Accelerated solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites

Org Biomol Chem. 2023 Feb 22;21(8):1674-1679. doi: 10.1039/d2ob01886a.

Abstract

Peptide fragments of glycoproteins containing multiple N-glycosylated sites are essential biochemical tools not only to investigate protein-protein interactions but also to develop glycopeptide-based diagnostics and immunotherapy. However, solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites is hampered by difficult couplings, which results in a substantial drop in yield. To increase the final yield, large amounts of reagents but also time-consuming steps are required. Therefore, we propose herein to utilize heating and stirring in combination with low-loading solid supports to set up an accelerated route to obtain, by an efficient High-Temperature Fast Stirring Peptide Synthesis (HTFS-PS), glycopeptides containing multiple N-glycosylated sites using equimolar excess of the precious glycosylated building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycopeptides*
  • Glycoproteins
  • Glycosylation
  • Solid-Phase Synthesis Techniques*

Substances

  • Glycopeptides
  • Glycoproteins