Photoinduced Addition of Glycosyl Thiols to Alkynyl Peptides: Use of Free-Radical Thiol−Yne Coupling for Post-Translational Double-Glycosylation of Peptides

作者：Mauro Lo Conte, Salvatore Pacifico, Angela Chambery, Alberto Marra, Alessandro Dondoni · 发表于：The Journal of Organic Chemistry · 年份：2010 · DOI：10.1021/jo1008178 · 被引用次数：97 · 研究领域：Click Chemistry and Applications、Chemical Synthesis and Analysis、Carbohydrate Chemistry and Synthesis

Double glycosylation of cysteine-containing peptides has been carried out by a one-pot two-step sequence comprising selective S-propargylation followed by photoinduced (lambda (max) 365 nm) free-radical hydrothiolation with glycosyl thiols. Conditions were established for the sequential introduction of two different thiol residues such as a glycosyl and a biotinyl derivative.