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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: August 19, 2012

Self-Immolative Arylcarbonates for Nucleic Acid Templated Reactions.

Kim-Long Diep¹, Elia Janett¹, Katharina M Fromm¹

¹Department of Chemistry, University of Fribourg, Chemin du Musée 9, Fribourg CH-1700, Switzerland.

The Journal of Organic Chemistry

|July 1, 2025

Summary

This study introduces novel self-immolative carbonate oligonucleotides for enhanced nucleic acid templated reactions. These improved diagnostic tools offer tunable reactivity for faster, more sensitive, and selective molecular detection.

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Area of Science:

Chemical Biology
Oligonucleotide Chemistry
Molecular Diagnostics

Background:

Nucleic acid templated reactions are crucial for developing diagnostic tools and molecular libraries.
Existing amine/carbonate oligonucleotide reactions require performance improvements in speed, sensitivity, and selectivity.

Purpose of the Study:

To synthesize novel halogenated arylcarbonates with self-immolative properties for oligonucleotide conjugation.
To develop improved nucleic acid templated reactions with tunable performance characteristics.

Main Methods:

Synthesis of halogenated arylcarbonates.
Conjugation to alkyne-functionalized oligonucleotides via click chemistry.
Templated reactions between carbonate and amine-bearing oligonucleotides.
Kinetic analysis of reaction substrates and parameters.

Main Results:

Successfully synthesized and conjugated self-immolative carbonate oligonucleotides.
Demonstrated tunable reactivity of carbonate oligonucleotides by modifying electronic and steric properties, and pH.
Presented a detailed kinetic analysis of the templated reactions.

Conclusions:

The developed carbonate oligonucleotides offer a versatile platform for enhancing nucleic acid templated reactions.
Tunable reactivity allows optimization for specific diagnostic or molecular generation applications.
This work advances the performance of oligonucleotide-based templated chemical systems.