Propane-1,2,3-tricarboxylic acid

Propane-1,2,3-tricarboxylic acid
Names

IUPAC name Propane-1,2,3-tricarboxylic acid
Other names Tricarballylic acid, carballylic acid, 1,2,3-propanetricarboxylic acid, beta-carboxyglutaric acid
Identifiers
CAS Number	99-14-9^Y
ChemSpider	14220^N
Jmol interactive 3D	Image
PubChem	14925
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	176.12 g/mol
Appearance	colourless solid
Melting point	156-161
Solubility in water	sl. in water
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

Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. 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 fumonisin B1 and B2 and AAL toxin T_A and in macrocyclic inhibitors of Ras farnesyl-protein transferase (FPTase) like actinoplanic acid.

It can be synthesized in two steps from fumaric acid.^[2]

Mechanism of the inhibition of Aconitase

Aconitase normally catalyses, via Aconitic acid, the interconversion of citric acid into isocitric acid (see figure above). Propane-1,2,3-tricarboxylic acid is very suited to bind to aconitase as it only lacks the hydroxide group compourd to citric acid. On the other hand, as the hydroxide group is essential to proceed from citric acid to aconitic acid, the enzyme is not able to complete the reaction. The enzyme is stuck with a molecule it cannot get rid of.

References

↑ Russell, J. B., and N. Forsberg. 1986. Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism. British Journal of Nutrition (1986), 56:153-162 56:153-162. doi:10.1079/BJN19860095
↑ H. T. Clarke and T. F. Murray (1941). "Tricarballylic Acid". Org. Synth. ; Coll. Vol. 1, p. 523

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