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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.
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.
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