A Cu(II)–ATP complex efficiently catalyses enantioselective Diels–Alder reactions

Changhao Wang (), Qianqian Qi, Wenying Li, Jingshuang Dang, Min Hao, Shuting Lv, Xingchen Dong, Youkun Gu, Peizhe Wu, Wenyue Zhang, Yashao Chen and Jörg S. Hartig
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Changhao Wang: Shaanxi Normal University
Qianqian Qi: Shaanxi Normal University
Wenying Li: Shaanxi Normal University
Jingshuang Dang: Shaanxi Normal University
Min Hao: Shaanxi Normal University
Shuting Lv: Shaanxi Normal University
Xingchen Dong: Shaanxi Normal University
Youkun Gu: Shaanxi Normal University
Peizhe Wu: Shaanxi Normal University
Wenyue Zhang: Shaanxi Normal University
Yashao Chen: Shaanxi Normal University
Jörg S. Hartig: University of Konstanz

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Natural biomolecules have been used extensively as chiral scaffolds that bind/surround metal complexes to achieve stereoselectivity in catalytic reactions. ATP is ubiquitously found in nature as an energy-storing molecule and can complex diverse metal cations. However, in biotic reactions ATP-metal complexes are thought to function mostly as co-substrates undergoing phosphoanhydride bond cleavage reactions rather than participating in catalytic mechanisms. Here, we report that a specific Cu(II)-ATP complex (Cu2+·ATP) efficiently catalyses Diels-Alder reactions with high reactivity and enantioselectivity. We investigate the substrates and stereoselectivity of the reaction, characterise the catalyst by a range of physicochemical experiments and propose the reaction mechanism based on density functional theory (DFT) calculations. It is found that three key residues (N7, β-phosphate and γ-phosphate) in ATP are important for the efficient catalytic activity and stereocontrol via complexation of the Cu(II) ion. In addition to the potential technological uses, these findings could have general implications for the chemical selection of complex mixtures in prebiotic scenarios.

Date: 2020
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DOI: 10.1038/s41467-020-18554-x

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