A nonafluoro nucleoside as a sensitive 19f NMR probe of nucleic acid conformation |
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Authors: | Barhate Nivrutti B Barhate Rekha N Cekan Pavol Drobny Gary Sigurdsson Snorri Th |
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Affiliation: | Department of Chemistry, University of Washington, Seattle, Washington 98195, USA. |
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Abstract: | 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. |
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