2-Aminoisobutyric acid

From Wikipedia, the free encyclopedia
  (Redirected from 2-aminoisobutyric acid)
Jump to: navigation, search
For other uses, see AIB (disambiguation).
2-Aminoisobutyric acid
2-aminoisobutyric acid.svg
2-methylalanine molecule
Names
IUPAC name
2-Amino-2-methylpropanoic acid
Other names
α-Aminoisobutyric acid
2-Methylalanine
Identifiers
62-57-7 YesY
ChEBI CHEBI:27971 YesY
ChemSpider 5891 YesY
DrugBank DB02952 YesY
EC-number 200-544-0
Jmol-3D images Image
KEGG C03665 YesY
PubChem 6119
Properties
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)
soluble
Acidity (pKa) 2.36 (carboxyl), 10.21 (amino)[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/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, p. 29 .