Abstract
An efficient and rapid procedure for synthesizing S-linked glycopeptides is reported. The approach uses activated molecular sieves as a base to promote the selective S-alkylation of readily prepared cysteine-containing peptides, upon reaction of appropriate glycosyl halides. Considering the very mild conditions employed, the chemoselective linkage of the electrophilic sugar with a peptide sulfhydryl group occurred in satisfactory yield, allowing the incorporation of mono and disaccharide moieties. The sugar–peptide conjugates obtained from α-d-glycosyl derivatives adopt a β-S-configuration, indicating the high stereoselectivity of the substitution reaction.
Lingua originale | Inglese |
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pagine (da-a) | 6231-6238 |
Numero di pagine | 8 |
Rivista | Chemistry - A European Journal |
Volume | 24 |
Numero di pubblicazione | 23 |
DOI | |
Stato di pubblicazione | Pubblicato - 20 apr 2018 |