A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (

Autor: Matteo, Pollastrini, Filippo, Lipparini, Luca, Pasquinelli, Federica, Balzano, Gloria Uccello, Barretta, Gennaro, Pescitelli, Gaetano, Angelici
Rok vydání: 2021
Předmět:
Zdroj: The Journal of Organic Chemistry
ISSN: 1520-6904
Popis: A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.
Databáze: OpenAIRE