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Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemistʼs Toolbox
[Image: see text] Over the years, numerous modifications to the structure of proline have been made in order to tune its effects on bioactive compounds. Notably, the introduction of a cyclopropane ring or a fluorine atom has produced interesting results. Herein, we describe the synthesis of a prolin...
Autores principales: | , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8851640/ https://www.ncbi.nlm.nih.gov/pubmed/35187307 http://dx.doi.org/10.1021/acsomega.1c05337 |
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author | Pons, Amandine Decaens, Jonathan Najjar, Riham Otog, Nansalmaa Arribat, Mathieu Jolly, Sandrine Couve-Bonnaire, Samuel Sebban, Muriel Coadou, Gael Oulyadi, Hassan Speybrouck, David Iwasa, Seiji Charette, André B. Poisson, Thomas Jubault, Philippe |
author_facet | Pons, Amandine Decaens, Jonathan Najjar, Riham Otog, Nansalmaa Arribat, Mathieu Jolly, Sandrine Couve-Bonnaire, Samuel Sebban, Muriel Coadou, Gael Oulyadi, Hassan Speybrouck, David Iwasa, Seiji Charette, André B. Poisson, Thomas Jubault, Philippe |
author_sort | Pons, Amandine |
collection | PubMed |
description | [Image: see text] Over the years, numerous modifications to the structure of proline have been made in order to tune its effects on bioactive compounds. Notably, the introduction of a cyclopropane ring or a fluorine atom has produced interesting results. Herein, we describe the synthesis of a proline containing fluorocyclopropane. This modified amino acid was inserted into a tripeptide, whose conformation was studied by nuclear magnetic resonance and density functional theory calculations. |
format | Online Article Text |
id | pubmed-8851640 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-88516402022-02-18 Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemistʼs Toolbox Pons, Amandine Decaens, Jonathan Najjar, Riham Otog, Nansalmaa Arribat, Mathieu Jolly, Sandrine Couve-Bonnaire, Samuel Sebban, Muriel Coadou, Gael Oulyadi, Hassan Speybrouck, David Iwasa, Seiji Charette, André B. Poisson, Thomas Jubault, Philippe ACS Omega [Image: see text] Over the years, numerous modifications to the structure of proline have been made in order to tune its effects on bioactive compounds. Notably, the introduction of a cyclopropane ring or a fluorine atom has produced interesting results. Herein, we describe the synthesis of a proline containing fluorocyclopropane. This modified amino acid was inserted into a tripeptide, whose conformation was studied by nuclear magnetic resonance and density functional theory calculations. American Chemical Society 2022-02-04 /pmc/articles/PMC8851640/ /pubmed/35187307 http://dx.doi.org/10.1021/acsomega.1c05337 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Pons, Amandine Decaens, Jonathan Najjar, Riham Otog, Nansalmaa Arribat, Mathieu Jolly, Sandrine Couve-Bonnaire, Samuel Sebban, Muriel Coadou, Gael Oulyadi, Hassan Speybrouck, David Iwasa, Seiji Charette, André B. Poisson, Thomas Jubault, Philippe Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title | Fluorocyclopropane-Containing Proline Analogue: Synthesis
and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title_full | Fluorocyclopropane-Containing Proline Analogue: Synthesis
and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title_fullStr | Fluorocyclopropane-Containing Proline Analogue: Synthesis
and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title_full_unstemmed | Fluorocyclopropane-Containing Proline Analogue: Synthesis
and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title_short | Fluorocyclopropane-Containing Proline Analogue: Synthesis
and Conformation of an Item in the Peptide Chemistʼs Toolbox |
title_sort | fluorocyclopropane-containing proline analogue: synthesis
and conformation of an item in the peptide chemistʼs toolbox |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8851640/ https://www.ncbi.nlm.nih.gov/pubmed/35187307 http://dx.doi.org/10.1021/acsomega.1c05337 |
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