Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase.
Chempluschem
; 89(8): e202400066, 2024 Aug.
Article
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| MEDLINE
| ID: mdl-38523065
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.
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Banco de datos:
MEDLINE
Asunto principal:
Péptidos
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En
Revista:
Chempluschem
Año:
2024
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Article
País de afiliación:
Dinamarca