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Bioinspired Trispyrazolylborato Nickel(II) Flavonolate Complexes and Their Reactivity Toward Dioxygen
Author(s) -
Hoof Santina,
Limberg Christian
Publication year - 2019
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201800457
Subject(s) - chemistry , reactivity (psychology) , nickel , benzoic acid , dioxygenase , stereochemistry , active site , salicylic acid , enzyme , medicinal chemistry , organic chemistry , biochemistry , medicine , alternative medicine , pathology
Aiming at structural and functional mimics of the active site of the Ni II containing quercetin‐2,4‐dioxygenase Ni II flavonolate complexes Tp*Ni X [Tp* = hydrotris(3,5‐dimethyl)pyrazolylborate, X = 3‐hydroxy flavonolate (Fla), 3‐hydroxy thioflavonolate (SFla), 3‐hydroxy selenoflavonolate (SeFla)] were synthesized and characterized by spectroscopic methods and X‐ray crystallography. The complex Tp*NiFla reacts with O 2 via dioxygenation of bound flavonolate to benzoic acid and salicylic acid as one should expect for a functional model of the enzyme. Modification of the carbonyl function of the flavonolate to the corresponding C=S and C=Se compounds retained dioxygenase like reactivity, but did not lead to an increase of reaction rate as had been anticipated due to a weaker interaction of S/Se with the central nickel atom.