α-Ketoisovaleric acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula (CH₃)₂CHC(O)CO₂H. It is a

ketoacid In organic chemistry, keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group () and a ketone group ().Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's En ...

. 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 Valine (symbol Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α- carboxylic acid group (which is in the deprotonat ...

and a precursor to

pantothenic acid Pantothenic acid, also called vitamin B5 is a water-soluble B vitamin and therefore an essential nutrient. All animals require pantothenic acid in order to synthesize coenzyme A (CoA) – essential for fatty acid metabolism – as well as to, i ...

, a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base ketoisovalerate, (CH₃)₂CHC(O)CO₂⁻.

Synthesis and reactions

α-Ketoisovalerate undergoes

hydroxymethylation Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes. Hydroxymethylation with formaldehyde A common method for hydroxym ...

to give

ketopantoate Ketopantoic acid is the organic compound with the formula HOCH2(CH3)2CC(O)CO2H. At physiological conditions, ketopantoic acid exists as its conjugate base, ketopantoate (HOCH2(CH3)2CC(O)CO2−). Biosynthetic context Its biosynthesis proceeds from ...

: :(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 Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as ...

: :(CH₃)₂CHC(O)CO₂H → (CH₃)₂CHCHO + CO₂ Genetic engineering has been used to produce the

biofuel Biofuel is a fuel that is produced over a short time span from biomass, rather than by the very slow natural processes involved in the formation of fossil fuels, such as oil. According to the United States Energy Information Administration (E ...

isobutanol Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as ''i''-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either dire ...

by reduction of isobutyraldehyde obtained from ketoisovalerate.

References

Alpha-keto acids {{biochem-stub

Synthesis and reactions

See also

References