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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6295873 | PMC |
| http://dx.doi.org/10.1039/c8sc02370k | DOI Listing |
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