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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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Publication details

The article was received on 30 May 2018, accepted on 18 Sep 2018 and first published on 20 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC02370K
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C8SC02370K

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