Native N-glycopeptide thioester synthesis through N→S acyl transfer.

Bioorg Med Chem Lett

Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.

Published: September 2011

Peptide thioesters are important tools for the total synthesis of proteins using native chemical ligation (NCL). Preparation of glycopeptide thioesters, that enable the assembly of homogeneously glycosylated proteins, is complicated by the perceived fragile nature of the sugar moiety. Herein, we demonstrate the compatibility of thioester formation via N→S acyl transfer with native N-glycopeptides and report observations that will aid in their preparation.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3160546PMC
http://dx.doi.org/10.1016/j.bmcl.2011.05.059DOI Listing

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