Bleomycin-Mediated Degradation of Aristeromycin-Containing DNA. Novel Dehydrogenation Activity of Iron-Bleomycin

Hiroshi Sugiyama, Takashi Sera, Yukihiro Dannoue, Isao Saito, Ryuji Marumoto

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The antitumor antibiotic bleomycin (BLM) induces C-H bond scission at the C4′ of deoxyribose moiety of DNA in the presence of Fe(II) and 02. To investigate the primary oxidation step, 2′-deoxyaristeromycin (Ar) possessing a cyclopentane ring instead of a ribofuranose ring was incorporated into the BLM-cleaving site of synthetic oligonucleotide d(GGArAGG). It was found that an unprecedented dehydrogenation occurs effectively at the C4′ and C6′ positions of the Ar moiety to give 2′-deoxyneplanocin A containing oligonucleotide together with a minor but stereospecific C4′ hydroxylation in the Fe11- BLM-mediated degradation of duplex d(GGArAGG)-d(CCTTCC). An intermediate C4′ carbocation derived from one-electron oxidation of initially formed C4′ radical has been proposed for the dehydrogenation reaction.

Original languageEnglish
Pages (from-to)2290-2295
Number of pages6
JournalJournal of the American Chemical Society
Volume113
Issue number6
DOIs
Publication statusPublished - Jan 1 1991
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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