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2-Aminoisobutyric acid

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This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 13:04, 20 October 2011 (Updating {{chembox}}, {{drugbox}} (changes to verified fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|b...). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 13:04, 20 October 2011 by CheMoBot (talk | contribs) (Updating {{chembox}}, {{drugbox}} (changes to verified fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|b...)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) 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
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.495 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
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
Acidity (pKa) 2.36 (carboxyl), 10.21 (amino)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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". Organic Syntheses. 11: 4; Collected Volumes, vol. 2, p. 29..
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