2-Aminoisobutyric acid

2-Aminoisobutyric acid
Names
	Preferred IUPAC name 2-Amino-2-methylpropanoic acid
	Other names α-Aminoisobutyric acid; 2-Methylalanine
Identifiers
CAS Number	62-57-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27971 ;
ChemSpider	5891 ;
DrugBank	DB02952 ;
ECHA InfoCard	100.000.495
EC Number	200-544-0;
KEGG	C03665 ;
PubChem CID	6119;
UNII	1E7ZW41IQU ;
CompTox Dashboard (EPA)	DTXSID0058772 ;
	InChI InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) Key: FUOOLUPWFVMBKG-UHFFFAOYSA-N ; 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; H2O); 10.21 (amino; H2O);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

Synthesis

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.

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.^[4] 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^[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-tRNA^Val. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.^[7]

References

^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–88. ISBN 978-1498754286.
^ "Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms". Science News. 23 July 2020. Retrieved 24 July 2020.
^ Clarke, H. T.; Bean, H. J. (1931). "α-Aminoisobutyric acid". Organic Syntheses. 11: 4; Collected Volumes, vol. 2, p. 29..
^ Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. (2001). "Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution)". Biopolymers. 60 (6): 396–419. doi:10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7. ISSN 0006-3525. PMID 12209474.
^ Ohuchi, Masaki; Murakami, Hiroshi; Suga, Hiroaki (2007). "The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus". Current Opinion in Chemical Biology. 11 (5): 537–542. doi:10.1016/j.cbpa.2007.08.011. PMID 17884697.
^ Katoh, Takayuki; Iwane, Yoshihiko; Suga, Hiroaki (2017-12-15). "Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation". Nucleic Acids Research. 45 (22): 12601–12610. doi:10.1093/nar/gkx1129. ISSN 0305-1048. PMC 5728406. PMID 29155943.
^ Iqbal, Emil S.; Dods, Kara K.; Hartman, Matthew C. T. (2018). "Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase". Organic & Biomolecular Chemistry. 16 (7): 1073–1078. doi:10.1039/c7ob02931d. ISSN 1477-0539. PMC 5993425. PMID 29367962.

[CRC97-1] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–88. ISBN 978-1498754286.

[2] "Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms". Science News. 23 July 2020. Retrieved 24 July 2020.

[3] Clarke, H. T.; Bean, H. J. (1931). "α-Aminoisobutyric acid". Organic Syntheses. 11: 4; Collected Volumes, vol. 2, p. 29..

[4] Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. (2001). "Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution)". Biopolymers. 60 (6): 396–419. doi:10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7. ISSN 0006-3525. PMID 12209474.

[5] Ohuchi, Masaki; Murakami, Hiroshi; Suga, Hiroaki (2007). "The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus". Current Opinion in Chemical Biology. 11 (5): 537–542. doi:10.1016/j.cbpa.2007.08.011. PMID 17884697.

[6] Katoh, Takayuki; Iwane, Yoshihiko; Suga, Hiroaki (2017-12-15). "Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation". Nucleic Acids Research. 45 (22): 12601–12610. doi:10.1093/nar/gkx1129. ISSN 0305-1048. PMC 5728406. PMID 29155943.

[7] Iqbal, Emil S.; Dods, Kara K.; Hartman, Matthew C. T. (2018). "Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase". Organic & Biomolecular Chemistry. 16 (7): 1073–1078. doi:10.1039/c7ob02931d. ISSN 1477-0539. PMC 5993425. PMID 29367962.

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