Activation of fe(Iii)*Bleomycin by 10-hydroperoxy-8,12-octadecadienoic acid

Anand Natrajani, Sidney M. Hecht, Gijs A. Van Der Marel, Jacques H. Van Boom

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Treatment of 10-hydroperoxy-8,12 octadecadienoic acid with Fe(III)-bleomycin (BLM) resulted in reduction of the hydroperoxide to afford 10-oxo-8-decenoic acid, which must form by homolytic scission of the peroxide O-O bond. Although this reaction afforded a reactive species that could demethylate A.N-dimethylaniline and convert styrene to styrene oxide and phenylacetaldehyde, the extent of conversion was much less than that obtained following activation of Fe(III)-BLM with hydrogen peroxide. Further, unlike the activated species formed by admixture of Fe(III)-BLM + H2O2 or ethyl hydroperoxide, the activated Fe-BLM formed via the agency of 10-hydroperoxy-8,12-octadecadienoic acid would not mediate the destruction of the self-complementary oligonucleotide 5’-d(CGCT3A3GCG), nor would it support naphthalene hydroxylation. These results suggest that the activated Fe-BLM formed from Fe(III)-BLM + H2O2 may differ from the species generated when Fe(III)-BLM reacts with alkyl peroxides that undergo homolytic O-O bond scission.

Original languageEnglish (US)
Pages (from-to)4532-4538
Number of pages7
JournalJournal of the American Chemical Society
Volume112
Issue number11
DOIs
StatePublished - Jan 1 1990
Externally publishedYes

ASJC Scopus subject areas

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

Fingerprint

Dive into the research topics of 'Activation of fe(Iii)*Bleomycin by 10-hydroperoxy-8,12-octadecadienoic acid'. Together they form a unique fingerprint.

Cite this