A Nonafluoro Nucleoside as a Sensitive 19F NMR Probe of Nucleic Acid Conformation
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- 作者：Nivrutti B. Barhate ; Rekha N. Barhate ; Pavol Cekan ; Gary Drobny ; Snorri Th. Sigurdsson
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：July 3, 2008
- 年：2008
- 卷：10
- 期：13
- 页码：2745 - 2747
- 全文大小：199K
- 年卷期：v.10,no.13(July 3, 2008)
- ISSN：1523-7052
文摘
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 stabilty when compared to thymidine. Transition from single strand to duplex was monitored by 19F NMR spectroscopy at micromolar concentrations of oligomers, demonstrating the sensitivity of 4 as an NMR reporter nucleoside.