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Updated: Apr 21, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Visible-light-driven bioorthogonal photoclick reaction of o-diones with vinyl amides
Xue Yang1, Bolin Xu1, Xiang Wang2
1State Key Laboratory of Analytical Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry, Chemistry and Biomedicine Innovation Center(ChemBIC), ChemBioMed Interdisciplinary Research Center, Nanjing University, Nanjing 210023, China. jinboli@nju.edu.cn.
Abstract:
Photo-initiated bioorthogonal reactions in the visible-light range allow spatiotemporal labeling or regulation in living systems, which however still remain scarce. To bridge this gap, we established a bioorthogonal o-dione and vinyl ether photocycloaddition (DVPC) reaction driven by visible light as the first-generation o-dione based bioorthogonal reaction (DVPC 1.0). Driven by the demand to expand substrate scope to include electron-rich alkenes with better stability, increased reaction rates and longer excitation wavelengths, herein we report the second-generation DVPC (DVPC 2.0) between o-diones and vinyl amides. Electron-withdrawing substitutions on the o-dione substrates in DVPC 2.0 were found to accelerate the reaction in aqueous solution by up to 50-fold. Some of the DVPC 2.0 substrates allowed two-photon excitation, which red-shifted the excitation wavelength to 700-800 nm. A bifunctional bioorthogonal substrate containing both an N-vinyl group and an azide functionality was prepared, which allowed sequential bioorthogonal reactions on proteins with temporal control.
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