title: The photoreactivity of the caged precursors of oligonucleotides containing C4'-oxidized abasic site and reaction of the generated lesion.
abstract: The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions by antitumor bleomycins (BLMs) and the acyclic keto aldehyde incorporated in DNA might react with DNA interacting biomolecules. We synthesized oligodeoxynuceotides 3-caged-1 and 3-caged-2 as caged precursors of 3, an ODN containing 1, to study the reactivities of 3 with amine. Irradiation of double stranded 3-caged-1 led to efficient formation of 3 compared to its single stranded form. Similarly, 3-caged-2 and its duplex afforded 3. With 3-caged-2, yields of 3 were lower compared to 3-caged-1. Formation of the duplex slowed decaging rate down but the yield of 3 was higher than that of single stranded 3-cage-2. Reaction of the obtained 3 with amine resulted in the formation of lactam 2b in good yield.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
authors.forename: Kazuteru
authors.initials: K
authors.lastname: Usui
authors.forename: Mariko
authors.initials: M
authors.lastname: Aso
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Fukuda
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Toguchi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Suemune
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry*; D001665:Binding Sites; D004249:DNA Damage; D004268:DNA-Binding Proteins / Q000737:chemistry*; D007700:Kinetics; D007769:Lactams / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D010782:Photolysis
chemical_list: D001426:Bacterial Proteins; D004268:DNA-Binding Proteins; C066312:DnaA protein, Bacteria; D007769:Lactams; D009838:Oligodeoxyribonucleotides