| Revision as of 05:31, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 471293612 of page Alpha-Ketoisovaleric_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:20, 10 September 2024 edit Marbletan (talk | contribs)Extended confirmed users5,256 edits no longer a stub |
| Line 1: |
Line 1: |
|
|
{{lowercase title}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 443378375 |
|
| verifiedrevid = 477319257 |
|
|Name=α-Ketoisovaleric acid |
|
| Name=α-Ketoisovaleric acid |
|
|ImageFile=alpha-Ketovaline.svg |
|
| ImageFile=alpha-Ketovaline.svg |
|
|ImageSize= |
|
| ImageSize= |
|
|IUPACName=3-Methyl-2-oxobutanoic acid |
|
| PIN=3-Methyl-2-oxobutanoic acid |
|
|OtherNames=2-Ketoisovaleric acid; α-Ketovaline |
|
| OtherNames=2-Ketoisovaleric acid; α-Ketovaline |
|
|Section1={{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 48 |
|
| ChemSpiderID = 48 |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
| Line 22: |
Line 23: |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo=759-05-7 |
|
| CASNo=759-05-7 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 34P71D50E0 |
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank=DB04074 |
|
| DrugBank=DB04074 |
|
| PubChem=49 |
|
| PubChem=49 |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 16530 |
|
| ChEBI = 16530 |
|
| SMILES = O=C(C(=O)O)C(C)C |
|
| SMILES = O=C(C(=O)O)C(C)C |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=5|H=8|O=3 |
|
| C=5 | H=8 | O=3 |
|
| Appearance= |
|
| Appearance= colorless or white solid or oil |
|
| Density= |
|
| Density= |
|
|
| MeltingPtC= 31.5 |
|
| MeltingPt= |
|
|
|
| BoilingPtC= 170.5 |
|
| BoilingPt= |
|
|
| Solubility= |
|
| Solubility= |
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''α-Ketoisovaleric acid''' is an ] with the formula (CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub>H. It is a ]. With a melting point just above room temperature, it is usually an oil or semi-solid. The compound is colorless. It is a metabolite of ] and a precursor to ], a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base '''ketoisovalerate''', (CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub><sup>−</sup>.<ref name=biosyn>{{Cite journal|last1=Leonardi|first1=Roberta|last2=Jackowski|first2=Suzanne|date=April 2007|title=Biosynthesis of Pantothenic Acid and Coenzyme A|journal=EcoSal Plus|volume=2|issue=2|doi=10.1128/ecosalplus.3.6.3.4|issn=2324-6200|pmc=4950986|pmid=26443589}}</ref> |
|
|
|
|
|
==Synthesis and reactions== |
|
|
α-Ketoisovalerate undergoes ] to give ]:<ref name=biosyn/> |
|
|
:(CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub><sup>−</sup> + CH<sub>2</sub>O → HOCH<sub>2</sub>(CH<sub>3</sub>)<sub>2</sub>CC(O)CO<sub>2</sub><sup>−</sup> |
|
|
This conversion is catalyzed by ketopantoate hydroxymethyltransferase. |
|
|
|
|
|
Like many α-ketoacids, α-ketoisovaleric acid is prone to decarboxylation to give ]: |
|
|
:(CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub>H → (CH<sub>3</sub>)<sub>2</sub>CHCHO + CO<sub>2</sub> |
|
|
Genetic engineering has been used to produce the ] ] by reduction of isobutyraldehyde obtained from ketoisovalerate.<ref>{{cite journal |doi=10.1038/nature06450|title=Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels|year=2008|last1=Atsumi|first1=Shota|last2=Hanai|first2=Taizo|last3=Liao|first3=James C.|journal=Nature|volume=451|issue=7174|pages=86–89|pmid=18172501|bibcode=2008Natur.451...86A|s2cid=4413113}}</ref> |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
|
|
|
==References== |
|
|
<references /> |
|
|
|
|
|
{{Amino acid metabolism intermediates}} |
|
|
|
|
|
{{DEFAULTSORT:Ketoisovaleric acid, alpha-}} |
|
|
] |