Precise Recognition in Water by an Endo-Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang, Yan-Fang1; Wang, Song-Meng1; Zhang, Xiaobin3; Nian, Hao1; Zheng, Li-Shuo1; Wang, Xiaoping1; Schreckenbach, Georg3; Jiang, Wei1; Yang, Liu-Pan2; Wang, Li-Li2

2023-10-01

10.1002/anie.202310115

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Precise binding towards structurally similar substrates is a common feature of biomolecular recognition. However, achieving such selectivity-especially in distinguishing subtle differences in substrates-with synthetic hosts can be quite challenging. Herein, we report a novel design strategy involving the combination of different rigid skeletons to adjust the distance between recognition sites within the cavity, which allows for the highly selective recognition of hydrogen-bonding complementary substrates, such as 4-chromanone. X-ray single-crystal structures and density functional theory calculations confirmed that the distance of endo-functionalized groups within the rigid cavity is crucial for achieving high binding selectivity through hydrogen bonding. The thermodynamic data and molecular dynamics simulations revealed a significant influence of the hydrophobic cavity on the binding affinity. The new receptor possesses both high selectivity and high affinity, which provide valuable insights for the design of customized receptors.

Hydrogen Bonding Rigid Scaffolds Selective Recognition Synthetic Receptors

SCI ; EI

英语

NI论文

第一

In memory of Wei Jiang (deceased, 2022.12). This research was financially supported by the National Natural Science Foundation of China (22174059), and the Department of Education of Guangdong Province (2020ZDZX2060). We are grateful to the technical suppo[2022.12] ; National Natural Science Foundation of China[22174059] ; Department of Education of Guangdong Province[2020ZDZX2060]

Chemistry

Chemistry, Multidisciplinary

WOS:001085599900001

WILEY-V C H VERLAG GMBH

20234314928450

Binding energy ; Binding sites ; Density functional theory ; Hydrogen ; Hydrophobicity ; Molecular dynamics ; Scaffolds ; Single crystals

Construction Equipment:405.1 ; Biochemistry:801.2 ; Physical Chemistry:801.4 ; Chemical Products Generally:804 ; Probability Theory:922.1 ; Physical Properties of Gases, Liquids and Solids:931.2 ; Atomic and Molecular Physics:931.3 ; Quantum Theory; Quantum Mechanics:931.4 ; Crystalline Solids:933.1

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China
2.Univ South China, Sch Pharmaceut Sci, Hengyang Med Sch, Hengyang 421001, Hunan, Peoples R China
3.Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada

Wang, Yan-Fang,Wang, Song-Meng,Zhang, Xiaobin,et al. Precise Recognition in Water by an Endo-Functionalized Cavity: Tuning the Complementarity of Binding Sites[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62.

Wang, Yan-Fang.,Wang, Song-Meng.,Zhang, Xiaobin.,Nian, Hao.,Zheng, Li-Shuo.,...&Wang, Li-Li.(2023).Precise Recognition in Water by an Endo-Functionalized Cavity: Tuning the Complementarity of Binding Sites.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62.

Wang, Yan-Fang,et al."Precise Recognition in Water by an Endo-Functionalized Cavity: Tuning the Complementarity of Binding Sites".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62(2023).