Oxalosuccinic acid

Oxalosuccinic acid
Names
	Preferred IUPAC name 1-Oxopropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number	1948-82-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7815 ;
ChemSpider	947 ;
ECHA InfoCard	100.230.021
KEGG	C05379 ;
PubChem CID	972;
UNII	DFK99PW32K ;
CompTox Dashboard (EPA)	DTXSID30862799 ;
	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 [77 °F], 100 kPa). verify (what is ?) 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

^ 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.
^ 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.

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[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.

[1]

[2]

Names

Preferred IUPAC name 1-Oxopropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number	1948-82-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:7815^N
ChemSpider	947^N
ECHA InfoCard	100.230.021
KEGG	C05379^N
PubChem CID	972
UNII	DFK99PW32K^Y
CompTox Dashboard (EPA)	DTXSID30862799
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
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Oxalosuccinic acid

References

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