A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives | Zendy

Matteo Pollastrini | Zendy; Filippo Lipparini | Zendy; Luca Pasquinelli | Zendy; Federica Balzano | Zendy; Gloria UccelloBarretta | Zendy; Gennaro Pescitelli | Zendy; Gaetano Angelici | Zendy

Open Access

A 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 UccelloBarretta,

Gennaro Pescitelli,

Gaetano Angelici

Publication year - 2021

Publication title -

the 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) - chemistry , indoline , isomerization , proline , carboxylic acid , amide , carboxylate , peptide bond , solvent , hydrogen bond , organic chemistry , stereochemistry , molecule , 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.

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