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Dual-resolving of positional and geometric isomers of C=C bonds via bifunctional photocycloaddition-photoisomerization reaction system

Author

Listed:
  • Guifang Feng

    (The Institute for Advanced Studies, Wuhan University)

  • Ming Gao

    (The Institute for Advanced Studies, Wuhan University)

  • Liwei Wang

    (The Institute for Advanced Studies, Wuhan University)

  • Jiayi Chen

    (Union Hospital, Tongji Medical College, Huazhong University of Science and Technology)

  • Menglu Hou

    (The Institute for Advanced Studies, Wuhan University)

  • Qiongqiong Wan

    (The Institute for Advanced Studies, Wuhan University)

  • Yun Lin

    (Union Hospital, Tongji Medical College, Huazhong University of Science and Technology)

  • Guoyong Xu

    (The Institute for Advanced Studies, Wuhan University)

  • Xiaotian Qi

    (Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University)

  • Suming Chen

    (The Institute for Advanced Studies, Wuhan University)

Abstract

The biological functions of lipids largely depend on their chemical structures. The position and configuration of C=C bonds are two of the essential attributes that determine the structures of unsaturated lipids. However, simultaneous identification of both attributes remains challenging. Here, we develop a bifunctional visible-light-activated photocycloaddition-photoisomerization reaction system, which enables the dual-resolving of the positional and geometric isomerism of C=C bonds in lipids when combines with liquid chromatography-mass spectrometry. The dual-pathway reaction mechanism is demonstrated by experiments and density functional theory calculations. Based on this bifunctional reaction system, a workflow of deep structural lipidomics is established, and allows the revealing of unique patterns of cis-trans-isomers in bacteria, as well as the tracking of C=C positional isomers changes in mouse brain ischemia. This study not only offers a powerful tool for deep lipid structural biology, but also provides a paradigm for developing the multifunctional visible-light-induced reaction.

Suggested Citation

  • Guifang Feng & Ming Gao & Liwei Wang & Jiayi Chen & Menglu Hou & Qiongqiong Wan & Yun Lin & Guoyong Xu & Xiaotian Qi & Suming Chen, 2022. "Dual-resolving of positional and geometric isomers of C=C bonds via bifunctional photocycloaddition-photoisomerization reaction system," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30249-z
    DOI: 10.1038/s41467-022-30249-z
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    References listed on IDEAS

    as
    1. Wenpeng Zhang & Donghui Zhang & Qinhua Chen & Junhan Wu & Zheng Ouyang & Yu Xia, 2019. "Online photochemical derivatization enables comprehensive mass spectrometric analysis of unsaturated phospholipid isomers," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    2. Wenpeng Zhang & Donghui Zhang & Qinhua Chen & Junhan Wu & Zheng Ouyang & Yu Xia, 2019. "Publisher Correction: Online photochemical derivatization enables comprehensive mass spectrometric analysis of unsaturated phospholipid isomers," Nature Communications, Nature, vol. 10(1), pages 1-1, December.
    3. Wenbo Cao & Simin Cheng & Jing Yang & Jiaxin Feng & Wenpeng Zhang & Zishuai Li & Qinhua Chen & Yu Xia & Zheng Ouyang & Xiaoxiao Ma, 2020. "Large-scale lipid analysis with C=C location and sn-position isomer resolving power," Nature Communications, Nature, vol. 11(1), pages 1-11, December.
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    Cited by:

    1. Jan Philipp Menzel & Reuben S. E. Young & Aurélie H. Benfield & Julia S. Scott & Puttandon Wongsomboon & Lukáš Cudlman & Josef Cvačka & Lisa M. Butler & Sónia T. Henriques & Berwyck L. J. Poad & Steph, 2023. "Ozone-enabled fatty acid discovery reveals unexpected diversity in the human lipidome," Nature Communications, Nature, vol. 14(1), pages 1-16, December.

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