2H‑Azirine-Based Reagents for Chemoselective Bioconjugation at Carboxyl Residues Inside Live Cells
Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues. It is thus desirable to develop novel methods that can covalently modify other res...
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| Published in | Journal of the American Chemical Society Vol. 142; no. 13; pp. 6051 - 6059 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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01.04.2020
Amer Chemical Soc |
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| Abstract | Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues. It is thus desirable to develop novel methods that can covalently modify other residues. Despite the fact that the carboxyl residues are crucial for maintaining the protein function, few selective labeling reactions are currently available. Here, we describe a novel reactive probe, 3-phenyl-2H-azirine, that enables chemoselective modification of carboxyl groups in proteins under both in vitro and in situ conditions with excellent efficiency. Furthermore, proteome-wide profiling of reactive carboxyl residues was performed with a quantitative chemoproteomic platform. |
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| AbstractList | Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues. It is thus desirable to develop novel methods that can covalently modify other residues. Despite the fact that the carboxyl residues are crucial for maintaining the protein function, few selective labeling reactions are currently available. Here, we describe a novel reactive probe, 3-phenyl-2H-azirine, that enables chemoselective modification of carboxyl groups in proteins under both in vitro and in situ conditions with excellent efficiency. Furthermore, proteome-wide profiling of reactive carboxyl residues was performed with a quantitative chemoproteomic platform. Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues. It is thus desirable to develop novel methods that can covalently modify other residues. Despite the fact that the carboxyl residues are crucial for maintaining the protein function, few selective labeling reactions are currently available. Here, we describe a novel reactive probe, 3-phenyl-2H-azirine, that enables chemoselective modification of carboxyl groups in proteins under both in vitro and in situ conditions with excellent efficiency. Furthermore, proteome-wide profiling of reactive carboxyl residues was performed with a quantitative chemoproteomic platform.Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues. It is thus desirable to develop novel methods that can covalently modify other residues. Despite the fact that the carboxyl residues are crucial for maintaining the protein function, few selective labeling reactions are currently available. Here, we describe a novel reactive probe, 3-phenyl-2H-azirine, that enables chemoselective modification of carboxyl groups in proteins under both in vitro and in situ conditions with excellent efficiency. Furthermore, proteome-wide profiling of reactive carboxyl residues was performed with a quantitative chemoproteomic platform. |
| Author | Ye, Wencai Hu, Jun Huang, Minhao Ma, Nan Zhang, Zhi-Min Yin, Xingfeng Liu, Wenyan Fan, Youlong Wang, Jigang Ding, Ke Li, Zhengqiu |
| AuthorAffiliation | Jinan University Artemisinin Research Center and Institute of Chinese Materia Medica International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China Shenzhen People’s Hospital China Academy of Chinese Medical Sciences Institute of Life and Health Engineering, College of Life Science and Technology The Second Clinical Medical College of Jinan University |
| AuthorAffiliation_xml | – name: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – name: Jinan University – name: Institute of Life and Health Engineering, College of Life Science and Technology – name: The Second Clinical Medical College of Jinan University – name: Artemisinin Research Center and Institute of Chinese Materia Medica – name: Shenzhen People’s Hospital – name: China Academy of Chinese Medical Sciences |
| Author_xml | – sequence: 1 givenname: Nan orcidid: 0000-0002-8518-5627 surname: Ma fullname: Ma, Nan organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 2 givenname: Jun surname: Hu fullname: Hu, Jun organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 3 givenname: Zhi-Min surname: Zhang fullname: Zhang, Zhi-Min organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 4 givenname: Wenyan surname: Liu fullname: Liu, Wenyan organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 5 givenname: Minhao surname: Huang fullname: Huang, Minhao organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 6 givenname: Youlong surname: Fan fullname: Fan, Youlong organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 7 givenname: Xingfeng surname: Yin fullname: Yin, Xingfeng organization: Jinan University – sequence: 8 givenname: Jigang surname: Wang fullname: Wang, Jigang email: jgwang@icmm.ac.cn organization: China Academy of Chinese Medical Sciences – sequence: 9 givenname: Ke orcidid: 0000-0001-9016-812X surname: Ding fullname: Ding, Ke email: dingke@jnu.edu.cn organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 10 givenname: Wencai orcidid: 0000-0002-2810-1001 surname: Ye fullname: Ye, Wencai email: chywc@aliyun.com organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China – sequence: 11 givenname: Zhengqiu orcidid: 0000-0002-0433-2147 surname: Li fullname: Li, Zhengqiu email: pharmlzq@jnu.edu.cn organization: International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of China |
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| Title | 2H‑Azirine-Based Reagents for Chemoselective Bioconjugation at Carboxyl Residues Inside Live Cells |
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