A nonafluoro nucleoside as a sensitive 19f NMR probe of nucleic acid conformation.

Nivrutti B Barhate, Rekha N Barhate, Pavol Cekan, Gary Drobny, Snorri Th Sigurdsson

Organic letters 2008 Jul 03

filter terms:

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.

Citation

Nivrutti B Barhate, Rekha N Barhate, Pavol Cekan, Gary Drobny, Snorri Th Sigurdsson. A nonafluoro nucleoside as a sensitive 19f NMR probe of nucleic acid conformation. Organic letters. 2008 Jul 03;10(13):2745-7