2-Aminoisobutyric acid (also known as α-aminoisobutyric acid, AIB, α-methylalanine, or 2-methylalanine) is the non-proteinogenic amino acid with the structural formula H2N-C(CH3)2-COOH. It is rare in nature, having been only found in meteorites,[2] and some antibiotics of fungal origin, such as alamethicin and some lantibiotics.
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Preferred IUPAC name
2-Amino-2-methylpropanoic acid | |
Other names
α-Aminoisobutyric acid
2-Methylalanine | |
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ChEBI |
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ECHA InfoCard | 100.000.495 |
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CompTox Dashboard (EPA)
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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) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis.[3] 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 due to Thorpe–Ingold effect of its gem-dimethyl group.[4] Oligomers of AIB form 310 helices.
2-Aminoisobutyric acid is compatible with ribosomal elongation of peptide synthesis. Katoh et al. used flexizymes[5] and an engineered a tRNA body to enhance the affinity of aminoacylated AIB-tRNA species to elongation factor P.[6] 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-tRNAVal. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.[7]