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Continue to Iris Biotech GmbHSend request to US distributorChemischer Name: (2S,4R)-4-Trifluoromethyl-pseudoproline-benzyl ester // Synonyme: (2S,4R)-benzyl 2-(trifluoromethyl)oxazolidine-4-carboxylate
Startet von 400,00 €
The incorporation of trifluoromethyl group carrying building blocks into peptides results in increased chemical and thermal stability, increased resistance to degradation by proteases, and enhanced lipophilicity, i.e. better affinity to lipid membranes. Stabilization of particular conformations and auto-assembly can be induced. Also useful as label for 19F-NMR studies. ?-Trifluoromethyl substituted amino acids are, therefore, very attractive building blocks for the design of biologically active compounds.
Fluorine in Peptide Design and Protein Engineering; C. Jäckel and B. Koksch; Eur J. Org. Chem. 2005; 21: 4483-4503. https://doi.org/10.1002/ejoc.200500205
Conformational properties of peptides incorporating a fluorinated pseudoproline residue; G. Chaume, D. Feytens, G. Chassaing, S. Lavielle, T. Brigaud, E. Miclet; New J. Chem. 2013; 37: 1336-1342. https://doi.org/10.1039/C3NJ41084F
Impact of fluorination on proteolytic stability of peptides in human blood plasma; V. Asante, J. Mortier, H. Schlüter, B. Koksch; Bioorg. Med. Chem. 2013; 21: 3542-3546. https://doi.org/10.1016/j.bmc.2013.03.051.
Fluorinated Proteins: From Design and Synthesis to Structure and Stability; E. N. G. Marsh; Acc. Chem. Res. 2014; 47: 2878-2886. https://doi.org/10.1021/ar500125m
How Cα-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes: Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling; R. Smits, B. Koksch; Current Topics in Medicinal Chemistry 2006; 6: 1483-1498. https://doi.org/10.2174/156802606777951055
Approaches to Obtaining Fluorinated α-Amino Acids; J. Moschner, V. Stulberg, R. Fernandes, S. Huhmann, J. Leppkes, B. Koksch; Chem. Rev. 2019; 119: 10718-10801. https://doi.org/10.1021/acs.chemrev.9b00024
Applications of fluorine-containing amino acids for drug design; H. Mei, J. Han, K. D. Klika, K. Izawa, T. Sato, N. A. Meanwell, V. A. Soloshonok; Eur. J. Med. Chem. 2020; 186: 111826. https://doi.org/10.1016/j.ejmech.2019.111826
Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions; M. Salwiczek, E. K. Nyakatura, U. I. M. Gerling, S. Ye, B. Koksch; Chem. Soc. Rev. 2012; 41: 2135-2171. https://doi.org/10.1039/C1CS15241F
Substitution Effect of the Trifluoromethyl Group on the Bioactivity in Medicinal Chemistry: Statistical Analysis and Energy Calculations; A. Abula, Z. Xu, Z. Zhu, C. Peng, Z. Chen, W. Zhu, H. A. Aisa; J. Chem. Inf. Model 2020; https://doi.org/10.1021/acs.jcim.0c00898
Synthesis of an MIF-1 analogue containing enantiopure (S)-alpha-trifluoromethyl-proline and biological evaluation on nociception; I. Jlalia, N. Lensen, G. Chaume, E. Dzhambazova, L. Astasidi, R. Hadjiolova, A. Bocheva, T. Brigaud; Eur J Med Chem 2013; 62: 122-9. https://doi.org/10.1016/j.ejmech.2012.12.041
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