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Open AccessCommunication

8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON L2S 3A1, Canada
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Author to whom correspondence should be addressed.
Academic Editor: Stefano D’Errico
Molbank 2020, 2020(1), M1119; https://doi.org/10.3390/M1119 (registering DOI)
Received: 18 February 2020 / Revised: 27 February 2020 / Accepted: 28 February 2020 / Published: 6 March 2020
(This article belongs to the Special Issue Molecules from Side Reactions)
3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2′-deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2′-deoxyguanosine and C8:5′-O-cyclo-2′-deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis. View Full-Text
Keywords: 8-Fluoro-2′-deoxyguanosine; 19F NMR spectroscopy; fluorination; solid phase synthesis; phosphoramidite 8-Fluoro-2′-deoxyguanosine; 19F NMR spectroscopy; fluorination; solid phase synthesis; phosphoramidite
MDPI and ACS Style

Solodinin, A.; Helmkay, J.; Ollivier, S.; Yan, H. 8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity. Molbank 2020, 2020, M1119.

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