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• W2026942018 endingPage "6480" @default.
• W2026942018 startingPage "6480" @default.
• W2026942018 abstract "NiII-flavonolate complexes [NiIILR(fla)] (LRH: 2-{[bis(pyridin-2-ylmethyl)amino]methyl}-p/m-R-benzoic acid, R: p-OMe (1), p-Me (2), m-Br (4) and m-NO2 (5), fla: flavonolate) were synthesized and characterized with relevance to structural and functional models for the ES (enzyme–substrate) adduct of the NiII-containing quercetin 2,3-dioxygenase (2,3-QD). Their structures, spectroscopic features, redox properties and the reactivity toward molecular oxygen have been investigated. The complexes show a similar distorted octahedral structure and higher enzyme-type dioxygenation reactivity than other reported metal-flavonolate complexes in the oxidative O-heterocyclic ring-opening of the bound substrate flavonolate at lower temperature owing to the introduced carboxylate group in the supporting model ligands. The reaction rate shows first-order dependence on both of the complex and O2 and the second-order rate constant k fits a Hammett linear free energy relationship (ρ = −0.71) for the substituent group in the supporting model ligand LR. The complexes exhibit substituent group dependent structures, properties and reactivity and there are some relationship among them, which could be ascribed to the electronic nature of the substituent group via the benzoate, NiII ion and O(4)C(27)–C(21)C(22) “electron conduit”. In a word, the stronger electron donating group could induce a smaller torsion angle, larger λmax and lower redox potential of the bound flavonolate, making a higher reactivity finally. This study is the first example of a series of structural and functional ES models of the NiII-containing 2,3-QD, providing important insights into the structure–property–reactivity relationship, the electronic substituent effects and carboxylate effects on the enzymatic reactivity and the catalytic role of the NiII-containing 2,3-QD." @default.
• W2026942018 created "2016-06-24" @default.
• W2026942018 creator A5025095617 @default.
• W2026942018 creator A5043379662 @default.
• W2026942018 creator A5086837371 @default.
• W2026942018 date "2014-01-01" @default.
• W2026942018 modified "2023-10-16" @default.
• W2026942018 title "A series of NiII-flavonolate complexes as structural and functional ES (enzyme-substrate) models of the NiII-containing quercetin 2,3-dioxygenase" @default.
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• W2026942018 doi "https://doi.org/10.1039/c3dt53349b" @default.
• W2026942018 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24622725" @default.
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