Enantioselective Diels-Alder reactions with left-handed G-quadruplex DNA-based catalysts

作     者：Kun Chen Zhiyong He Wei Xiong Chun-Jiang Wang Xiang Zhou Kun Chen;Zhiyong He;Wei Xiong;Chun-Jiang Wang;Xiang Zhou

作者机构：College of Chemistry and Molecular SciencesKey Laboratory of Biomedical Polymers of Ministry of EducationWuhan UniversityWuhan 430072China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2021年第32卷第5期

页      面：1701-1704页

核心收录：

学科分类：07[理学] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：This work was supported by the National Natural Science Foundation of China(Nos.21432008 91753201 and 21721005). 

主　　题：Diels-Alder reaction Left-handed G-quadruplex Asymmetric catalysis Enantioselectiv ity G-quadruplex ligand 

摘      要：Since the discovery of left-handed G-quadruplex(L-G4)structure formed by natural DNA,there has been a growing interest in its potential functions.This study utilised it to catalyse enantioselective Diels-Alder reactions,considering its different optical rotation compared to an ordinary G4.It was determined that when L-G4 was used with a combination of copper(Ⅱ)ions,there was a good enantioselectivity(-52%ee)without further addition of ligands.When further consideration was given by adding G4 ligands,G4 was further stabilised,even obtaining a better enantioselectivity(up to-80%ee).Moreover,when using ligands that have regulatory effects on G4,the ee value can be adjusted.In this work,a minimal left-handed G4 was reported.A follow-up study was also con ducted,which recovers that the minimal left-handed G4 remains its catalytic effect and enantioselectivity,but is not so effective as the former case.This indicates that a complete G4 structure is relatively conducive to chiral catalysis.