2-Aminoisobutyric acid

changed 477197928 2-Aminoisobutyric acid 2-aminoisobutyric acid.svg skin-invert-image 170 2-Methylalanine-3D-balls.png bg-transparent 180 2-methylalanine molecule 2-Amino-2-methylpropanoic acid α-Aminoisobutyric acid2-Methylalanineα-methylalanine correct chemspider 5891 correct kegg C03665 1/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) correct EBI 27971 O=C(O)C(N)(C)C FUOOLUPWFVMBKG-UHFFFAOYAD correct chemspider 1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) correct chemspider FUOOLUPWFVMBKG-UHFFFAOYSA-N 62-57-7 correct CAS correct FDA 1E7ZW41IQU 200-544-0 6119 correct drugbank DB02952 4 9 1 2 103.12 g/mol white crystalline powder soluble 1.09 g/mL 204.4 2.36 (carboxyl; H2O) 10.21 (amino; H2O) Haynes, William M. 2016 CRC Handbook of Chemistry and Physics 97th CRC Press 978-1498754286 5–88 CRC Handbook of Chemistry and Physics 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 productsDas Manoj K. Raghothama S. Balaram P. Membrane channel forming polypeptides. Molecular conformation and mitochondrial uncoupling activity of antiamoebin, an .alpha.-aminoisobutyric acid containing peptide Biochemistry 1986 25 22 7110–7117 10.1021/bi00370a053 2432929 Synthesis and structure 2-Aminoisobutyric acid can be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis. Clarke H. T. Bean H. J. α-Aminoisobutyric acid 1931 11 4 10.15227/orgsyn.011.0004. The compound is not chiral, unlike most amino acids. It is a strong helix inducer in peptides due to Thorpe–Ingold effect of its gem-dimethyl group.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 10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7 0006-3525 12209474Misra Rajkumar Rudnick-Glick Safra Adler-Abramovich Lihi From Folding to Assembly: Functional Supramolecular Architectures of Peptides Comprised y of Non-Canonical Amino Acids Macromolecular Bioscience 2021 21 8 2100090 10.1002/mabi.202100090 34142442 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. FlexizymesOhuchi Masaki Murakami Hiroshi Suga Hiroaki The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus Current Opinion in Chemical Biology 11 5 537–542 10.1016/j.cbpa.2007.08.011 17884697 2007 and an engineered tRNA body enhance the affinity of aminoacylated Aib-tRNA species to elongation factor P.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 en 45 22 12601–12610 10.1093/nar/gkx1129 29155943 0305-1048 5728406 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.Iqbal Emil S. Dods Kara K. Hartman Matthew C. T. Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase Organic & Biomolecular Chemistry 16 7 1073–1078 en 10.1039/c7ob02931d 29367962 5993425 1477-0539 2018 Other occurrences Aib has been found in meteoritesImmune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms http://www.sci-news.com/space/mammalian-immune-system-extraterrestrial-microorganisms-08668.html Science News 23 July 2020 24 July 2020 and some antibiotics of fungal origin, such as alamethicin and some lantibiotics. References Category:Branched-chain amino acids Category:Non-proteinogenic amino acids Category:Alpha-amino acids