title: 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.
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.
authors.affiliation: Department of Chemistry, University of Pannonia, Veszprém, Hungary.
authors.forename: József S
authors.initials: JS
authors.lastname: Pap
authors.forename: Andrea
authors.initials: A
authors.lastname: Matuz
authors.forename: Gábor
authors.initials: G
authors.lastname: Baráth
authors.forename: Balázs
authors.initials: B
authors.lastname: Kripli
authors.forename: Michel
authors.initials: M
authors.lastname: Giorgi
authors.forename: Gábor
authors.initials: G
authors.lastname: Speier
authors.forename: József
authors.initials: J
authors.lastname: Kaizer
mesh_terms: D002384:Catalysis; D049308:Dioxygenases / Q000378:metabolism*; D044948:Flavonols / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry*
chemical_list: D044948:Flavonols; D015363:Quinolones; D007501:Iron; D049308:Dioxygenases