2-Hydroxyisobutyric acid is the
organic compound with the formula . A white solid, it is classified as an
hydroxycarboxylic acid. It has been considered as a naturally occurring precursor to
polyester
Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...
s. It is closely related to
lactic acid ().
Occurrences
The enzyme 2-hydroxyisobutyryl coenzyme A (CoA)
mutase
A mutase is an enzyme of the isomerase class that catalyzes the movement of a functional group from one position to another within the same molecule. In other words, mutases catalyze intramolecular group transfers. Examples of mutases include ''bis ...
isomerizes 3-hydroxybutyryl coenzyme A into 2-hydroxyisobutyryl coenzyme A. Hydrolysis of the latter gives 2-hydroxyisobutyric acid.
The
amides formed from this carboxylic acid and the ε-amino group of
lysine
Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −C ...
residues are a kind of
post translational modification.
Ethyl methacrylate (an industrially important
monomer methacrylic acid) was first obtained by treating the ethyl ester of 2-hydroxyisobutyric acid with
phosphorus pentachloride in an apparent dehydration reaction.
References
Alpha hydroxy acids
{{alcohol-stub