| Propane-1,2,3-tricarboxylic acid | |
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Propane-1,2,3-tricarboxylic acid |
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Other names
Tricarballylic acid, carballylic acid, 1,2,3-propanetricarboxylic acid, beta-carboxyglutaric acid |
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| Identifiers | |
| CAS number | 99-14-9 |
| PubChem | 14925 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular 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 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 TA and in macrocyclic inhibitors of Ras farnesyl-protein transferase (FPTase) like actinoplanic acid.
It can be synthesized in two steps from fumaric acid.[2]
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 molucule it cannot get rid of.