(E)-Ethyl-2-cyano-2-(((2,4,6-trichlorobenzoyl)oxy)imino)acetate: A Modified Yamaguchi Reagent for Enantioselective Esterification, Thioesterification, Amidation, and Peptide Synthesis
| Autor: | Sandip Mondal, Srinivasa Rao Manne, Jyoti Chandra, Bhubaneswar Mandal |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
General Chemical Engineering Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Article 0104 chemical sciences lcsh:Chemistry chemistry.chemical_compound chemistry lcsh:QD1-999 Reagent Amide Peptide synthesis Peptide bond Dimethylformamide Racemization Dichloromethane |
| Zdroj: | ACS Omega ACS Omega, Vol 3, Iss 6, Pp 6120-6133 (2018) |
| ISSN: | 2470-1343 |
| Popis: | Here, the synthesis and applications of (E)-ethyl-2-cyano-2-(((2,4,6-trichlorobenzoyl)oxy)imino)acetate as a racemization suppressing and easily recyclable version of the Yamaguchi reagent that can be used for amide and peptide synthesis are reported. We demonstrated its application in racemization-free esterification, thioesterification, amidation, and peptide bond formation. We successfully synthesized oligopeptides on the solid support in dimethylformamide as well as in solution (dichloromethane) by applying this coupling reagent. It is important to note that a mixed-anhydride-based method provides peptide-forming reactions as good as the current methods using built-in coupling reagents. Mechanism investigation, racemization suppression, and recyclability are also discussed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|