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Chiral covalent organic framework-monolith as stationary phase for high-performance liquid chromatographic enantioseparation of selected amino acids

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Abstract

The separation of amino acid (AA) enantiomers shows significance for chemistry, food, and biology, but remains challenging due to their similar properties. A promising nanoporous chiral covalent organic framework (COF) as a stationary phase for high-performance liquid chromatography (HPLC) suffers from the irregularity and widely distributed particle size of the chiral COF. Herein, we show the facile preparation of a chiral COF-monolith as a stationary phase for HPLC enantiomeric separation of AAs via orthogonal experiments. The CTzDa-monolith is prepared by the incorporation of the model chiral COF named CTzDa into the porous poly(ethylene dimethacrylate-co-methacrylate) monolith and reveals great permeability and mechanical stability. The corresponding CTzDa-monolithic column gives better chiral HPLC separation of AAs than the commercial Poroshell 120 chiral-T column. Thermal dynamic analysis and molecular docking calculations imply the involvement of stereoscopic hydrogen, π-π, and van der Waals interactions between the CTzDa and AAs during HPLC enantioseparation. The facile incorporation of the chiral COF into the porous monolith will promote the potential of a chiral COF as a stationary phase for HPLC.

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Funding

The authors are grateful for the support from the National Natural Science Foundation of China (No. 21804055, 21775056, 22076066), the Natural Science Foundation of Jiangsu Province (No. BK20180585), the Fundamental Research Funds for the Central Universities (No. JUSRP221002), the National First-class Discipline Program of Food Science and Technology (No. JUFSTR20180301), and the Program of “Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province.”

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Authors and Affiliations

  1. Institute of Analytical Food Safety, School of Food Science and Technology, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Hai-Long Qian, Fang Liu, Xue Liu & Xiu-Ping Yan

  2. State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Cheng Yang & Xiu-Ping Yan

  3. Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Xiu-Ping Yan

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  1. Hai-Long Qian
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  2. Fang Liu
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  4. Cheng Yang
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Correspondence to Hai-Long Qian.

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Published in the topical collection featuring Promising Early-Career (Bio)Analytical Researchers with guest editors Antje J. Baeumner, María C. Moreno-Bondi, Sabine Szunerits, and Qiuquan Wang.

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Qian, HL., Liu, F., Liu, X. et al. Chiral covalent organic framework-monolith as stationary phase for high-performance liquid chromatographic enantioseparation of selected amino acids. Anal Bioanal Chem 414, 5255–5262 (2022). https://doi.org/10.1007/s00216-021-03574-3

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  • DOI: https://doi.org/10.1007/s00216-021-03574-3

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