Propane-1,2,3-tricarboxylic acid: Difference between revisions
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'''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 group]]s. The compound is an inhibitor of the enzyme [[aconitase]] and |
'''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 group]]s. The compound is an inhibitor of the enzyme [[aconitase]] and therefore interferes with the [[Krebs cycle]].<ref>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}}</ref> |
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[[Ester]]s of propane-1,2,3-tricarboxylic acid are found in [[natural product]]s such as the [[mycotoxin]]s [[fumonisin]] B1 and B2 and [[AAL toxin TA|AAL toxin T<sub>A</sub>]] and in macrocyclic inhibitors of [[Ras farnesyl-protein transferase]] (FPTase) like [[actinoplanic acid]]. |
[[Ester]]s of propane-1,2,3-tricarboxylic acid are found in [[natural product]]s such as the [[mycotoxin]]s [[fumonisin]] B1 and B2 and [[AAL toxin TA|AAL toxin T<sub>A</sub>]] and in macrocyclic inhibitors of [[Ras farnesyl-protein transferase]] (FPTase) like [[actinoplanic acid]]. |
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Revision as of 11:51, 18 September 2011
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| Names | |
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| IUPAC name
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 | |
3D model (JSmol)
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| ECHA InfoCard | 100.002.485 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H8O6 | |
| Molar mass | 176.12 g/mol |
| Appearance | colourless solid |
| Melting point | 156-161 |
| sl. in water | |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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 molucule 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". Organic Syntheses; Collected Volumes, vol. 1, p. 523.