α-Ketoisovaleric acid

α-Ketoisovaleric acid is an organic compound with the formula (CH3)2CHC(O)CO2H. It is a ketoacid. 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 valine and a precursor to pantothenic acid, a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base ketoisovalerate, (CH3)2CHC(O)CO2−.[1]

α-Ketoisovaleric acid
Names
Preferred IUPAC name
3-Methyl-2-oxobutanoic acid
Other names
2-Ketoisovaleric acid; α-Ketovaline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.969
KEGG
UNII
  • InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) checkY
    Key: QHKABHOOEWYVLI-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
    Key: QHKABHOOEWYVLI-UHFFFAOYAY
  • O=C(C(=O)O)C(C)C
Properties
C5H8O3
Molar mass 116.116 g·mol−1
Appearance colorless or white solid or oil
Melting point 31.5 °C (88.7 °F; 304.6 K)
Boiling point 170.5 °C (338.9 °F; 443.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Synthesis and reactions

α-Ketoisovalerate undergoes hydroxymethylation to give ketopantoate:[1]

(CH3)2CHC(O)CO2− + CH2O → HOCH2(CH3)2CC(O)CO2−

This conversion is catalyzed by ketopantoate hydroxymethyltransferase.

Like many α-ketoacids, α-ketoisovaleric acid is prone to decarboxylation to give isobutyraldehyde:

(CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2

Genetic engineering has been used to produce the biofuel isobutanol by reduction of isobutyraldehyde obtained from ketoisovalerate.[2]

See also

References
  1. Leonardi, Roberta; Jackowski, Suzanne (April 2007). "Biosynthesis of Pantothenic Acid and Coenzyme A". EcoSal Plus. 2 (2). doi:10.1128/ecosalplus.3.6.3.4. ISSN 2324-6200. PMC 4950986. PMID 26443589.
  2. Atsumi, Shota; Hanai, Taizo; Liao, James C. (2008). "Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.


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