Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation

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 unprot...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018-12, Vol.9 (46), p.8753-8759
Main Authors: Montoir, David, Amoura, Mehdi, Ababsa, Zine El Abidine, Vishwanatha, T M, Yen-Pon, Expédite, Robert, Vincent, Beltramo, Massimiliano, Piller, Véronique, Alami, Mouad, Aucagne, Vincent, Messaoudi, Samir
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical Sciences
Chemistry
Conjugation
Organic chemistry
Other
Peptides
Solid phases
Substrates
Synthesis
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Summary: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- -GlcNAc- and α- -GalNAc-derivatives into very long unprotected peptides. This study opens the way to new applications in chemical biology, considering the well-recognized advantages of -glycosides over -glycosides in terms of resistance towards both enzymatic and chemical degradation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc02370k