Citation: Kun Chen, Zhiyong He, Wei Xiong, Chun-Jiang Wang, Xiang Zhou. Enantioselective Diels–Alder reactions with left-handed G-quadruplex DNA-based catalysts[J]. Chinese Chemical Letters, ;2021, 32(5): 1701-1704. doi: 10.1016/j.cclet.2020.12.047 shu

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

College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China

xzhou@whu.edu.cn

Received Date: 4 November 2020
Revised Date: 21 December 2020
Accepted Date: 23 December 2020
Available Online: 29 December 2020

Figures(2)

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 conducted, 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.
- Diels–Alder reaction,
- Left-handed G-quadruplex,
- Asymmetric catalysis,
- Enantioselectivity,
- G-quadruplex ligand
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