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

Bhavesh Premdjee; Anna L Adams; Derek Macmillan

doi:10.1016/j.bmcl.2011.05.059

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

Bioorg Med Chem Lett. 2011 Sep 1;21(17):4973-5. doi: 10.1016/j.bmcl.2011.05.059. Epub 2011 May 25.

Authors

Bhavesh Premdjee¹, Anna L Adams, Derek Macmillan

Affiliation

¹ Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid
Esters / chemistry*
Glycopeptides / chemical synthesis*
Glycopeptides / chemistry
Spectrometry, Mass, Electrospray Ionization

Substances

Esters
Glycopeptides

Grants and funding

WT_/Wellcome Trust/United Kingdom