2-Aminoisobutyric acid

For other uses, see AIB (disambiguation).

2-Aminoisobutyric acid
Names


IUPAC name 2-Amino-2-methylpropanoic acid
Other names α-Aminoisobutyric acid 2-Methylalanine
Identifiers
CAS Number	62-57-7^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27971^Y
ChemSpider	5891^Y
DrugBank	DB02952^Y
ECHA InfoCard	100.000.495
EC Number	200-544-0
KEGG	C03665^Y
PubChem	6119
InChI InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)^Y Key: FUOOLUPWFVMBKG-UHFFFAOYSA-N^Y InChI=1/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) Key: FUOOLUPWFVMBKG-UHFFFAOYAD
SMILES O=C(O)C(N)(C)C
Properties
Chemical formula	C₄H₉NO₂
Molar mass	103.12 g/mol
Appearance	white crystalline powder
Density	1.09 g/mL
Boiling point	204.4 °C (399.9 °F; 477.5 K)
Solubility in water	soluble
Acidity (pK_a)	2.36 (carboxyl), 10.21 (amino)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

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.^[2]

References

↑ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
↑ Clarke, H. T.; Bean, H. J. (1931). "α-Aminoisobutyric acid". Org. Synth. 11: 4. ; Coll. Vol., 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 metabolism 2014;19:96-108

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