Α-aminoisobutyric acid

2-Aminoisobutyric acid

Names
IUPAC name 2-Amino-2-methylpropanoic acid
Other names α-Aminoisobutyric acid 2-Methylalanine
Identifiers
CAS Number	62-57-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27971 Y
ChemSpider	5891 Y
DrugBank	DB02952 Y
ECHA InfoCard	100.000.495
EC Number	200-544-0
KEGG	C03665 Y
PubChem CID	6119
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
SMILES O=C(O)C(N)(C)C
Properties
Chemical formula	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)
Solubility in water	soluble
Acidity (pKa)	2.36 (carboxyl), 10.21 (amino)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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 is rather rare in nature (cf. non-proteinogenic amino acids).

In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis. Industrial scale synthesis can be achieved by the selective hydroamination of methacrylic acid.

2-Aminoisobutyric acid is not one of the proteinogenic amino acids and is rather rare in nature (cf. non-proteinogenic amino acids). It is a strong helix inducer in peptides. Oligomers of AIB form 3₁₀ helices. BAIBA, or 3-aminoisobutyric acid, 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.

Several reports have confirmed the compatibility of 2-Aminoisobutyric acid with ribosomal elongation of peptide synthesis. Katoh et al. used flexizymes and an engineered a tRNA body to enhance the affinity of aminoacylated AIB-tRNA species to elongation factor-P. The result was an increased incorporation of AIB into peptides in a cell free translation system. Iqbal et al. used an alternative approach of creating an editing deficient valine tRNA-ligase to synthesize aminoacylated AIB-tRNA^Val. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.