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

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

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WANG, Changhao, Qianqian QI, Wenying LI, Jingshuang DANG, Min HAO, Shuting LV, Xingchen DONG, Youkun GU, Peizhe WU, Jörg S. HARTIG, 2020. A Cu(II)-ATP complex efficiently catalyses enantioselective Diels-Alder reactions. In: Nature Communications. Nature Publishing Group. 11, 4792. eISSN 2041-1723. Available under: doi: 10.1038/s41467-020-18554-x

@article{Wang2020CuIIA-52066, title={A Cu(II)-ATP complex efficiently catalyses enantioselective Diels-Alder reactions}, year={2020}, doi={10.1038/s41467-020-18554-x}, volume={11}, journal={Nature Communications}, author={Wang, Changhao and Qi, Qianqian and Li, Wenying and Dang, Jingshuang and Hao, Min and Lv, Shuting and Dong, Xingchen and Gu, Youkun and Wu, Peizhe and Hartig, Jörg S.}, note={Article Number: 4792} }

Qi, Qianqian Dong, Xingchen Lv, Shuting Li, Wenying A Cu(II)-ATP complex efficiently catalyses enantioselective Diels-Alder reactions Dang, Jingshuang 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 (Cu<sup>2+</sup>·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. Gu, Youkun Wang, Changhao Dong, Xingchen Wu, Peizhe eng Qi, Qianqian Hartig, Jörg S. Hao, Min Dang, Jingshuang Wu, Peizhe Li, Wenying Wang, Changhao Gu, Youkun Hartig, Jörg S. Lv, Shuting Hao, Min 2020-12-09T13:54:16Z 2020 2020-12-09T13:54:16Z Attribution 4.0 International

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