Propane-1,2,3-tricarboxylic acid

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]

Propane-1,2,3-tricarboxylic acid
Names
Preferred IUPAC name
Propane-1,2,3-tricarboxylic acid
Other names
  • Tricarballylic acid
  • Carballylic acid
  • 3-carboxypentane–1,5-dioic acid
  • 1,2,3-Propanetricarboxylic acid
  • β-Carboxyglutaric acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.485
PubChem CID
UNII
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) N
    Key: KQTIIICEAUMSDG-UHFFFAOYSA-N 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).
N verify (what is YN ?)
Infobox references

Esters of propane-1,2,3-tricarboxylic acid are found in natural products such as the mycotoxins fumonisins B1 and B2 and AAL toxin TA, 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

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
  1. Russell, James B.; Forsberg, Neil (1986). "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, vol. 1, p. 523
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