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

* 99-14-9 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 14220 N

PubChem CID

* 14925

UNII |

* RA5QH2J020 Y

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

Tracking categories (test):

* SizeSet

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

* 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

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. http://www.orgsyn.org/demo.aspx?prep=CV1P0523. ;  Collective Volume, 1, pp. 523

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*[CID]: Compound ID