Propane-1,2,3-tricarboxylic acid

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Propane-1,2,3-tricarboxylic acid
Propane-1,2,3-tricarboxylic acid-2D-by-AHRLS-2012.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.485
Properties
C6H8O6
Molar mass 176.12 g·mol−1
Melting point 156-161
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 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[edit]

Aconitase normally catalyses, via the intermediate aconitic acid, the interconversion of citric acid into isocitric acid (see figure above). 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[edit]

  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". Org. Synth. ; Coll. Vol., 1, p. 523