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^oxoT) 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.