Fluorinated 7-deazapurine 2'-deoxyribonucleosides: modification at the nucleobase and the sugar moiety
Frank Seela1, Kuiying Xu, Padmaja Chittepu
1Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Münster, Germany. frank.seela@cemi-osnabruck.de
Nucleosides, Nucleotides & Nucleic Acids
|December 11, 2007
Abstract:
7-Deaza-7-fluoro-purine 2'-deoxynucleosides as well as 2'-deoxy-2'-fluoroarabinofuranosyl nucleosides 1-8 were synthesized. The fluorine atom was introduced on the base level with Selectfluor. Nucleobase-anion glycosylation was then employed to form the nucleosides. Properties of the fluorine compounds were studied in solution and in solid state. Compound 4a was incorporated into oligonucleotides where the stabilizing effect was observed.
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