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Nucleic Acids Symposium Series 2006 50(1):169-170; doi:10.1093/nass/nrl084
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© 2006 Oxford University Press

Photochemical generation of C4'-oxidized abasic site containing oligonucleotide and its amine modification reaction

Kazuteru Usui1, Mariko Aso1, Yukiko Toguchi1, Yoshie Kakihara2, Tsuyoshi Goromaru2 and Hiroshi Suemune1

1 Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan, 2 Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama 729-0292, Japan

We studied photochemical generation of oligodeoxynucleotide (ODN) containing C4'-oxidized abasic site (1) from its caged precursor 3. Photoirradiation of 3 at 365 nm followed by amine treatment under neutral conditions afforded the lactam (2) efficiently. Duplexed ODN 3 was converted to 1 faster and more efficiently than single stranded 3, whereas amine treatment of 1 formed from single stranded 3 resulted in slightly faster lactam formation than with duplex.


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