Biomimetic Recognition of Quinones in Water by an Endo-Functionalized Cavity with Anthracene Sidewalls

Zhou, Hang1,2; Pang, Xin-Yu1,2; Wang, Xiaoping1,2; Yao, Huan1,2; Yang, Liu-Pan1,2; Jiang, Wei1,2

2021-11-01

10.1002/anie.202112267

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Selective molecular recognition in water is the foundation of numerous biological functions but is a challenge for most synthetic hosts. We employ the concept of endo-functionalized cavity and the strategy of simultaneous construction to address this issue. The concept and the strategy were demonstrated in the construction of a biomimetic host for selectively recognizing quinones in water. The host was synthesized by joining two pieces of bent anthracene dimer through amide bond formation, affording a deep hydrophobic cavity and inward-directing hydrogen bonding sites. The host can recognize quinones over their close analogues in water, and its association affinity to p-benzoquinone is the highest among all the known hosts and is even comparable to that of the bioreceptor. The binding with an anthraquinone reaches nanomolar affinity. Shielded hydrogen bonding, C-H...pi, and charge transfer interactions, and the hydrophobic effect are responsible for the high binding affinity and selectivity.

biomimetic molecular recognition endo-functionalized cavity quinones simultaneous construction

SCI ; EI

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21772083,21822104,22125105] ; Shenzhen Science and Technology Innovation Committee[JCYJ20180504165810828] ; Guangdong High-Level Personnel of Special Support Program[2019TX05C157] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000713757700001

WILEY-V C H VERLAG GMBH

20214511108436

Amides ; Anthracene ; Binding energy ; Biomimetics ; Charge transfer ; Dimers ; Hydrogen ; Hydrophobicity ; Ketones ; Molecular recognition ; Quinone

Biotechnology:461.8 ; Biology:461.9 ; Energy Storage:525.7 ; Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Organic Polymers:815.1.1 ; Physical Properties of Gases, Liquids and Solids:931.2

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China

Zhou, Hang,Pang, Xin-Yu,Wang, Xiaoping,et al. Biomimetic Recognition of Quinones in Water by an Endo-Functionalized Cavity with Anthracene Sidewalls[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60:25981-25987.

Zhou, Hang,Pang, Xin-Yu,Wang, Xiaoping,Yao, Huan,Yang, Liu-Pan,&Jiang, Wei.(2021).Biomimetic Recognition of Quinones in Water by an Endo-Functionalized Cavity with Anthracene Sidewalls.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60,25981-25987.

Zhou, Hang,et al."Biomimetic Recognition of Quinones in Water by an Endo-Functionalized Cavity with Anthracene Sidewalls".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60(2021):25981-25987.