Fluorinated 7-deazapurine 2'-deoxyribonucleosides: modification at the nucleobase and the sugar moiety.
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.
Seela
Frank
F
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Münster, Germany. frank.seela@cemi-osnabruck.de
Xu
Kuiying
K
Chittepu
Padmaja
P
Ming
Xin
X
D002241:Carbohydrates / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D013816:Thermodynamics; D044366:Transition Temperature
C512929:7-deazapurine; D002241:Carbohydrates; D003853:Deoxyribonucleosides; D017611:Fluorine Compounds; D011687:Purines