2-AMINOISOBUTYRIC ACID, or α-AMINOISOBUTYRIC ACID (AIB) or α-METHYLALANINE or 2-METHYLALANINE, is an amino acid with the structural formula is H2N-C(CH3)2-COOH. It is contained in some antibiotics of fungal origin, e.g. alamethicin and some lantibiotics . It is not one of the proteinogenic amino acids and rather rare in nature (cf. Non-proteinogenic amino acids ). α-Aminoisobutyric acid is a strong helix inducer in peptides . Oligomers of AIB form 310 helices.
In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin , by reaction with ammonia followed by hydrolysis.
* ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959. * ^ Clarke, H. T.; Bean, H. J. (1931). "α-Aminoisobutyric acid". Organic Syntheses . 11: 4. ; Collective Volume, 2, p. 29 .
BAIBA is found as a normal metabolite of skeletal muscle in 2014. The plasma concentrations are increased in human by exercise. The production is likely a result of enhanced mitochondrial activity as the increase is also observed in the muscle of PGC-1a overexpression mice. BAIBA is proposed as protective factor against metabolic disorder since it can induce brown fat function.
Roberts Lee D, Boström P, O Sullivan John F, Schinzel Robert T, Lewis Gregory D, Dejam A, Lee Y-K, Palma Melinda J, Calhoun S, Georgiadi A, Chen M-H, Ramachandran Vasan S, Larson Martin G, Bouchard C, Rankinen T, Souza Amanda L, Clish Clary B, Wang Thomas J, Estall Jennifer L, Soukas Alexander A, Cowan Chad A, Spiegelman Bruce M, Gerszten Robert E: Beta-Aminoisobutyric Acid Induces Browning of White Fat and Hepatic ²-Oxidation and Is Inversely Correlated with Cardiometabolic Risk Factors. Cell metabol