Aerobic Baeyer–Villiger Oxidation Catalyzed by a Flavin‐Containing Enzyme Mimic in Water

Direct incorporation of molecular oxygen into small organic molecules has attracted much attention for the development of new environmentally friendly oxidation processes. In line with this approach, bioinspired systems mimicking enzyme activities are of particular interest since they may perform ca...

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Veröffentlicht in:Angewandte Chemie 2018-12, Vol.130 (50), p.16650-16653
Hauptverfasser: Chevalier, Yoan, Lock Toy Ki, Yvette, le Nouen, Didier, Mahy, Jean‐Pierre, Goddard, Jean‐Philippe, Avenier, Frédéric
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Sprache:eng
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Zusammenfassung:Direct incorporation of molecular oxygen into small organic molecules has attracted much attention for the development of new environmentally friendly oxidation processes. In line with this approach, bioinspired systems mimicking enzyme activities are of particular interest since they may perform catalysis in aqueous media. Demonstrated herein is the incorporation of a natural flavin cofactor (FMN) into the specific microenvironment of a water‐soluble polymer which allows the efficient reduction of the FMN by NADH in aqueous solution. Once reduced, this artificial flavoenzyme can then activate molecular dioxygen under aerobic conditions and result in the Baeyer–Villiger reaction at room temperature in water. Sauerstoffaktivierung: Die Einführung von Flavin‐Cofaktoren (FMN) in die lokale hydrophobe Mikroumgebung eines modifizierten Polyethylenimins ermöglicht die Aktivierung von Disauerstoff in Gegenwart von NADH. Diese Aktivierung führt zu einer erfolgreichen Baeyer‐Villiger‐Reaktion bei Raumtemperatur in Wasser.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201810124