Propane-1,2,3-tricarboxylic acid: Difference between revisions

| verifiedrevid = 443610281

| ImageFile=CarballylicA.png

| ImageSize=300px

| IUPACName= Propane-1,2,3-tricarboxylic acid

| OtherNames= Tricarballylic acid, carballylic acid, 1,2,3-propanetricarboxylic acid, ''beta''-carboxyglutaric acid

| Section1= {{Chembox Identifiers

| CASNo=99-14-9

| PubChem=14925

| SMILES=C(C(CC(=O)O)C(=O)O)C(=O)O

| Section2= {{Chembox Properties

| Formula=C₆H₈O₆

| MolarMass=176.12 g/mol

| Appearance= colourless solid

| Density=

| MeltingPt=156-161

| BoilingPt=

| Solubility=sl. in water

| Section3= {{Chembox Hazards

| MainHazards=

| FlashPt=

| Autoignition=

| Section8 = {{Chembox Related

| OtherCpds = [[citric acid]]

}}

'''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>

[[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_A]] and in macrocyclic inhibitors of [[Ras farnesyl-protein transferase]] (FPTase) like [[actinoplanic acid]].

It can be synthesized in two steps from [[fumaric acid]].<ref>{{OrgSynth | author = H. T. Clarke and T. F. Murray | title = Tricarballylic Acid | collvol = 1 | collvolpages = 523| year = 1941 | prep = CV1P0523}}</ref>

== Mechanism of the inhibition of Aconitase ==

<gallery>

Image:Citrate wpmp.png|<center>[[Citric acid]]</center>

Image:Cis-Aconitate wpmp.png|<center>[[Aconitic acid]]</center>

Image:Threo-Ds-isocitrate wpmp.png|<center>[[Isocitric acid]]</center>

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.

[[Category:Lyase inhibitors]]

[[fr:Acide tricarballylique]]