Institute of Biostructures and Bioimaging, National Research Council, 80134, Naples, Italy.
Department of Science and Technologic Innovation, Università del Piemonte Orientale "A. Avogadro", 15121, Alessandria, Italy.
Chemistry. 2018 Apr 20;24(23):6231-6238. doi: 10.1002/chem.201800265. Epub 2018 Apr 14.
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.
本文报道了一种高效、快速合成 S-连接糖肽的方法。该方法使用活化分子筛作为碱，促进适当的糖基卤化物与易于制备的含半胱氨酸肽反应，选择性地进行 S-烷基化。考虑到所采用的非常温和的条件，亲电糖与肽巯基基团的化学选择性连接以令人满意的产率发生，允许单糖和二糖部分的掺入。从α-D-糖基衍生物获得的糖肽缀合物采用β-S-构型，表明取代反应具有高立体选择性。
