Propane-1,2,3-tricarboxylic acid

Propane-1,2,3-tricarboxylic acid
Names
	IUPAC name Propane-1,2,3-tricarboxylic acid Or 3-carboxypentane–1,5-dioic acid
	Other names Tricarballylic acid; Carballylic acid; 1,2,3-Propanetricarboxylic acid; β-Carboxyglutaric acid;
Identifiers
CAS Number	99-14-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	14220 ;
ECHA InfoCard	100.002.485
PubChem CID	14925;
CompTox Dashboard (EPA)	DTXSID8059186 ;
	InChI InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12) Key: KQTIIICEAUMSDG-UHFFFAOYSA-N ; InChI=1/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12) Key: KQTIIICEAUMSDG-UHFFFAOYAL;
	SMILES C(C(CC(=O)O)C(=O)O)C(=O)O;
Properties
Chemical formula	C6H8O6
Molar mass	176.124 g·mol−1
Melting point	156-161
Solubility in water	Soluble
Related compounds
Related compounds	citric acid
	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

Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and β-carboxyglutaric acid, is a tricarboxylic acid. The compound is an inhibitor of the enzyme aconitase and therefore interferes with the Krebs cycle.[1]

Esters of propane-1,2,3-tricarboxylic acid are found in natural products such as the mycotoxins fumonisins B1 and B2 and AAL toxin T_A, and in macrocyclic inhibitors of Ras farnesyl-protein transferase (FPTase) such as actinoplanic acid.

Propane-1,2,3-tricarboxylic acid can be synthesized in two steps from fumaric acid.[2]

Mechanism of the inhibition of aconitase

Citric acid
Aconitic acid
Isocitric acid

Aconitase normally catalyses, via the intermediate aconitic acid, the interconversion of citric acid into isocitric acid. Propane-1,2,3-tricarboxylic acid is well suited to bind to aconitase as it only lacks the hydroxide group in comparison to citric acid. However, the hydroxide group is essential to proceed from citric acid to aconitic acid, therefore the enzyme is not able to complete the reaction with propane-1,2,3-tricarboxylic acid.

References

Russell, James B.; Forsberg, Neil (2007). "Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism". British Journal of Nutrition. 56 (1): 153–62. doi:10.1079/BJN19860095. PMID 3676191.
H. T. Clarke; T. F. Murray (1941). "Tricarballylic Acid". Organic Syntheses.; Collective Volume, 1, p. 523

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[1] Russell, James B.; Forsberg, Neil (2007). "Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism". British Journal of Nutrition. 56 (1): 153–62. doi:10.1079/BJN19860095. PMID 3676191.

[2] H. T. Clarke; T. F. Murray (1941). "Tricarballylic Acid". Organic Syntheses.; Collective Volume, 1, p. 523