2-Aminoisobutyric acid

2-Aminoisobutyric acid

IUPAC name 2-Amino-2-methylpropanoic acid
Other names α-Aminoisobutyric acid 2-Methylalanine
Identifiers
CAS number	62-57-7^Y
PubChem	6119
ChemSpider	5891^Y
EC-number	200-544-0
DrugBank	EXPT00471
KEGG	C03665^Y
ChEBI	CHEBI:27971^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(N)(C)C
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
Properties
Molecular formula	C₄H₉NO₂
Molar mass	103.12 g mol⁻¹
Acidity (pK_a)	2.36 (carboxyl), 10.21 (amino)^[1]
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. α-Aminoisobutyric acid is a strong helix inducer in peptides. Its oligomers form 3-10 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, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0029 ; Coll. Vol. 2: 29 .