2-Aminoisobutyric acid

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For other uses, see AIB (disambiguation).
2-Aminoisobutyric acid
2-aminoisobutyric acid.svg
2-methylalanine molecule
Identifiers
CAS number 62-57-7 YesY
PubChem 6119
ChemSpider 5891 YesY
EC-number 200-544-0
DrugBank DB02952
KEGG C03665 YesY
ChEBI CHEBI:27971 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H9NO2
Molar mass 103.12 g mol−1
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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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. 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[edit]

  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: 29 .