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Nucleic Acids Symposium Series 2001 1(1):115-116; doi:10.1093/nass/1.1.115
© 2001 by Oxford University Press
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Synthesis and properties of a new class of nueleosides with spin source

Mariko Aso, Takeshi Ikeno, Toshiyuki Kaneko, Noboru Koga and Hiroshi Suemune

Graduate School of Pharmaceutical Sciences, Kyushu University, Midashi, Higashiku, Fukuoka 812-8582, Japan

Novel spin-labeled ribonucleosides 1-5 were synthesized to investigate stability and behavior of N-tert-butyl aminoxyl radical on nucleobase. Site selective lithiation of tri-O-protected ribonucleosides followed by the reaction with 2-methyl-2-nitrosopropane (MNP) resulted in introduction of N-tert-butylhydroxylamino group into various positions of purine or pyrimidine nucleus. Oxidation of the obtained hydroxylamines with Ag2O led to formation of 1–5. EPR study showed that the unpaired electron of the aminoxyl radical was delocalized into the nucleobase and hyperfine structures were dependent on the position of the radical.


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