Efficient Synthesis of Trifluoromethylated Purine Ribonucleosides and Ribonucleotides.
Mikolaj Chrominski1, Joanna Kowalska2, Jacek Jemielity1
1Centre of New Technologies, University of Warsaw, Warsaw, Poland.
Current Protocols in Nucleic Acid Chemistry
|September 29, 2020
Summary
This study details the synthesis of trifluoromethylated guanosine and adenosine nucleotides and nucleosides. These methods provide access to novel CF3-containing compounds for further research.
Area of Science:
- Organic Chemistry
- Nucleoside Chemistry
- Medicinal Chemistry
Background:
- Trifluoromethylated nucleosides are valuable in medicinal chemistry and molecular biology.
- Existing synthetic routes for trifluoromethylated purines are limited.
Purpose of the Study:
- To present detailed protocols for synthesizing trifluoromethylated guanosine and adenosine derivatives.
- To enable the preparation of trifluoromethylated nucleoside phosphates.
Main Methods:
- Trifluoromethylation of protected nucleosides.
- Deprotection to yield CF3-containing nucleosides.
- Phosphorylation and phosphate elongation.
Main Results:
- Successful synthesis of 8-CF3-guanosine and 8-CF3, 2-CF3, and 2,8-diCF3-adenosine derivatives.
- Preparation of corresponding mono-, di-, and triphosphates.
- Detailed support protocols for handling, purification, and analysis.
Conclusions:
- The described protocols offer robust synthetic access to a range of trifluoromethylated purine nucleosides and nucleotides.
- These compounds can serve as building blocks for novel therapeutics and biochemical tools.
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