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Comparison of Nonheme Manganese- and Iron-Containing Flavone Synthase Mimics

Lakk-Bogáth, Dóra; Pantalon Juraj, Natalija; Meena, Bashdar I.; Perić, Berislav; Kirin, Srećko I.; Kaizer, József (2021) Comparison of Nonheme Manganese- and Iron-Containing Flavone Synthase Mimics. Molecules, 26 (11). ISSN 1420-3049

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Heme and nonheme-type flavone synthase enzymes, FS I and FS II are responsible for the synthesis of flavones, which play an important role in various biological processes, and have a wide range of biomedicinal properties including antitumor, antimalarial, and antioxidant activities. To get more insight into the mechanism of this curious enzyme reaction, nonheme structural and functional models were carried out by the use of mononuclear iron, [FeII(CDA-BPA*)]2+ (6) [CDABPA = N, N, N’, N’-tetrakis-(2-pyridylmethyl)- cyclohexanediamine], [FeII(CDA-BQA*)]2+ (5) [CDABQA = N, N, N’, N’-tetrakis-(2-quinolilmethyl)- cyclohexanediamine], [FeII(Bn-TPEN)(CH3CN)]2+ (3) [Bn-TPEN = N-benzyl-N, N’, N’-tris(2- pyridylmethyl)-1, 2-diaminoethane], [FeIV(O)(Bn- TPEN)]2+ (9), and manganese, [MnII(N4Py*)(CH3CN)]2+ (2) [N4Py* = N, N-bis(2-pyridylmethyl)-1, 2-di(2-pyridyl) ethylamine)], [MnII(Bn-TPEN)(CH3CN)]2+ (4) complexes as catalysts, where the possible reactive intermediates, high-valent FeIV(O) and MnIV(O) are known and well characterised. The results of the catalytic and stoichiometric reactions showed that the ligand framework and the nature of the metal cofactor significantly influenced the reactivity of the catalyst and its intermediate. Comparing the reactions of [FeIV(O)(Bn-TPEN)]2+ (9) and [MnIV(O)(Bn- TPEN)]2+ (10) towards flavanone under the same conditions, a 3.5-fold difference in reaction rate was observed in favor of iron, and this value is three orders of magnitude higher than was observed for the previously published [FeIV(O)(N2Py2Q*)]2+ [N, N-bis(2-quinolylmethyl)-1, 2-di(2- pyridyl)ethylamine] species.

Item Type: Article
Uncontrolled Keywords: flavone synthase ; iron(IV)-oxo ; manganese(IV)-oxo ; oxidation ; kinetic studies
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Materials Chemistry
Project titleProject leaderProject codeProject type
Minimalni umjetni enzimi: Proširenje primjene posredne indukcije na nove supstrate i nove asimetrične reakcijeKirin, SrećkoIP-2014-09-1461HRZZ
Inovativna rješenja u katalitičkim proizvodnim procesima za potrebe farmaceutske industrijeKirin, SrećkoKK.
Depositing User: Natalija Pantalon Juraj
Date Deposited: 05 Jul 2021 13:29
DOI: 10.3390/molecules26113220

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