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Montoir D., Amoura M., Ababsa Z. E. A., Vishwanatha T. M., Yen-Pon E., Robert V., Beltramo M., Piller V., Alami M., Aucagne V. and Messaoudi S.

Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation.

Chemical Science (2018)

par Frapart - publié le

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.

Voir en ligne : doi : 10.1039/C8SC02370K