A nonafluoro nucleoside as a sensitive 19f NMR probe of nucleic acid conformation.
A nucleoside carrying a perfluorinated tert-butyl group ( 4) was prepared by a Sonogashira coupling of 5-iodo-2'-deoxyuridine with 4,4,4-trifluoro-3,3-bis(trifluoromethyl)-1-butyne in nearly quantitative yield and subsequently incorporated into DNA oligomers. Thermal denaturation studies showed that 4 had a negligible effect on duplex stability when compared to thymidine. Transition from single strand to duplex was monitored by (19)F NMR spectroscopy at micromolar concentrations of oligomers, demonstrating the sensitivity of 4 as an NMR reporter nucleoside.
Department of Chemistry, University of Washington, Seattle, Washington 98195, USA.
Nivrutti B
NB
Barhate
Rekha N
RN
Barhate
Pavol
P
Cekan
Gary
G
Drobny
Snorri Th
ST
Sigurdsson
D017611:Fluorine Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D012680:Sensitivity and Specificity; D044366:Transition Temperature
D017611:Fluorine Compounds; D009705:Nucleosides