Open AccessA Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
Author(s) -
Matteo Pollastrini,
Filippo Lipparini,
Luca Pasquinelli,
Federica Balzano,
Gloria Uccello Barretta,
Gennaro Pescitelli,
Gaetano Angelici
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c00184
Subject(s) - indoline , proline , isomerization , chemistry , carboxylic acid , amide , carboxylate , solvent , peptide bond , stereochemistry , organic chemistry , amino acid , catalysis , enzyme , biochemistry
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.