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

被引:41
作者
Matuz, Andrea [1 ]
Giorgi, Michel
Speier, Gabor [1 ]
Kaizer, Jozsef [1 ]
机构
[1] Univ Pannonia, Dept Chem, H-8201 Veszprem, Hungary
关键词
Flavonol dioxygenase; Synthetic model; Dioxygenation; Kinetics and mechanism; Transition metals; ACIREDUCTONE DIOXYGENASE; CRYSTAL-STRUCTURE; OXALATE OXIDASE; FLAVONOL 2,4-DIOXYGENASE; METAL-COMPLEXES; SUPEROXIDE; REACTIVITY; COORDINATION; OXYGENATION; MECHANISM;
D O I
10.1016/j.poly.2013.07.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of divalent transition metal (Mn, Fe, Co, Ni, and Cu) flavonolate (Fla) complexes M-II(Fla)(L-1), and M-II(Fla)(L-2)X (X = Cl or ClO4) with the ligands N-propanoate-N,N-bis(2-pyridylmethyl)amine (L-1 = HPBMPA) and N-methylpropanoate-N,N-bis(2-pyridylmethyl)amine (L-2 = 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 (pi-pi*) of the coordinated flavonolate is influenced by the metals, and a linear correlation was observed between the logarithm of the reaction rate constant with O-2 and the degree of the bathochromic shift (Delta lambda), providing a mechanistic insight into the stoichiometric dioxygenation reactions. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:41 / 49
页数:9
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