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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.
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David Montoir, Mehdi Amora, Zine El Abidine Aabasa, Vishwanatha Thimmalapura Marulappa, Expédite Yen-Pon, et al.. Synthesis of aryl-thioglycopeptides through chemoselective Pd-Mediated conjugation. Chemical Science , The Royal Society of Chemistry, 2018, 9 (46), pp.8753-8759. ⟨10.1039/C8SC02370K⟩. ⟨hal-02622102⟩

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