On-Resin Synthesis of Linear Aryl Thioether Containing Peptides and in-Solution Cyclization via Cysteine SNAr Reaction

作者：Li, Jian; Lai, Weihong; Pang, Ao; Liu, Lu; Ye, Lianbao^*; Xiong, Xiao-Feng^*

来源：Organic Letters, 2022, 24(8): 1673-1677.

DOI：10.1021/acs.orglett.2c00234

• MACROCYCLIZATION
• CHEMISTRY

Cyclic peptides represent one of the most promising therapeutic agents in drug discovery due to their good affinity and selectivity. Herein, an on-resin synthesis of aryl thioether containing peptides and a concise cyclization strategy via chemoselective cysteine SNAr reaction was developed. The arylation group could be incorporated into a series of amino acids and used for standard SPPS and peptides cyclization. Constructed cyclic peptides showed increased cellular uptakes compared to their linear peptides.

• 单位
  广东药学院; 中山大学