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Issue 46, 2018
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Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

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Abstract

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.

Graphical abstract: Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

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Supplementary files

Article information


Submitted
30 May 2018
Accepted
18 Sep 2018
First published
20 Sep 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 8753-8759
Article type
Edge Article

Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

D. Montoir, M. Amoura, Z. E. A. Ababsa, T. M. Vishwanatha, E. Yen-Pon, V. Robert, M. Beltramo, V. Piller, M. Alami, V. Aucagne and S. Messaoudi, Chem. Sci., 2018, 9, 8753
DOI: 10.1039/C8SC02370K

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