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Published on: August 19, 2012
Photochemical generation of C4'-oxidized abasic site containing oligodeoxynucleotide and its efficient amine
Mariko Aso1, Kazuteru Usui, Mitsuhiro Fukuda
1Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan 812-8582. aso@phar.kyushu-u.ac.jp
Abstract:
[Structure: see text] We synthesized oligodeoxynucleotide (ODN, 3), which contains 4'-o-nitrobenzyloxythymidine (4) as a caged precursor of C4'-oxidized abasic site (1). 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 the duplex.
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