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Chemoselective Glycosylation of Peptides through S‐Alkylation Reaction
Author(s) -
Calce Enrica,
Digilio Giuseppe,
Menchise Valeria,
Saviano Michele,
De Luca Stefania
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800265
Subject(s) - glycosyl , chemistry , alkylation , glycosylation , electrophile , stereoselectivity , peptide , glycopeptide , combinatorial chemistry , yield (engineering) , cysteine , disaccharide , glycosyl donor , glycan , leaving group , stereochemistry , organic chemistry , biochemistry , catalysis , glycoprotein , materials science , antibiotics , metallurgy , enzyme
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.