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Chiral substrate-induced chiral covalent organic framework membranes for enantioselective separation of macromolecular drug

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  • Xiaoyue Gao

    (Jilin University)

  • Teng Ben

    (Jilin University
    Zhejiang Normal University
    Zhejiang Normal University)

Abstract

Chiral drugs are essential in modern medicine, but separating their enantiomers is challenging due to their similar physicochemical properties. However, traditional methods are often costly and inefficient. Here we show that chiral covalent organic framework (CCOF-300) membranes, induced by chiral dopants (L-( + )-/D-(–)-tartaric acid), can achieve high enantioselectivity in separating chiral drugs. Specifically, CCOF-300 membrane achieved 100% enantiomeric excess in separating racemic N-Fmoc-N’-[1-(4,4-Dimethyl–2,6-dioxocyclohexylidene)ethyl]-lysine (Fmoc-Lys(Dde)-OH). We found that size matching and differences in diffusion rates between enantiomers are key factors in chiral separation. Additionally, there were no significant differences in the binding energy between ibuprofen (IBU), Fmoc-Lys(Dde)-OH, and CCOF-300, indicating that binding energy is not the dominant factor in chiral separation. This study proposes a cost-effective and scalable method for chiral drug separation, highlighting the potential of chiral induction strategy in improving chiral separation technology in the pharmaceutical industry.

Suggested Citation

  • Xiaoyue Gao & Teng Ben, 2025. "Chiral substrate-induced chiral covalent organic framework membranes for enantioselective separation of macromolecular drug," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-60572-0
    DOI: 10.1038/s41467-025-60572-0
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    References listed on IDEAS

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    1. Xing Han & Jie Zhang & Jinjing Huang & Xiaowei Wu & Daqiang Yuan & Yan Liu & Yong Cui, 2018. "Chiral induction in covalent organic frameworks," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
    2. Hang Wang & Shuang Zhao & Yi Liu & Ruxin Yao & Xiaoqi Wang & Yuhua Cao & Dou Ma & Mingchu Zou & Anyuan Cao & Xiao Feng & Bo Wang, 2019. "Membrane adsorbers with ultrahigh metal-organic framework loading for high flux separations," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    3. Zongsu Han & Kunyu Wang & Yifan Guo & Wenjie Chen & Jiale Zhang & Xinran Zhang & Giuliano Siligardi & Sihai Yang & Zhen Zhou & Pingchuan Sun & Wei Shi & Peng Cheng, 2019. "Cation-induced chirality in a bifunctional metal-organic framework for quantitative enantioselective recognition," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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