3D model (JSmol)
|Molar mass||103.12 g/mol|
|Appearance||white crystalline powder|
|Boiling point||204.4 °C (399.9 °F; 477.5 K)|
|Acidity (pKa)||2.36 (carboxyl), 10.21 (amino)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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).
In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis. Industrial scale synthesis can be achieved by the selective hydroamination of methacrylic acid.
2-Aminoisobutyric acid is not one of the proteinogenic amino acids and rather rare in nature (cf. non-proteinogenic amino acids). It is a strong helix inducer in peptides. Oligomers of AIB form 310 helices. 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.
- 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.
- 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. "β-Aminoisobutyric acid induces browning of white fat and hepatic β-oxidation and is inversely correlated with cardiometabolic risk factors". Cell Metabolism 2014;19:96–108.