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

Poriah Strauss, Francesca Nuti, Michael Quagliata, Anna Maria Papini*, Mattan Hurevich*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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.

Original languageAmerican English
Pages (from-to)1674-1679
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume21
Issue number8
DOIs
StatePublished - 10 Nov 2022

Bibliographical note

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

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