Synthesis and Biophysical Characterization of RNAs Containing 2'-Fluorinated Northern Methanocarbacyclic Nucleotides
| Autor: | Masaaki Akabane-Nakata, Shigeo Matsuda, Martin Egli, Muthiah Manoharan, Namrata D. Erande, Pawan Kumar, Rajat S. Das |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Oligonucleotide Chemistry Stereochemistry Organic Chemistry RNA 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Nucleobase Duplex (building) Lipophilicity Thermal stability Nucleotide Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 21(7) |
| ISSN: | 1523-7052 |
| Popis: | 2'-Fluorinated Northern methanocarbacyclic (2'-F-NMC) nucleosides and phosphoramidites, based on a bicyclo[3.1.0]hexane scaffold bearing all four natural nucleobases (U, C, A, and G), were synthesized to enable exploration of this novel nucleotide modification related to the clinically validated 2'-deoxy-2'-fluororibonucleotides (2'-F-RNA). Biophysical properties of the 2'-F-NMC-containing oligonucleotides were evaluated. A duplex of 2'-F-NMC-modified oligonucleotide with RNA exhibited thermal stability similar to that of the parent RNA duplex, 2'-F-NMC-modified oligonucleotides had higher stability against 5'- and 3'-exonucleolytic degradation than the corresponding oligonucleotides modified with 2'-F-RNA, and 2'-F-NMC-modified oligonucleotides exhibited higher lipophilicity than the corresponding RNA oligonucleotides as well as those modified with 2'-F-RNA. |
| Databáze: | OpenAIRE |
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