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]
^"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.; Collective Volume, 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. PMC5728406. 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. PMC5993425. PMID 29367962.
December 01, 2023
aminoisobutyric, acid, also, known, aminoisobutyric, acid, methylalanine, methylalanine, proteinogenic, amino, acid, with, structural, formula, cooh, rare, nature, having, been, only, found, meteorites, some, antibiotics, fungal, origin, such, alamethicin, som. 2 Aminoisobutyric acid also known as a aminoisobutyric acid AIB a 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 2 Aminoisobutyric acid NamesPreferred IUPAC name 2 Amino 2 methylpropanoic acidOther names a Aminoisobutyric acid2 MethylalanineIdentifiersCAS Number 62 57 7 Y3D model JSmol Interactive imageChEBI CHEBI 27971 YChemSpider 5891 YDrugBank DB02952 YECHA InfoCard 100 000 495EC Number 200 544 0KEGG C03665 YPubChem CID 6119UNII 1E7ZW41IQU YCompTox Dashboard EPA DTXSID0058772InChI InChI 1S C4H9NO2 c1 4 2 5 3 6 7 h5H2 1 2H3 H 6 7 YKey FUOOLUPWFVMBKG UHFFFAOYSA N YInChI 1 C4H9NO2 c1 4 2 5 3 6 7 h5H2 1 2H3 H 6 7 Key FUOOLUPWFVMBKG UHFFFAOYADSMILES O C O C N C CPropertiesChemical formula C 4H 9N O 2Molar mass 103 12 g molAppearance white crystalline powderDensity 1 09 g mLBoiling point 204 4 C 399 9 F 477 5 K Solubility in water solubleAcidity pKa 2 36 carboxyl H2O 10 21 amino H2O 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Synthesis 2 Biological activity 3 Ribosomal incorporation into peptides 4 ReferencesSynthesis editIn 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 edit2 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 editSee also Cell free system and Cell free protein synthesis 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 References edit 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 a Aminoisobutyric acid Organic Syntheses 11 4 Collective Volume 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 lt 396 AID BIP10184 gt 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 amp Biomolecular Chemistry 16 7 1073 1078 doi 10 1039 c7ob02931d ISSN 1477 0539 PMC 5993425 PMID 29367962 Retrieved from https en wikipedia org w index php title 2 Aminoisobutyric acid amp oldid 1175938361, wikipedia, wiki, book, books, library,
