Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel‐Crafts Reactions in Water

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2020
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Hao, Min
Qi, Qianqian
Dang, Jingshuang
Dong, Xingchen
Lv, Shuting
Xiong, Ling
Gao, Huanhuan
Chen, Yashao
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The diverse secondary structures of nucleic acids are emerging as attractive chiral scaffolds to construct artificial metalloenzymes (ArMs) for enantioselective catalysis. DNA-based ArMs containing duplex and G-quadruplex scaffolds have been widely investigated, yet RNA-based ArMs are scarce. Here we report that a cyclic dinucleotide of c-di-AMP and Cu2+ ions assemble into an artificial metalloribozyme (c-di-AMP⋅Cu2+ ) that enables catalysis of enantioselective Friedel-Crafts reactions in aqueous media with high reactivity and excellent enantioselectivity of up to 97 % ee. The assembly of c-di-AMP⋅Cu2+ gives rise to a 20-fold rate acceleration compared to Cu2+ ions. Based on various biophysical techniques and density function theory (DFT) calculations, a fine coordination structure of c-di-AMP⋅Cu2+ metalloribozyme is suggested in which two c-di-AMP form a dimer scaffold and the Cu2+ ion is located in the center of an adenine-adenine plane through binding to two N7 nitrogen atoms and one phosphate oxygen atom.

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ISO 690WANG, Changhao, Min HAO, Qianqian QI, Jingshuang DANG, Xingchen DONG, Shuting LV, Ling XIONG, Huanhuan GAO, Yashao CHEN, Jörg S. HARTIG, 2020. Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel‐Crafts Reactions in Water. In: Angewandte Chemie International Edition. Wiley. 2020, 59(9), pp. 3444-3449. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201912962
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@article{Wang2020-02-24Highl-48222,
  year={2020},
  doi={10.1002/anie.201912962},
  title={Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel‐Crafts Reactions in Water},
  number={9},
  volume={59},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={3444--3449},
  author={Wang, Changhao and Hao, Min and Qi, Qianqian and Dang, Jingshuang and Dong, Xingchen and Lv, Shuting and Xiong, Ling and Gao, Huanhuan and Chen, Yashao and Hartig, Jörg S.}
}
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