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Updated: Dec 13, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Enzyme- or light-triggered cyclopropenes for bioorthogonal ligation
Ting Jiang1, Scott T Laughlin2
1Department of Chemistry, Stony Brook University, Stony Brook, NY, United States.
Bioorthogonal reactions enable biological investigation. This review covers classic and new methods, highlighting light- or enzyme-activated "turn-on" cyclopropenes for in vitro and in vivo studies.
Area of Science:
- Chemical Biology
- Organic Chemistry
- Biotechnology
Background:
- Bioorthogonal reactions are crucial for studying biological systems.
- Classic methods include Staudinger-Bertozzi ligation and SPAAC.
- Recent advancements focus on "turn-on" reactions activated by external stimuli.
Purpose of the Study:
- To review established and emerging bioorthogonal reactions.
- To discuss the advantages and disadvantages of light- or enzyme-activated reactions.
- To introduce novel "turn-on" cyclopropenes for bioorthogonal chemistry.
Main Methods:
- Review of literature on bioorthogonal reactions.
- Discussion of "turn-on" reaction mechanisms (light, enzyme).
- Synthesis and in vitro/in vivo evaluation of caged cyclopropenes.
Main Results:
- Overview of Staudinger-Bertozzi ligation, SPAAC, 1,3-dipolar cycloaddition, and tetrazine-alkene ligation.
- Analysis of "turn-on" bioorthogonal reaction capabilities and limitations.
- Demonstration of modular "turn-on" cyclopropene design and reactivity.
Conclusions:
- "Turn-on" bioorthogonal reactions offer enhanced control and specificity.
- Light- and enzyme-activated cyclopropenes represent a promising new class of reagents.
- Developed cyclopropenes show potential for versatile in vitro and in vivo applications.
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