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Α-Ketoisovaleric acid

Chemical compound From Wikipedia, the free encyclopedia

Α-Ketoisovaleric acid
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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]

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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]

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See also

References

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