Author: Eyer, Luděk ; Růžek, Daniel ; de Clercq, Erik ; Vičar, Tomáš ; Hubálek, Zdeněk ; Raudenská, Matina ; Huvarová, Ivana ; Štefánik, Michal ; Rudolf, Ivo ; Straková, Petra ; Seley-Radtke, Katherine ; Svoboda, Pavel ; Haviernik, Jan ; Balvan, Jan

Emerging flaviviruses are causative agents of severe and life-threatening diseases, against which no approved therapies are available. Among the nucleoside analogues, which represent a promising group of potentially therapeutic compounds, fluorine-substituted nucleosides are characterized by unique structural and functional properties.

01 Aug 2020·Bioorganic & Medicinal ChemistryQ3 · MEDICINE

4′-C-Aminomethyl-2′-deoxy-2′-fluoroarabinonucleoside increases the nuclease resistance of DNA without inhibiting the ability of a DNA/RNA duplex to activate RNase H

Q3 · MEDICINE

Article

Author: Kajino, Ryohei ; Ueno, Yoshihito ; Tsuchihira, Tatsuya ; Maeda, Yusuke

An antisense oligonucleotide is expected as an innovative drug for cancer and hereditary diseases. In this paper, we designed and synthesized DNAs containing a novel nucleoside analog, 1-(4-C-aminomethyl-2-deoxy-2-fluoro-β-d-arabinofuranosyl)thymine, and evaluated their properties. It was revealed that the analog slightly decreases the thermal stability of the DNA/RNA duplex but significantly increases the stability of DNA in a buffer containing bovine serum. Furthermore, it turned out that the DNA/RNA duplex containing the analog is a good substrate for Escherichia coli RNase H. Thus, DNAs containing the nucleoside analog would be good candidates for the development of therapeutic antisense oligonucleotides.

16 Feb 2018·The Journal of Organic ChemistryQ2 · CHEMISTRY

C2′-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level

Q2 · CHEMISTRY

Article

Author: Chattopadhyaya, Jyoti ; Denhez, Clément ; Vianelli Prado, Marcos Joel ; Clivio, Pascale ; Plashkevych, Oleksandr ; Moriou, Céline ; Guillaume, Dominique ; Da Silva, Adilson D.

Fluorine configuration at C2' of the bis(2'-fluorothymidine) dinucleotide is demonstrated to drive intramolecular base stacking. 2'-β F-Configuration drastically reduces stacking compared to the 2'-α series. Hence, base stacking emerges as being tunable by the C2'-F stereoconfiguration through dramatic puckering variations scrutinized by NMR and natural bond orbital analysis. Accordingly, 2'-β F-isomer photoreactivity is significantly reduced compared to that of the 2'-α F-isomer.

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