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Chemical Synthesis Of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation And Chemoselective Solid-Phase Aspartylation, Chen Zeng, Bin Sun, Xuefeng Cao, Joshua Zhu, Olawale Micheal Oluwadahunsi, Ding Liu, He Zhu, Jiabin Zhang, Qing Zhang, Gaolan Zhang, Christopher Andrew Gibbons, Yunpeng Liu, Jun Zhou, Peng George Wang

Faculty Work Comprehensive List

We report herein an efficient chemical synthesis of homogeneous human E-cadherin N-linked glycopeptides consisting of a heptapeptide sequence adjacent to the Asn-633 N-glycosylation site with representative N-glycan structures, including a conserved trisaccharide, a core-fucosylated tetrasaccharide, and a complex-type biantennary octasaccharide. The key steps are a chemoselective on-resin aspartylation using a pseudoproline-containing peptide and stereoselective glycosylation using glycosyl fluororide as a donor. This synthetic strategy demonstrates potential utility in accessing a wide range of homogeneous N-linked glycopeptides for the examination of their biological function.