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

[Image: see text] 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 amid...

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Autores principales: Pollastrini, Matteo, Lipparini, Filippo, Pasquinelli, Luca, Balzano, Federica, Barretta, Gloria Uccello, Pescitelli, Gennaro, Angelici, Gaetano
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456495/
https://www.ncbi.nlm.nih.gov/pubmed/34080867
http://dx.doi.org/10.1021/acs.joc.1c00184
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author Pollastrini, Matteo
Lipparini, Filippo
Pasquinelli, Luca
Balzano, Federica
Barretta, Gloria Uccello
Pescitelli, Gennaro
Angelici, Gaetano
author_facet Pollastrini, Matteo
Lipparini, Filippo
Pasquinelli, Luca
Balzano, Federica
Barretta, Gloria Uccello
Pescitelli, Gennaro
Angelici, Gaetano
author_sort Pollastrini, Matteo
collection PubMed
description [Image: see text] 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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spelling pubmed-84564952021-09-23 A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives Pollastrini, Matteo Lipparini, Filippo Pasquinelli, Luca Balzano, Federica Barretta, Gloria Uccello Pescitelli, Gennaro Angelici, Gaetano J Org Chem [Image: see text] 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. American Chemical Society 2021-06-03 2021-06-18 /pmc/articles/PMC8456495/ /pubmed/34080867 http://dx.doi.org/10.1021/acs.joc.1c00184 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Pollastrini, Matteo
Lipparini, Filippo
Pasquinelli, Luca
Balzano, Federica
Barretta, Gloria Uccello
Pescitelli, Gennaro
Angelici, Gaetano
A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title_full A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title_fullStr A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title_full_unstemmed A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title_short A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
title_sort proline mimetic for the design of new stable secondary structures: solvent-dependent amide bond isomerization of (s)-indoline-2-carboxylic acid derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456495/
https://www.ncbi.nlm.nih.gov/pubmed/34080867
http://dx.doi.org/10.1021/acs.joc.1c00184
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