Bio-inspired flavonol and quinolone dioxygenation by a non-heme iron catalyst modeling the action of flavonol and 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases

József S. Pap, Andrea Matuz, Gábor Baráth, Balázs Kripli, Michel Giorgi, Gábor Speier, József Kaizer

Research output: Article

17 Citations (Scopus)

Abstract

The mononuclear complex, Fe III(O-bs)(salen) (salenH 2 = 1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene; O-bsH = O-benzoylsalicylic acid) was synthesized as synthetic enzyme-depside complex, and characterized by spectroscopic methods and X-ray crystal analysis. The dioxygenation of flavonol (flaH) and 3-hydroxy-4-quinolone (quinH 2) derivatives in the presence of catalytic amounts of Fe III(O-bs)(salen) results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylic and anthranilic acid derivatives with concomitant release of carbon monoxide. These reactions can be regarded as biomimetic functional models with relevance to the iron-containing flavonol and the cofactor-independent 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases.

Original languageEnglish
Pages (from-to)15-21
Number of pages7
JournalJournal of Inorganic Biochemistry
Volume108
DOIs
Publication statusPublished - márc. 1 2012

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

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