Chemoselective elaboration of O-linked glycopeptide mimetics by alkylation of 3-thioGalNAc

LA Marcaurelle, CR Bertozzi

文献索引：Marcaurelle; Bertozzi Journal of the American Chemical Society, 2001 , vol. 123, # 8 p. 1587 - 1595

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被引用次数: 67

摘要

A critical branch point in mucin-type oligosaccharides is the β1→ 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. The key building block was a 2-azido-3- thiogalactose-Thr analogue that was incorporated into a peptide by ...