2-Aminoisobutyric acid
Chemical compound
From Wikipedia, the free encyclopedia
2-Aminoisobutyric acid (Aib) is the non-proteinogenic amino acid with the structural formula H2N-C(CH3)2-COOH. The Aib residue is a component of tirzepatide, a commonly prescribed antidiabetic medication for treatment of type 2 diabetes. Although uncommon, it is also found in some natural products[2][3]
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| Names | |
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| Preferred IUPAC name
2-Amino-2-methylpropanoic acid | |
| Other names
α-Aminoisobutyric acid 2-Methylalanine α-methylalanine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.495 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
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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Synthesis and structure
2-Aminoisobutyric acid can be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis.[4]
The compound is not chiral, unlike most amino acids. It is a strong helix inducer in peptides due to ThorpeâIngold effect of its gem-dimethyl group.[5][3] Oligomers of Aib form 310 helices.
Biological activity
2-Aminoisobutyric acid is not one of the proteinogenic amino acids and is rather rare in nature (cf. non-proteinogenic amino acids). In the context of cell-free protein synthesis 2-aminoisobutyric acid is compatible with ribosomal elongation of peptide synthesis. Flexizymes[6] and an engineered tRNA body enhance the affinity of aminoacylated Aib-tRNA species to elongation factor P.[7] 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 valineâtRNA ligase to synthesize aminoacylated Aib-tRNAVal. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield Aib-containing peptides.[8]
Other occurrences
Aib has been found in meteorites[9] and some antibiotics of fungal origin, such as alamethicin and some lantibiotics.