Preparation of Peptide Selenoesters from Their Corresponding Acyl Hydrazides†
Yunxue Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorJiazhi Liu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorQingqing Zhou
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorJie Zhao
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Ping Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]Search for more papers by this authorYunxue Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorJiazhi Liu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorQingqing Zhou
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorJie Zhao
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Ping Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]Search for more papers by this author†Dedicated to the Special Issue of Xplorer Prize in 2020.
Main observation and conclusion
Selenoesters are useful substitutes for traditional thioesters in protein ligation chemistry due to their high reactivity in the trans-thio/selenoesterification reaction. However, existing synthetic routes to access peptide selenoester require a selenoesterification reaction between a selenide and a protected peptide with a free carboxylate at the C-terminus. Herein, we introduce an efficient method to convert peptide acyl hydrazide, a convenient thioester surrogate, into the desired selenoester for peptide ligation. Our methodology can be applied to fully de-protected peptides with various C-terminal amino acid residues in high yield without racemization. We believe that this method provides a useful alternative to access peptide C-terminal selenoesters for protein ligation.
Supporting Information
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Appendix S1: Supporting Information |
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