Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion.

Eriko Tomi, Mariko Aso, Satoshi Inoue, Yukiko Toguchi, Kazuteru Usui, Mai Hamdy Azam, Akiko Jinnouchi, Hiroshi Suemune

Research output: Contribution to journalMeeting 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.

Original languageEnglish
Pages (from-to)185-186
Number of pages2
JournalNucleic acids symposium series (2004)
Issue number53
Publication statusPublished - 2009

All Science Journal Classification (ASJC) codes

  • Medicine(all)


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