Related Experiment Video
Updated: Aug 12, 2025

Visualizing Lignification Dynamics in Plants with Click Chemistry: Dual Labeling is BLISS!
Published on: January 26, 2018
Direct ring-strain loading for visible-light accelerated bioorthogonal ligation via
Jingshuo Gao1, Qin Xiong1, Xueting Wu1
1Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, 610064, Chengdu, China.
Abstract:
Ultra-fast and selective covalent-bond forming reactions with spatiotemporal controllability are foundational for developing a bioorthogonal approach with high manipulability. However, it is challenging to exploit a reporter functional group to achieve these requirements simultaneously. Here, 11H-Dibenzo[c,f][1,2]diazepine and a set of heterocyclic analogues are investigated for both their photo-switching natures and their ability to serve as dipolarophiles in photo-click reactions with diarylsydnone. Sulfur-containing dibenzothiadiazepine (DBTD) is discovered to be an excellent chemical reporter in cycloaddition with visible-light excitation for in-situ ring-strain loading via its (Z) → (E) photo-isomerization. The bioorthogonal utility of the DBTD tag in spatiotemporally controlled ligation for protein modifications on live cells is also demonstrated.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

