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

20 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

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Lactams
Oligodeoxyribonucleotides
Amines
amines
4'-o-nitrobenzyloxythymidine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification. / Aso, Mariko; Usui, Kazuteru; Fukuda, Mitsuhiro; Kakihara, Yoshie; Goromaru, Tsuyoshi; Suemune, Hiroshi.

In: Organic Letters, Vol. 8, No. 15, 20.07.2006, p. 3183-3186.

Research output: Contribution to journalArticle

Aso, Mariko ; Usui, Kazuteru ; Fukuda, Mitsuhiro ; Kakihara, Yoshie ; Goromaru, Tsuyoshi ; Suemune, Hiroshi. / Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification. In: Organic Letters. 2006 ; Vol. 8, No. 15. pp. 3183-3186.
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