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Chiral chemicals have attracted significant interest in the pharmaceutical industry, yet the separation methods to get pure enantiomers from racemic mixture are still challenging. To date, the separation of enantiomers still mainly depends on chromatography using high-cost chiral stationary phases. Herein, wood channels were used as the handheld integrated device, and enantiomer separation was simultaneously detected using an electrochemical detector. In this method, a chiral UIO-66 (L-UIO-66) modified enantiomer separation zone and carbonized wood based online detection zone are integrated along a single wood column. Based on the in situ separation results from the chronoamperometry data, the wood device shows excellent separation ability for a wide range of electrochemically active enantiomers, including 3,4-dihydroxyphenylalanine, amino acids, ascorbic acid, carnitine, and penicillamine with high chirality purity. The unbiased molecular dynamic simulations indicate that the excellent chiral recognition and separation are attributed to the different barriers from the bound states to the dissociated state of the enantiomers in the homochiral microenvironment of the framework. This integrated enantiomer separation-electrochemical detection device provides a novel, easy, and low-cost platform for the separation of pure enantiomer from racemic mixture.


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Integrated separation-electrochemical detection device based on wood column for online identification of enantiomer

Show Author's information Junli Guo1,§Yuanfei Xue2,3,4,§Chenxi Zhao1Junjian Zhao1Zhida Gao1Ye Mei2,3,4( )Yan-Yan Song1( )
College of Sciences, Northeastern University, Shenyang 110004, China
State Key Laboratory of Precision Spectroscopy, School of Physics and Electronic Science, East China Normal University, Shanghai 200062, China
NYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai 200062, China
Collaborative Innovation Center of Extreme Optics, Shanxi University, Taiyuan 030006, China

§ Junli Guo and Yuanfei Xue contributed equally to this work.

Abstract

Chiral chemicals have attracted significant interest in the pharmaceutical industry, yet the separation methods to get pure enantiomers from racemic mixture are still challenging. To date, the separation of enantiomers still mainly depends on chromatography using high-cost chiral stationary phases. Herein, wood channels were used as the handheld integrated device, and enantiomer separation was simultaneously detected using an electrochemical detector. In this method, a chiral UIO-66 (L-UIO-66) modified enantiomer separation zone and carbonized wood based online detection zone are integrated along a single wood column. Based on the in situ separation results from the chronoamperometry data, the wood device shows excellent separation ability for a wide range of electrochemically active enantiomers, including 3,4-dihydroxyphenylalanine, amino acids, ascorbic acid, carnitine, and penicillamine with high chirality purity. The unbiased molecular dynamic simulations indicate that the excellent chiral recognition and separation are attributed to the different barriers from the bound states to the dissociated state of the enantiomers in the homochiral microenvironment of the framework. This integrated enantiomer separation-electrochemical detection device provides a novel, easy, and low-cost platform for the separation of pure enantiomer from racemic mixture.

Keywords: enantioselectivity, wood column, online sensing, integrated separation-detection device, free energy barrier

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Publication history
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Acknowledgements

Publication history

Received: 22 May 2023
Revised: 03 July 2023
Accepted: 10 July 2023
Published: 24 August 2023
Issue date: March 2024

Copyright

© Tsinghua University Press 2023

Acknowledgements

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 22074013 and 22073030). The CPU time was supported by the Supercomputer Centre of East China Normal University (ECNU Public Platform for Innovation No. 001). Special thanks are due to the instrumental or data analysis from Analytical and Testing Center, Northeastern University.

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