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

Guifang Feng, Ming Gao, Liwei Wang, Jiayi Chen, Menglu Hou, Qiongqiong Wan, Yun Lin, Guoyong Xu, Xiaotian Qi and Suming Chen ()
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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

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-30249-z

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