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A0685 Sigma

α-Aminoisobutyric acid-carboxy-14C hydrochloride

≥98% (Radiochemical Purity, HPLC), aqueous ethanol solution

Synonym: 2-Methylalanine

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Properties

assay   ≥98% (Radiochemical Purity, HPLC)
form   aqueous ethanol solution
extent of labeling   1-15 mCi per mmol
storage temp.   2-8°C

Description

Packaging

Combi-vial

Physical form

Aqueous solution containing 2% ethanol

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Safety & Documentation

Safety Information

RIDADR 
UN 2910 7
WGK Germany 
-

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Analysis of the amide (15)N chemical shift tensor of the C(alpha) tetrasubstituted constituent of membrane-active peptaibols, the alpha-aminoisobutyric acid residue, compared to those of di- and tri-substituted proteinogenic amino acid residues. Salnikov E, Bertani P, Raap J, et al. J. Biomol. NMR 45(4), 373-87, (2009)

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Stapling of a 3(10)-helix with click chemistry. Jacobsen Ø, Maekawa H, Ge NH, et al. J. Org. Chem. 76(5), 1228-38, (2011)

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UVolution, a photochemistry experiment in low earth orbit: investigation of the photostability of carboxylic acids exposed to mars surface UV radiation conditions. Stalport F, Guan YY, Coll P, et al. Astrobiology 10(4), 449-61, (2010)

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Heptanuclear heterometallic [Cu6Ln] clusters: trapping lanthanides into copper cages with artificial amino acids. Sopasis GJ, Canaj AB, Philippidis A, et al. Inorg. Chem. 51(10), 5911-8, (2012)

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In silico interpretation of cw-ESR at 9 and 95 GHz of mono- and bis- TOAC-labeled Aib-homopeptides in fluid and frozen acetonitrile. Carlotto S, Zerbetto M, Shabestari MH, et al. J. Phys. Chem. B 115(44), 13026-36, (2011)

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Charge mapping in 3(10)-helical peptide chains by oxidation of the terminal ferrocenyl group. Donoli A, Marcuzzo V, Moretto A, et al. Org. Lett. 13(6), 1282-5, (2011)

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Distribution and stable isotopic composition of amino acids from fungal peptaibiotics: assessing the potential for meteoritic contamination. Elsila JE, Callahan MP, Glavin DP, et al. Astrobiology 11(2), 123-33, (2011)

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Effect of a strong interfacial electric field on the orientation of the dipole moment of thiolated aib-oligopeptides tethered to mercury on either the N- or C-terminus. Becucci L, Guryanov I, Maran F, et al. J. Am. Chem. Soc. 132(17), 6194-204, (2010)

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The effects of isoflurane pretreatment on cerebral blood flow, capillary permeability, and oxygen consumption in focal cerebral ischemia in rats. Chi OZ, Hunter C, Liu X, et al. Anesth. Analg. 110(5), 1412-8, (2010)

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Methyl jasmonate-induced defense responses are associated with elevation of 1-aminocyclopropane-1-carboxylate oxidase in Lycopersicon esculentum fruit. Yu M, Shen L, Zhang A, et al. J. Plant Physiol. 168(15), 1820-7, (2011)

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Conformations of peptides containing a chiral cyclic α, α-disubstituted α-amino acid within the sequence of Aib residues. Demizu Y, Tanaka M, Doi M, et al. J. Pept. Sci. 16(11), 621-6, (2010)

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Mixed quantum classical simulations of excitons in peptide helices. Goj A and Bittner ER J. Chem. Phys. 134(20), 205103, (2011)

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Antimicrobial lipopeptaibol trichogin GA IV: role of the three Aib residues on conformation and bioactivity. De Zotti M, Biondi B, Park Y, et al. Amino Acids 43(4), 1761-77, (2012)

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Conformations of helical Aib peptides containing a pair of L-amino acid and D-amino acid. Demizu Y, Yabuki YU, Doi M, et al. J. Pept. Sci. 18(7), 466-75, (2012)

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Evaluation of functional groups on amino acids in cyclic tetrapeptides in histone deacetylase inhibition. Islam MS, Bhuiyan MP, Islam MN, et al. Amino Acids 42(6), 2103-10, (2012)

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Replacement of Ala by Aib improves structuration and biological stability in thymine-based alpha-nucleopeptides. Geotti-Bianchini P, Moretto A, Peggion C, et al. Org. Biomol. Chem. 8(6), 1315-21, (2010)

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Twisted structure of a cyclic hexapeptide containing a combination of alternating L-Leu-D-Leu-Aib segments. Demizu Y, Nagoya S, Doi M, et al. J. Org. Chem. 77(20), 9361-5, (2012)

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Cellular uptake of Aib-containing amphipathic helix peptide. Wada S, Tsuda H, Okada T, et al. Bioorg. Med. Chem. Lett. 21(19), 5688-91, (2011)

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An efficient and expedient method for the synthesis of 11C-labeled α-aminoisobutyric acid: a tumor imaging agent potentially useful for cancer diagnosis. Kato K, Tsuji AB, Saga T, Zhang MR. Bioorg. Med. Chem. Lett. 21, 2437-2440, (2011)

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Effects of GABA(A) receptor blockade on regional cerebral blood flow and blood-brain barrier disruption in focal cerebral ischemia. Chi OZ, Hunter C, Liu X, et al. J. Neurol. Sci. 301(1-2), 66-70, (2011)

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Glycine enhances microglial intracellular calcium signaling. A role for sodium-coupled neutral amino acid transporters. Van den Eynden J, Notelaers K, Brône B, et al. Pflugers Arch. 461(4), 481-91, (2011)

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Comparison of 2-amino-[3-¹¹C]isobutyric acid and 2-deoxy-2-[¹⁸F]fluoro-D-glucose in nude mice with xenografted tumors and acute inflammation. Tsuji AB, Kato K, Sugyo A, et al. Nucl. Med. Commun. 33(10), 1058-64, (2012)

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Formation of vesicles through solvent assisted self-assembly of hydrophobic pentapeptides: encapsulation and pH responsive release of dyes by the vesicles. Kar S, Drew MG, and Pramanik A Protein Pept. Lett. 18(9), 886-97, (2011)

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Overlapping double turn conformations adopted by tetrapeptides containing non-coded alpha-amino isobutyric acid (Aib) and formation of tape-like structures through supramolecular helix mediated self-assembly. Kar S, Dutta A, Drew MG, et al. Protein Pept. Lett. 16(9), 1063-73, (2009)

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Specificity of the volume-activated amino acid efflux pathway in cultured human breast cancer cells. Shennan DB and Thomson J Gen. Physiol. Biophys. 30(1), 45-51, (2011)

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