2-Oxoalkyl caged oligonucleotides: one-electron reductive activation into emergence of ordinary hybridization property by hypoxic X-irradiation.
Ionizing radiation triggers the activation of caged oligodeoxynucleotides (ODNs) with a 2-oxoalkyl leaving group to give the corresponding normal uncaged strands. We designed and synthesized ODNs caged by a 2-oxopropyl group at a given thymine N(3) position (d(oxo)T) to evaluate their one-electron reduction characteristics. Upon hypoxic X-radiolysis in aqueous solution, the caged ODNs released the 2-oxopropyl group to produce the corresponding uncaged ODNs. Digestion by a restriction enzyme Swa I revealed that caged ODN pre-irradiated in hypoxia could form an ordinary duplex with its complementary strand.
Tanabe
Kazuhito
K
Department of Energy and Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University, Katsura campus, Kyoto, 615-8510, Japan. tanabeka@scl.kyoto-u.ac.jp
Kanezaki
Hiroshi
H
Ishii
Hirotake
H
Nishimoto
Sei-Ichi
S
D000693:Anaerobiosis; D004583:Electrons; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D010084:Oxidation-Reduction; D014965:X-Rays
D009838:Oligodeoxyribonucleotides