Oxalosuccinic acid

Oxalosuccinic acid
Names
Preferred IUPAC name
1-Oxopropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number
  • 1948-82-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:7815 ☒N
ChemSpider
  • 947 ☒N
ECHA InfoCard 100.230.021 Edit this at Wikidata
KEGG
  • C05379 ☒N
PubChem CID
  • 972
UNII
  • DFK99PW32K checkY
CompTox Dashboard (EPA)
  • DTXSID30862799 Edit this at Wikidata
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) ☒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
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
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.[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

  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.
  • v
  • t
  • e
+ H2O
Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right
NADH +H+
NAD+
Leftward reaction arrow with minor substrate(s) from bottom right
 
H2O
Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right
FADH2
FAD
Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom right
CoA + ATP (GTP)
Pi + ADP (GDP)
NADH + H+ + CO2
CoA NAD+
 
H2O
Rightward reaction arrow with minor product(s) to top right

cis-Aconitate

H2O
 
Rightward reaction arrow with minor substrate(s) from top left
NAD(P)+
NAD(P)H +  H+
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
CO2
Rightward reaction arrow with minor product(s) to top right
Stub icon

This biochemistry article is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e