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Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

We describe herein a Pd-catalyzed methodology for the thioglycoconjugation of iodoaryl peptides and aminoacids. This operationally simple process occurs under semi-aqueous conditions and displays wide substrate scope. The strategy has been successfully applied to both the thioglycosylation of unprot...

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Autores principales: Montoir, David, Amoura, Mehdi, Ababsa, Zine El Abidine, Vishwanatha, T. M., Yen-Pon, Expédite, Robert, Vincent, Beltramo, Massimiliano, Piller, Véronique, Alami, Mouad, Aucagne, Vincent, Messaoudi, Samir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6295873/
https://www.ncbi.nlm.nih.gov/pubmed/30627396
http://dx.doi.org/10.1039/c8sc02370k
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author Montoir, David
Amoura, Mehdi
Ababsa, Zine El Abidine
Vishwanatha, T. M.
Yen-Pon, Expédite
Robert, Vincent
Beltramo, Massimiliano
Piller, Véronique
Alami, Mouad
Aucagne, Vincent
Messaoudi, Samir
author_facet Montoir, David
Amoura, Mehdi
Ababsa, Zine El Abidine
Vishwanatha, T. M.
Yen-Pon, Expédite
Robert, Vincent
Beltramo, Massimiliano
Piller, Véronique
Alami, Mouad
Aucagne, Vincent
Messaoudi, Samir
author_sort Montoir, David
collection PubMed
description We describe herein a Pd-catalyzed methodology for the thioglycoconjugation of iodoaryl peptides and aminoacids. This operationally simple process occurs under semi-aqueous conditions and displays wide substrate scope. The strategy has been successfully applied to both the thioglycosylation of unprotected peptides and the generation of thioglyco-aminoacid building blocks, including those suitable for solid phase peptide synthesis. To demonstrate the broad potential of this technique for late stage functionalization, we successfully incorporated challenging unprotected β-S-GlcNAc- and α-S-GalNAc-derivatives into very long unprotected peptides. This study opens the way to new applications in chemical biology, considering the well-recognized advantages of S-glycosides over O-glycosides in terms of resistance towards both enzymatic and chemical degradation.
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spelling pubmed-62958732019-01-09 Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation Montoir, David Amoura, Mehdi Ababsa, Zine El Abidine Vishwanatha, T. M. Yen-Pon, Expédite Robert, Vincent Beltramo, Massimiliano Piller, Véronique Alami, Mouad Aucagne, Vincent Messaoudi, Samir Chem Sci Chemistry We describe herein a Pd-catalyzed methodology for the thioglycoconjugation of iodoaryl peptides and aminoacids. This operationally simple process occurs under semi-aqueous conditions and displays wide substrate scope. The strategy has been successfully applied to both the thioglycosylation of unprotected peptides and the generation of thioglyco-aminoacid building blocks, including those suitable for solid phase peptide synthesis. To demonstrate the broad potential of this technique for late stage functionalization, we successfully incorporated challenging unprotected β-S-GlcNAc- and α-S-GalNAc-derivatives into very long unprotected peptides. This study opens the way to new applications in chemical biology, considering the well-recognized advantages of S-glycosides over O-glycosides in terms of resistance towards both enzymatic and chemical degradation. Royal Society of Chemistry 2018-09-20 /pmc/articles/PMC6295873/ /pubmed/30627396 http://dx.doi.org/10.1039/c8sc02370k Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Montoir, David
Amoura, Mehdi
Ababsa, Zine El Abidine
Vishwanatha, T. M.
Yen-Pon, Expédite
Robert, Vincent
Beltramo, Massimiliano
Piller, Véronique
Alami, Mouad
Aucagne, Vincent
Messaoudi, Samir
Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title_full Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title_fullStr Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title_full_unstemmed Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title_short Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation
title_sort synthesis of aryl-thioglycopeptides through chemoselective pd-mediated conjugation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6295873/
https://www.ncbi.nlm.nih.gov/pubmed/30627396
http://dx.doi.org/10.1039/c8sc02370k
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