Volume 57, Issue 51 pp. 16754-16759
Communication

Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation

Sainan Zhang

Sainan Zhang

State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071 China

College of Pharmacy, Nankai University, Tianjin, 300071 China

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Yunlong Zheng

Yunlong Zheng

State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071 China

College of Pharmacy, Nankai University, Tianjin, 300071 China

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Hongde An

Hongde An

State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071 China

College of Pharmacy, Nankai University, Tianjin, 300071 China

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Briana Aguila

Briana Aguila

Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, FL, 33620 USA

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Prof. Cheng-Xiong Yang

Prof. Cheng-Xiong Yang

College of Chemistry, Nankai University, Tianjin, 300071 China

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Yueyue Dong

Yueyue Dong

College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Wei Xie

Prof. Wei Xie

College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Peng Cheng

Prof. Peng Cheng

College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Zhenjie Zhang

Corresponding Author

Prof. Zhenjie Zhang

State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071 China

College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Yao Chen

Corresponding Author

Prof. Yao Chen

State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071 China

College of Pharmacy, Nankai University, Tianjin, 300071 China

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Prof. Shengqian Ma

Corresponding Author

Prof. Shengqian Ma

Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, FL, 33620 USA

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First published: 25 October 2018
Citations: 276

Graphical Abstract

COF chirality: A general and efficient strategy has been developed to introduce chirality into covalent organic frameworks (COFs) by covalently immobilizing biomolecules into achiral COFs. The biomolecules⊂COFs can serve as chiral stationary phases for efficient chiral separation of a broad range of racemates.

Abstract

The separation of racemic compounds is important in many fields, such as pharmacology and biology. Taking advantage of the intrinsically strong chiral environment and specific interactions featured by biomolecules, here we contribute a general strategy is developed to enrich chirality into covalent organic frameworks (COFs) by covalently immobilizing a series of biomolecules (amino acids, peptides, enzymes) into achiral COFs. Inheriting the strong chirality and specific interactions from the immobilized biomolecules, the afforded biomolecules⊂COFs serve as versatile and highly efficient chiral stationary phases towards various racemates in both normal and reverse phase of high-performance liquid chromatography (HPLC). The different interactions between enzyme secondary structure and racemates were revealed by surface-enhanced Raman scattering studies, accounting for the observed chiral separation capacity of enzymes⊂COFs.

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