Related Experiment Video
Updated: Aug 11, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
The thiol-sulfoxonium ylide photo-click reaction for bioconjugation
Chuan Wan1, Zhanfeng Hou1, Dongyan Yang2
1State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen 518055 P. R. China lizg.sz@pku.edu.cn lizg@szbl.ac.cn.
Abstract:
Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current methods suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report a transition metal-free thiol-sulfoxonium ylide photo-click reaction that enables bioconjugation under bio-compatible conditions. The reaction is highly cysteine-selective and generally finished within minutes with naturally occurring riboflavin derivatives as organic photocatalysts. The catalysts and substrates are readily accessible and bench stable and have satisfactory water solubility. As a proof-of-concept study, the reaction was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore the druggable content of the human proteome.
Related Concept Videos
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Phase II Reactions: Glutathione Conjugation and Mercapturic Acid Formation
Several distinctive characteristics distinguish glutathione conjugation from other phase II...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Phase II Conjugation Reactions: Overview
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

