2-Aminoisobutyric acid

2-Aminoisobutyric acid

Names
IUPAC name 2-Amino-2-methylpropanoic acid
Other names α-Aminoisobutyric acid 2-Methylalanine
Identifiers
CAS Number	62-57-7
ChEBI	CHEBI:27971
ChemSpider	5891
DrugBank	DB02952
EC Number	200-544-0
Jmol 3D model	Interactive image
KEGG	C03665
PubChem	6119
InChI InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) Key: FUOOLUPWFVMBKG-UHFFFAOYSA-N 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 (pKa)	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).
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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

1. Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
2. Clarke, H. T.; Bean, H. J. (1931). "α-Aminoisobutyric acid". Org. Synth. 11: 4.; Coll. Vol. 2, p. 29.