Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation

Zeng, Chen1; Sun, Bin1; Cao, Xuefeng2; Zhu, Hailiang2; Oluwadahunsi, Olawale Micheal2; Liu, Ding2; Zhu, He2; Zhang, Jiabin2; Zhang, Qing2; Zhang, Gaolan2; Gibbons, Christopher Andrew2; Liu, Yunpeng2; Zhou, Jun2,3; Wang, Peng George1,2

2020-11-06

10.1021/acs.orglett.0c02971

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

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.

SCI

英语

NI期刊 ; NI论文

第一 ; 通讯

Chemistry

Chemistry, Organic

WOS:000589942900032

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Sch Med, Shenzhen 518055, Peoples R China
2.Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA
3.WuXi AppTec, R&D Headquarters, Shanghai 200131, Peoples R China

Zeng, Chen,Sun, Bin,Cao, Xuefeng,et al. Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation[J]. ORGANIC LETTERS,2020,22(21).

Zeng, Chen.,Sun, Bin.,Cao, Xuefeng.,Zhu, Hailiang.,Oluwadahunsi, Olawale Micheal.,...&Wang, Peng George.(2020).Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation.ORGANIC LETTERS,22(21).

Zeng, Chen,et al."Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation".ORGANIC LETTERS 22.21(2020).