2-Aminoisobutyric acid

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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
3D model (Jmol) Interactive image
ChEBI CHEBI:27971 YesY
ChemSpider 5891 YesY
DrugBank DB02952 YesY
ECHA InfoCard 100.000.495
EC Number 200-544-0
KEGG C03665 YesY
PubChem 6119
Properties
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)
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).
YesY verify (what is YesYN ?)
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[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 .

BAIBA is found as a normal metabolite of skeletal muscle in 2014. The plasma concentrations are increased in human by exercise. The production is likely a result of enhanced mitochondrial activity as the increase is also observed in the muscle of PGC-1a overexpression mice. BAIBA is proposed as protective factor against metabolic disorder since it can induce brown fat function.

Roberts Lee D, Boström P, O Sullivan John F, Schinzel Robert T, Lewis Gregory D, Dejam A, Lee Y-K, Palma Melinda J, Calhoun S, Georgiadi A, Chen M-H, Ramachandran Vasan S, Larson Martin G, Bouchard C, Rankinen T, Souza Amanda L, Clish Clary B, Wang Thomas J, Estall Jennifer L, Soukas Alexander A, Cowan Chad A, Spiegelman Bruce M, Gerszten Robert E: Beta-Aminoisobutyric Acid Induces Browning of White Fat and Hepatic ²-Oxidation and Is Inversely Correlated with Cardiometabolic Risk Factors. Cell metabolism 2014;19:96-108