Nature-Inspired Bioorthogonal Reaction: Development of β-Caryophyllene as a Chemical Reporter in Tetrazine Ligation
- Yunfei Wu
Yunfei WuSchool of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaCollaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Medical School, Sichuan University, Chengdu 610041, ChinaMore by Yunfei Wu
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- Jiulong Hu
Jiulong HuSchool of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaState Key Laboratory of Membrane Biology, School of Life Sciences, Tsinghua University, Beijing 100084, ChinaMore by Jiulong Hu
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- Chen Sun
Chen SunState Key Laboratory of Membrane Biology, School of Life Sciences, Tsinghua University, Beijing 100084, ChinaMore by Chen Sun
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- Yu Cao
Yu CaoState Key Laboratory of Membrane Biology, School of Life Sciences, Tsinghua University, Beijing 100084, ChinaMore by Yu Cao
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- Yuanhe Li
Yuanhe LiSchool of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaMore by Yuanhe Li
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- Fayang Xie
Fayang XieSchool of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaMore by Fayang Xie
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- Tianyin Zeng
Tianyin ZengSchool of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaMore by Tianyin Zeng
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- Bing Zhou*
Bing Zhou*E-mail: [email protected]State Key Laboratory of Membrane Biology, School of Life Sciences, Tsinghua University, Beijing 100084, ChinaMore by Bing Zhou
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- Juanjuan Du*
Juanjuan Du*E-mail: [email protected]School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaMore by Juanjuan Du
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- Yefeng Tang*
Yefeng Tang*E-mail: [email protected]School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, ChinaCollaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Medical School, Sichuan University, Chengdu 610041, ChinaMore by Yefeng Tang
Abstract
A nature-inspired bioorthogonal reaction has been developed, hinging on an inverse-electron-demand Diels–Alder reaction of tetrazine with β-caryophyllene. Readily accessible from the cheap starting material through a scalable synthesis, the newly developed β-caryophyllene chemical reporter displays appealing reaction kinetics and excellent biocompatibility, which renders it applicable to both in vitro protein labeling and live cell imaging. Moreover, it can be used orthogonally to the strain-promoted alkyne–azide cycloaddition for dual protein labeling. This work not only provides an alternative to the existing bioorthogonal reaction toolbox, but also opens a new avenue to utilize naturally occurring scaffolds as bioorthogonal chemical reporters.
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This article is cited by 10 publications.
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- Yulia V. Gyrdymova, Svetlana A. Rubtsova. Caryophyllene and caryophyllene oxide: a variety of chemical transformations and biological activities. Chemical Papers 2022, 76 (1) , 1-39. https://doi.org/10.1007/s11696-021-01865-8
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