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Baeyer-Villiger oxidations catalyzed by engineered microorganisms: Enantioselective synthesis of d-valerolactones with functionalized chains

Wang, Shaozhao; Chen, Gang; Kayser, Margaret M; Iwaki, Hiroaki; Lau, Peter C.K; Hasegawa, Yoshie
June 2002
Canadian Journal of Chemistry;Jun2002, Vol. 80 Issue 6, p613
Academic Journal
Cyclohexanone monooxygenase (CHMO) from Acinetobacter sp NCIMB 9871 expressed in baker's yeast and in E. coli and cyclopentanone monooxygenase (CPMO) from Comamonas (previously Pseudomonas) sp. NCIMB 9872 expressed in E. coli are new bioreagents for Baeyer-Villiger oxidations. These engineered microorganisms, requiring neither biochemical expertise nor equipment beyond that found in chemical laboratories, were evaluated as reagents for Baeyer-Villiger oxidations of cyclopentanones substituted at the 2-position with polar and nonpolar chains suitable for further modifications. Two such functionalized substrates that can be transformed into highly enantiopure lactones were identified. The performance and the potential of these bioreagents are discussed.Key words: enantioselective Baeyer-Villiger oxidations, biotransformations, cyclohexanone monooxygenase, cyclo pentanone monooxygenase, engineered baker's yeast, recombinant E. coli, optically pure 2-substituted cyclopentanones, optically pure lactones.La monooxygénase de la cyclohexanone (« CHMO ») obtenue à partir d'Acinetobacter sp NCIMB 9871 extraite de la levure pâtissière et d'E. coli et la monooxygénase de la cyclopentanone (« CPMO ») de Comamonas (antérieurement Pseudomonas) sp. NCIMB 9872 extraite d'E. coli sont les nouveaux bioréactifs pour les oxydations de Baeyer-Villiger. Ces microorganismes, qui ne nécessitent ni expertise biochimique ni équipement supplémentaire par rapport à ce que l'on retrouve dans les laboratoires chimiques, ont été évalués comme réactifs pour des oxydations de Baeyer-Villiger de cyclopentanones substituées en position 2 par des chaînes polaires ainsi que non polaires susceptibles d'être modifiées ultérieurement. On a identifié deux de ces substrats fonctionnalisés qui peuvent être éventuellement transformés en lactones de grande pureté énantiomérique. On discute de la performance et du potentiel de ces bioréactifs.Mots clés : oxydations de Baeyer-Villiger, biotransformations, monooxygénase de la cyclohexanone, monooxygénase de la cyclopentanone, levure pâtissière, E. coli recombinant, cyclopentanone substituée en position 2 optiquement pure, lactones optiquement pures.[Traduit par la Rédaction]


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