Site-Selective Itaconation of Complex Peptides by Photoredox Catalysis
Dr. Siyao 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorDr. QingQing 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorDr. Xiaheng Zhang
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 China
Search for more papers by this authorCorresponding Author
Prof. 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorDr. Siyao 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorDr. QingQing 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorDr. Xiaheng Zhang
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 China
Search for more papers by this authorCorresponding Author
Prof. 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, No. 800, Dongchuan Rd, Shanghai, 200240 China
Search for more papers by this authorAbstract
Site-selective peptide functionalization provides a straightforward and cost-effective access to diversify peptides for biological studies. Among many existing non-invasive peptide conjugations methodologies, photoredox catalysis has emerged as one of the powerful approaches for site-specific manipulation on native peptides. Herein, we report a highly N-termini-specific method to rapidly access itaconated peptides and their derivatives through a combination of transamination and photoredox conditions. This strategy exploits the facile reactivity of peptidyl-dihydropyridine in the complex peptide settings, complementing existing approaches for bioconjugations with excellent selectivity under mild conditions. Distinct from conventional methods, this method utilizes the highly reactive carbamoyl radical derived from a peptidyl-dihydropyridine. In addition, this itaconated peptide can be further functionalized as a Michael acceptor to access the corresponding peptide-protein conjugate.
Conflict of interest
The authors declare no conflict of interest.
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