2 FAD

Succinate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightCoA + ATP (GTP) Pi + ADP (GDP)

Succinyl-CoA

NADH + H + CO2
CoA NAD

Citrate

  H2O Rightward reaction arrow with minor product(s) to top right

cis-Aconitate

H2O   Rightward reaction arrow with minor substrate(s) from top left

Isocitrate

NAD(P) NAD(P)H +  H Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

Oxalosuccinate

  CO2 Rightward reaction arrow with minor product(s) to top right

2-oxoglutarate

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