2-Aminoisobutyric acid

Synthesis

In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis. Industrial scale synthesis could be achieved by the selective hydroamination of methacrylic acid, although this specific reaction has not been reported.

Biological activity

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. Oligomers of AIB form 310 helices.

Ribosomal incorporation into peptides

2-Aminoisobutyric acid is compatible with ribosomal elongation of peptide synthesis. Katoh et al. used flexizymes and an engineered 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-tRNAVal. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.

References

References

1. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
2. (23 July 2020). "Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms". Science News.
3. (1931). "α-Aminoisobutyric acid".
4. (2001). "Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution)". Biopolymers.
5. (2007). "The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus". Current Opinion in Chemical Biology.
6. (2017-12-15). "Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation". Nucleic Acids Research.
7. (2018). "Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase". Organic & Biomolecular Chemistry.