Chemoselective Glycosylation of Peptides through S-Alkylation Reaction

Enrica Calce, Giuseppe Digilio, Valeria Menchise, Michele Saviano, Stefania De Luca

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

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 originaleInglese
pagine (da-a)6231-6238
Numero di pagine8
RivistaChemistry - A European Journal
Volume24
Numero di pubblicazione23
DOI
Stato di pubblicazionePubblicato - 20 apr 2018

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