ArticleThe Journal of organic chemistry2015
Synthesis and properties of 2'-deoxy-2',4'-difluoroarabinose-modified nucleic acids.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Exploration of 4'-fluoro fleximer nucleoside analogues as potential broad-spectrum antiviral agents.Bioorganic & medicinal chemistry · 2025Article
- Fluorinated carbohydrates forChemical Society reviews · 2023Review
- Tellurium-Modified Nucleosides, Nucleotides, and Nucleic Acids with Potential Applications.Molecules (Basel, Switzerland) · 2022Review
- 4'-SCFAngewandte Chemie (International ed. in English) · 2022Article
- siRNAs containing 2'-fluorinated Northern-methanocarbacyclic (2'-F-NMC) nucleotides: in vitro and in vivo RNAi activity and inability of mitochondrial polymerases to incorporate 2'-F-NMC NTPs.Nucleic acids research · 2021Article
- Influence of 4'-Substitution on the Activity of Gemcitabine and Its ProTide Against VZV and SARS-CoV-2.ACS medicinal chemistry letters · 2021Article
- Beyond ribose and phosphate: Selected nucleic acid modifications for structure-function investigations and therapeutic applications.Beilstein journal of organic chemistry · 2021Review
- Synthesis and Conformational Analysis of Fluorinated Uridine Analogues Provide Insight into a Neighbouring-Group Participation Mechanism.Molecules (Basel, Switzerland) · 2020Article
- Synthesis, biophysical properties, and RNase H activity of 6'-difluoro[4.3.0]bicyclo-DNA.Beilstein journal of organic chemistry · 2019Article
- Structural basis for the synergy of 4'- and 2'-modifications on siRNA nuclease resistance, thermal stability and RNAi activity.Nucleic acids research · 2018Article
- Synthesis and Antisense Properties of 2'β-F-Arabinouridine Modified Oligonucleotides with 4'-Molecules (Basel, Switzerland) · 2018Article
- 6'-Fluoro[4.3.0]bicyclo nucleic acid: synthesis, biophysical properties and molecular dynamics simulations.Beilstein journal of organic chemistry · 2018Article
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Authors and funding
10 authors.
Funding
Abstract
We report the synthesis, thermal stability, and RNase H substrate activity of 2'-deoxy-2',4'-difluoroarabino-modified nucleic acids. 2'-Deoxy-2',4'-difluoroarabinouridine (2,'4'-diF-araU) was prepared in a stereoselective way in six steps from 2'-deoxy-2'-fluoroarabinouridine (2'-F-araU). NMR analysis and quantum mechanical calculations at the nucleoside level reveal that introduction of 4'-fluorine introduces a strong bias toward the North conformation, despite the presence of the 2'-βF, which generally steers the sugar pucker toward the South/East conformation. Incorporation of the novel monomer into DNA results on a neutral to slightly stabilizing thermal effect on DNA-RNA hybrids. Insertion of 2',4'-diF-araU nucleotides in the DNA strand of a DNA-RNA hybrid decreases the rate of both human and HIV reverse transcriptase-associated RNase H-mediated cleavage of the complement RNA strand compared to that for an all-DNA strand or a DNA strand containing the corresponding 2'-F-araU nucleotide units, consistent with the notion that a 4'-fluorine in 2'-F-araU switches the preferred sugar conformation from DNA-like (South/East) to RNA-like (North).
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