Biocompatible decarboxylative coupling enabled by N-hydroxynaphthalimide esters

Hongze Liao, Zhiyou Su, Jia Zhang, Shuai Liu, Meng-Jun Fan, Shu-Ping Wang, Fan Sun, Weihua Jiao, Lei Li, Hong-Rui Zhu, Yong-Jun Zhou, Zhizhen Zhang and Hou-Wen Lin ()
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Hongze Liao: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Zhiyou Su: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Jia Zhang: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Shuai Liu: Zhejiang University, Ocean College, Zhoushan Campus
Meng-Jun Fan: Shenyang Pharmaceutical University, College of Traditional Chinese Medicine
Shu-Ping Wang: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Fan Sun: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Weihua Jiao: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Lei Li: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Hong-Rui Zhu: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Yong-Jun Zhou: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism
Zhizhen Zhang: Zhejiang University, Ocean College, Zhoushan Campus
Hou-Wen Lin: Shanghai Jiao Tong University School of Medicine, Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract This study develops a catalyst-free, light-induced decarboxylative coupling utilizing N-hydroxynaphthalimide esters (NHNI esters) as multifunctional reagents, acting as photosensitizers, oxidants, and redox-active esters. In cell lysates, this method efficiently enabled Csp3-Csp3 coupling reactions with silyl enol ethers or Michael acceptors. Substrates with donor-acceptor (D-A) frameworks are found to significantly enhance reaction efficiency, with photophysical characterization showing that efficient D-A framework promotes the formation of charge transfer state (CT), thus improving coupling efficiency. The system was further demonstrated in peptide labeling and DNA-encoded library (DEL) technology for the introduction of diverse alkyl groups. Notably, the successful application of this methodology in live cells is confirmed through confocal microscopy and HRMS, providing an efficient tool for chemical modification in biological systems.

Date: 2025
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DOI: 10.1038/s41467-025-65244-7

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