Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase
Research output: Contribution to journal › Journal article › Research › peer-review
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 language | English |
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Article number | e202400066 |
Journal | ChemPlusChem |
ISSN | 2192-6506 |
DOIs | |
Publication status | Accepted/In press - 2024 |
Bibliographical note
Publisher Copyright:
© 2024 The Authors. ChemPlusChem published by Wiley-VCH GmbH.
- glycosylation, N-glycosides, neoglycopeptides, self-promotion, solid-phase synthesis
Research areas
ID: 389416935