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Baeyer-Villiger monooxygenases (BVMOs) as entry to lactones and their polyesters

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Abstract

Baeyer-Villiger monooxygenases (BVMOs) offer an attractive alternative for the synthesis of lactones, which can be used for the preparation of polyesters by ring opening polymerization. While chemical oxidation usually requires the use of toxic oxidative reagents, enzymatic oxidation is performed using molecular oxygen under mild conditions. Moreover, the main advantage of biocatalyzed Bayer-Villiger oxidations over chemical alternatives is their regio-selectivity. Indeed, the structure of the monomer that is polymerized can greatly influence the polyester’s properties and therefore its application (solubility, thermal properties).
The activity of a spectrum of BVMOs on various cyclic ketones was screened in order to broaden the range of lactones as precursors for polyesters that can be synthesized by biocatalysis. Activity of the biocatalysts was measured using a spectrophotometric screening method based on nicotinamide co-factor consumption during the oxidation reaction. Combinations of ketones and BVMOs displaying activity were further investigated to analyze the structure of the oxidation products. Finally, some ketones were selected for upscaling of the biocatalyzed production of lactones at the gram scale using BVMOs.
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Original languageEnglish
Publication statusPublished - 9 Jul 2017