Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase

Niklas H. Fischer, Benedicte N. Vævest, Andreas K. Dam, Frederik Diness, Christian M. Pedersen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Self-promoted glycosylations with trichloroacetimidate glycosyl donors are demonstrated on solid-phase-anchored peptides orthogonally deprotected and tosylcarbamoylated on the side-chains of cysteine and serine, respectively. The donor scope included glucosyl as well as mannosyl trichloroacetimidates, carrying benzyl, acetyl, or isopropylidene protecting groups. Isopropylidene groups were found to be removed under the acidic conditions used for release of the neoglycopeptides from the solid support, yielding neoglycopeptides with unprotected hydroxyl groups. Glycosylation of a peptide containing a carbamoylated tyrosine was attempted as well, but the desired neoglycopeptide could not be synthesized due to thermal instability of the carbamate.
Original languageEnglish
Article numbere202400066
JournalChemPlusChem
Volume89
Issue number8
ISSN2192-6506
DOIs
Publication statusPublished - Aug 2024

Bibliographical note

Funding Information:
The authors are grateful for support from the Novo Nordisk Foundation via a NERD project grant (NNF22OC0076039), a biotechnology project grant (NNF18OC0034734) and for use of the Novo Nordisk Foundation NMR facility at the Department of Chemistry at Copenhagen University (NNF21OC0067315).

Keywords

  • glycosylation
  • N-glycosides
  • neoglycopeptides
  • self-promotion
  • solid-phase synthesis

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