Cerium(IV)-mediated oxidation of flavonol with relevance to flavonol 2,4-dioxygenase. Direct evidence for spin delocalization in the flavonoxy radical

József Kaizer, Ildikó Ganszky, Gábor Speier, Antal Rockenbauer, László Korecz, Michel Giorgi, Marius Réglier, Serge Antonczak

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Abstract

The cerium(IV)-mediated oxidation of 3-hydroxy-4′-methylflavone (1) proceeds by H-atom abstraction forming the flavonoxy radical (7), and the subsequent combination of its resonance forms leads to the 3-hydroxy-4′-methylflavone dehydro dimer (9). The above system serves as direct evidence for the intermediacy of the flavonoxy radical, its spin delocalization, and also indirect evidence for valence tautomerism as a key step on the substrate activation both in the quercetinase and its biomimic model system.

Original languageEnglish
Pages (from-to)893-899
Number of pages7
JournalJournal of Inorganic Biochemistry
Volume101
Issue number6
DOIs
Publication statusPublished - Jun 1 2007

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Keywords

  • CAN
  • Flavonol 2,4-dioxygenase
  • Flavonoxy radical
  • Valence tautomerism

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

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