title: Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion.
abstract: The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions induced by antitumor bleomycins. The reactivity of 1 with amine under neutral conditions giving lactam 2 and its structural similarity to unmodified DNA suggested the possibility that ODN containing 1 could react with proteins which interact with DNA at lysine residue. In order to provide nucleic acid analogues with useful lysine modifying reactivity, we planned to study reaction of 2'-substituted analogues of 1, such as 3-5, with amine and their corresponding caged precursors 6-8 were synthesized. Uncaging reaction of 16 containing 6 proceeded efficiently. The reaction of obtained 17 containing 3 with Z-Lys-OH did not afford products corresponding to lactam. However, HPLC analysis of the reaction mixture suggested interaction of 3 with Z-Lys-OH.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
authors.forename: Eriko
authors.initials: E
authors.lastname: Tomi
authors.forename: Mariko
authors.initials: M
authors.lastname: Aso
authors.forename: Satoshi
authors.initials: S
authors.lastname: Inoue
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Toguchi
authors.forename: Kazuteru
authors.initials: K
authors.lastname: Usui
authors.forename: Mai Hamdy
authors.initials: MH
authors.lastname: Azam
authors.forename: Akiko
authors.initials: A
authors.lastname: Jinnouchi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Suemune
mesh_terms: D004249:DNA Damage; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D009838:Oligodeoxyribonucleotides