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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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.
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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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