Structural and functional comparison of manganese-, iron-, cobalt-, nickel-, and copper-containing biomimic quercetinase models

Andrea Matuz, Michel Giorgi, Gábor Speier, József Kaizer

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

A series of divalent transition metal (Mn, Fe, Co, Ni, and Cu) flavonolate (Fla) complexes MII(Fla)(L1), and MII(Fla) (L2)X (X=Cl or ClO4) with the ligands N-propanoate-N, N-bis(2-pyridylmethyl)amine (L1 = HPBMPA) and N-methylpropanoate-N, N-bis(2-pyridylmethyl)amine (L2 = MPBMPA) have been prepared and characterized by spectroscopic methods and two cases by X-ray crystal analysis. The coordination sphere of the central ions is distorted octahedral with N 3 or N3O donor sets, which are good structural models for the cupin-type metal-containing flavonol 2,4-dioxygenases (FDO). The dioxygenation of the metal flavonolate complexes results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylate complexes and carbon monoxide as biomimic FDO models. The bathochromic shift of the absorption band I (π-π*) of the coordinated flavonolate is influenced by the metals, and a linear correlation was observed between the logarithm of the reaction rate constant with O2 and the degree of the bathochromic shift (Dk), providing a mechanistic insight into the stoichiometric dioxygenation reactions.

Original languageEnglish
Pages (from-to)41-49
Number of pages9
JournalPolyhedron
Volume63
DOIs
Publication statusPublished - Jan 1 2013

Keywords

  • Dioxygenation
  • Flavonol dioxygenase
  • Kinetics and mechanism
  • Synthetic model
  • Transition metals

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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