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An Efficient Cyclic Di‐AMP Based Artificial Metalloribozyme for Enantioselective Diels–Alder Reactions
Author(s) -
Qi Qianqian,
Lv Shuting,
Hao Min,
Dong Xingchen,
Gu Youkun,
Wu Peizhe,
Zhang Wenyue,
Chen Yashao,
Wang Changhao
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000652
Subject(s) - enantioselective synthesis , chemistry , catalysis , nucleic acid , rna , cofactor , diels–alder reaction , combinatorial chemistry , stereochemistry , organic chemistry , enzyme , biochemistry , gene
The diverse structures of nucleic acids as scaffolds have brought the significant advancement for DNA‐based enantioselective catalysis, yet RNA‐based enantioselective catalysis is lacking investigation. Herein, we report a small, natural RNA of cyclic di‐AMP (c‐di‐AMP) and Cu 2+ ions assemble into an artificial metalloribozyme (c‐di‐AMP · Cu 2+ ), that could effectively catalyze the enantioselective Diels–Alder reactions with up to 80 % ee . The enantioselective catalytic performance of c‐di‐AMP · Cu 2+ has been studied by thorough investigations of different metal cofactors, c‐di‐AMP/Cu 2+ molar ratios, additives, buffers and c‐di‐AMP analogues. In addition, the assembly of c‐di‐AMP · Cu 2+ gives rise to 300‐fold and 5‐fold rate acceleration compared to the uncatalyzed reaction and Cu 2+ ions, respectively. This work provides a simple and efficient strategy to construct the RNA‐based catalysts that would expand the current nucleic acids‐based catalysis and might hint the possible catalytic RNA in primordial chemistry.