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Biocompatible decarboxylative coupling enabled by N-hydroxynaphthalimide esters.

Hongze Liao1, Zhiyou Su1, Jia Zhang1

  • 1Department of Pharmacy, Ren Ji Hospital, College of Clinical Pharmacy, State Key Laboratory of Microbial Metabolism, Shanghai Jiao Tong University School of Medicine, Shanghai, China.

Nature Communications
|November 24, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a novel catalyst-free, light-induced reaction using N-hydroxynaphthalimide esters for efficient Csp3-Csp3 coupling. This method enables chemical modifications in biological systems, including live cells.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Chemical Biology

Background:

  • Developing efficient and versatile coupling reactions is crucial for organic synthesis and chemical biology.
  • Catalyst-free and light-induced methods offer sustainable and mild alternatives to traditional synthetic approaches.
  • N-hydroxynaphthalimide (NHNI) esters present potential as multifunctional reagents in photochemical transformations.

Purpose of the Study:

  • To develop a catalyst-free, light-induced decarboxylative coupling method using NHNI esters.
  • To explore the scope and efficiency of this method for Csp3-Csp3 bond formation.
  • To demonstrate the utility of this methodology in biological applications, including live-cell modifications.

Main Methods:

  • Utilizing N-hydroxynaphthalimide esters as photosensitizers, oxidants, and redox-active esters in a light-induced decarboxylative coupling.
  • Investigating Csp3-Csp3 coupling reactions with silyl enol ethers and Michael acceptors in cell lysates.
  • Employing photophysical characterization to understand the role of donor-acceptor (D-A) frameworks in enhancing reaction efficiency via charge transfer (CT) states.
  • Applying the developed methodology to peptide labeling and DNA-encoded library (DEL) technology.
  • Validating the application in live cells using confocal microscopy and high-resolution mass spectrometry (HRMS).

Main Results:

  • Achieved efficient catalyst-free, light-induced Csp3-Csp3 coupling reactions.
  • Demonstrated enhanced reaction efficiency with substrates featuring donor-acceptor (D-A) frameworks, attributed to improved charge transfer (CT) state formation.
  • Successfully applied the method for peptide labeling and introducing diverse alkyl groups in DNA-encoded libraries (DEL).
  • Confirmed the successful application of the methodology in live cells, showcasing its potential for biological modifications.

Conclusions:

  • N-hydroxynaphthalimide esters serve as effective multifunctional reagents for catalyst-free, light-induced decarboxylative coupling.
  • The D-A framework significantly enhances coupling efficiency by promoting charge transfer states.
  • This method provides a versatile and efficient tool for chemical modifications in biological systems, including live cells.