Issue 46, 2018

Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2018,9, 8753-8759

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements