Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification

Mariko Aso, Kazuteru Usui, Mitsuhiro Fukuda, Yoshie Kakihara, Tsuyoshi Goromaru, Hiroshi Suemune

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

We synthesized oligodeoxynucleotide (ODN, 3), which contains 4′-o-nitrobenzyloxythymidine (4) as a caged precursor of C4′-oxidized abasic site (1). Photoirradiation of 3 at 365 nm followed by amine treatment under neutral conditions afforded the lactam (2) efficiently. Duplexed ODN 3 was converted to 1 faster and more efficiently than single stranded 3, whereas amine treatment of 1 formed from single stranded 3 resulted in slightly faster lactam formation than with the duplex.

Original languageEnglish
Pages (from-to)3183-3186
Number of pages4
JournalOrganic Letters
Volume8
Issue number15
DOIs
Publication statusPublished - Jul 20 2006

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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