Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases

作者: Cristina Rodríguez , Gonzalo de Gonzalo , Marco W. Fraaije , Vicente Gotor

DOI: 10.1016/J.TETASY.2007.05.033

关键词:

摘要: Abstract A set of racemic cyclic and linear ketones, as well 2-phenylpropionaldehyde, were tested substrates in the enzymatic Baeyer–Villiger oxidation catalyzed by two monooxygenases: phenylacetone monooxygenase (PAMO) 4-hydroxyacetophenone (HAPMO). Excellent enantioselectivites (E > 200) can be obtained kinetic resolution processes depending on substrate structure reaction conditions. The parameters affecting biocatalytic properties these enzymes also studied, order to establish a deeper understanding novel biocatalysts.

参考文章(48)
Marı́a C Gutiérrez, Véronique Alphand, Roland Furstoss, Microbiological transformations 52.: Biocatalysed Baeyer–Villiger oxidation of 1-indanone derivatives Journal of Molecular Catalysis B-enzymatic. ,vol. 21, pp. 231- 238 ,(2003) , 10.1016/S1381-1177(02)00227-8
D. Enders, H. Eichenauer, U. Baus, H. Schubert, K.A.M. Kremer, Asymmetric syntheses via metalated chiral hydrazones : Overall enantioselective α-alkylation of acyclic ketones Tetrahedron. ,vol. 40, pp. 1345- 1359 ,(1984) , 10.1016/S0040-4020(01)82420-0
Marko Mihovilovic, Enzyme Mediated Baeyer-Villiger Oxidations Current Organic Chemistry. ,vol. 10, pp. 1265- 1287 ,(2006) , 10.2174/138527206777698002
Stefano Colonna, Nicoletta Gaggero, Stefano Colonna, Giacomo Carrea, Piero Pasta, Oxidation of organic cyclic sulfites to sulfates: a new reaction catalyzed by cyclohexanone monooxygenase Chemical Communications. pp. 415- 416 ,(1998) , 10.1039/A707749A
Christopher M. Clouthier, Margaret M. Kayser, Increasing the enantioselectivity of cyclopentanone monooxygenase (CPMO) : profile of new CPMO mutants Tetrahedron-asymmetry. ,vol. 17, pp. 2649- 2653 ,(2006) , 10.1016/J.TETASY.2006.10.001
Marco W. Fraaije, Andrea Mattevi, Flavoenzymes: diverse catalysts with recurrent features Trends in Biochemical Sciences. ,vol. 25, pp. 126- 132 ,(2000) , 10.1016/S0968-0004(99)01533-9
Marko D. Mihovilovic, Bernhard Müller, Peter Stanetty, Monooxygenase‐Mediated Baeyer−Villiger Oxidations European Journal of Organic Chemistry. ,vol. 2002, pp. 3711- 3730 ,(2002) , 10.1002/1099-0690(200211)2002:22<3711::AID-EJOC3711>3.0.CO;2-5
Nanne M. Kamerbeek, Dick B. Janssen, Willem J. H. van Berkel, Marco W. Fraaije, Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts Advanced Synthesis & Catalysis. ,vol. 345, pp. 667- 678 ,(2003) , 10.1002/ADSC.200303014
Gianluca Ottolina, Silvia Bianchi, Barbara Belloni, Giacoma Carrea, Bruno Danieli, First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase Tetrahedron Letters. ,vol. 40, pp. 8483- 8486 ,(1999) , 10.1016/S0040-4039(99)01780-3