| Revision as of 12:02, 18 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation← Previous edit |
Latest revision as of 18:03, 27 February 2024 edit undoAndrew Murkin (talk | contribs)69 editsm The OH group is called hydroxyl. Hydroxide is the anion.Tag: Visual edit |
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| verifiedrevid = 443610281 |
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| ImageFile=CarballylicA.png |
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|verifiedrevid = 451131660 |
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| ImageSize=300px |
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| IUPACName= Propane-1,2,3-tricarboxylic acid |
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|ImageFile=Propane-1,2,3-tricarboxylic acid-2D-by-AHRLS-2012.png |
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|ImageSize=200px |
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| OtherNames= Tricarballylic acid, carballylic acid, 1,2,3-propanetricarboxylic acid, ''beta''-carboxyglutaric acid |
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|PIN= Propane-1,2,3-tricarboxylic acid |
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| Section1= {{Chembox Identifiers |
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|OtherNames= {{bulletedlist|Tricarballylic acid|Carballylic acid|3-carboxypentane–1,5-dioic acid|1,2,3-Propanetricarboxylic acid|β-Carboxyglutaric acid}} |
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| CASNo=99-14-9 |
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|Section1={{Chembox Identifiers |
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| PubChem=14925 |
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|CASNo_Ref = {{cascite|correct|??}} |
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| SMILES=C(C(CC(=O)O)C(=O)O)C(=O)O |
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|CASNo=99-14-9 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = RA5QH2J020 |
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|PubChem=14925 |
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|SMILES=C(C(CC(=O)O)C(=O)O)C(=O)O |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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|ChemSpiderID = 14220 |
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|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) |
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|InChIKey = KQTIIICEAUMSDG-UHFFFAOYAL |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChI = 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) |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = KQTIIICEAUMSDG-UHFFFAOYSA-N |
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| Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=6|H=8|O=6 |
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| Formula=C<sub>6</sub>H<sub>8</sub>O<sub>6</sub> |
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|MeltingPt=156-161 |
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| MolarMass=176.12 g/mol |
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|Solubility=Soluble |
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| Appearance= colourless solid |
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| Density= |
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| MeltingPt=156-161 |
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| Solubility=sl. in water |
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| Section3= {{Chembox Hazards |
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|OtherCompounds = ] |
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'''Propane-1,2,3-tricarboxylic acid''', also known as '''tricarballylic acid''', '''carballylic acid''', and '''''beta''-carboxyglutaric acid''', is a ] that has three ] ]s. The compound is an inhibitor of the enzyme ] and therefore interferes with the ].<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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'''Propane-1,2,3-tricarboxylic acid''', also known as '''tricarballylic acid''', '''carballylic acid''', and '''β-carboxyglutaric acid''', is a ]. The compound is an inhibitor of the enzyme ] and therefore interferes with the ].<ref>{{Cite journal | doi = 10.1079/BJN19860095| pmid = 3676191| title = Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism| journal = British Journal of Nutrition| volume = 56| issue = 1| pages = 153–62| year = 1986| last1 = Russell| first1 = James B.| last2 = Forsberg| first2 = Neil| doi-access = free}}</ref> |
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]s of propane-1,2,3-tricarboxylic acid are found in ]s such as the ]s ] B1 and B2 and ] and in macrocyclic inhibitors of ] (FPTase) like ]. |
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]s of propane-1,2,3-tricarboxylic acid are found in ]s such as the ]s ]s ] and ] and ], and in macrocyclic inhibitors of ] (FPTase) such as ]. |
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It can be synthesized in two steps from ].<ref>{{OrgSynth | author = H. T. Clarke and T. F. Murray | title = Tricarballylic Acid | collvol = 1 | collvolpages = 523| year = 1941 | prep = CV1P0523}}</ref> |
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Propane-1,2,3-tricarboxylic acid can be synthesized in two steps from ].<ref>{{OrgSynth |author1 = H. T. Clarke |author2 =T. F. Murray | title = Tricarballylic Acid | collvol = 1 | collvolpages = 523| year = 1941 | prep = CV1P0523}}</ref> |
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== Mechanism of the inhibition of Aconitase == |
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== Mechanism of the inhibition of aconitase == |
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<gallery> |
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<gallery widths="110" heights="170"> |
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Image:Citrate wpmp.png|<center>]</center> |
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Image:Citrate wpmp.png|{{center|]}} |
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Image:Cis-Aconitate wpmp.png|<center>]</center> |
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Image:Cis-Aconitate wpmp.png|{{center|]}} |
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Image:Threo-Ds-isocitrate wpmp.png|<center>]</center> |
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Image:isocitric acid.svg|{{center|]}} |
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</gallery> |
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</gallery> |
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Aconitase normally catalyses, via ], the interconversion of ] into ] (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. |
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Aconitase normally catalyses, via the intermediate ], the interconversion of ] into ]. Propane-1,2,3-tricarboxylic acid is well suited to bind to aconitase as it only lacks the hydroxyl group in comparison to citric acid. However, the hydroxyl 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. |
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== References == |
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== References == |
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