anions, peptides and proteins, monomers, free radicals, post-translational modification
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.
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American Chemical Society
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Zeng, C., Sun, B., Cao, X., Zhu, J., Oluwadahunsi, O. M., Liu, D., Zhu, H., Zhang, J., Zhang, Q., Zhang, G., Gibbons, C. A., Liu, Y., Zhou, J., & Wang, P. G. (2020). Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation. Organic Letters, 22 (21), 8349. https://doi.org/10.1021/acs.orglett.0c02971