Baeyer-Villiger monooxygenases resolution

Enantioselective Kinetic Resolution of Racemic 3-Phenylbutan-2-one Using a Baeyer-Villiger Monooxygenase... 

Kirschner, A. and Bornscheuer, U.T., Kinetic resolution of 4-hydroxy-2-ketones catalyzed by a Baeyer-Villiger monooxygenase. Angew. Chem. Int. Ed., 2006,45, 7004. 

Geitner, K., Kirschner, A., Rehdorf, J., Schmidt, M., Mihovilovic, M.D. and Bornscheuer, U.T., Enantioselective kinetic resolution of 3-pheny 1-2-ketones using Baeyer-Villiger monooxygenases. Tetrahedron Asymm., 2007,18, 892. 

Rodriguez, C., de Gonzalo, G., Eraaije, M.W. and Gotor, V., Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases. Tetrahedron Asymm., 2007, 18, 1338. 

A. Rioz-Martinez, A. Cuetos, C. Rodriguez, G. de Gonzalo, 1. Lavandera, M.W. Fraaije, V. Gotor, Dynamic kinetic resolution of alpha-substituted beta-ketoesters catalyzed by Baeyer-Villiger monooxygenases access to enantiopure alpha-hydroxy esters, Angew. Chem.-Int. Ed. 50 (2011) 8387-8390. 

Dynamic kinetic resolution process was also applied to biocatalytic Baeyer-Villiger oxidations. The recombinant E. coli expressing the cyclohexanone monooxygenase from A. calcoaceticus was used for the oxidation of racemic... 

The diastereomeric differentiations in the preceding cases involve physical interactions in chromatography or crystallization. Another possibility is to use a chemical reaction that is fast with one stereoisomer and slow with the other (kinetic resolution). A strain of baker s yeast engineered to express cyclohexanone monooxygenase was used to effect a Baeyer Villiger reaction on a variety of 2-alkylcyclohexanones, an example of which is shown in Equation 3.4 [23]. The ketone and lactone are readily separated by silica gel chromatography. 

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