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Α-Ketoisovaleric acid

α-Ketoisovaleric acid is an organic compound with the formula (CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub>H. 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, (CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub><sup>−</sup>.

Synthesis and reactions

α-Ketoisovalerate undergoes hydroxymethylation to give ketopantoate:

(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 isobutyraldehyde:

(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 biofuel isobutanol by reduction of isobutyraldehyde obtained from ketoisovalerate.

See also

References