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An Enantiodivergent Trend in Microbial Baeyer−Villiger Oxidations of Functionalized Pentalenones by Recombinant Whole Cells Expressing Monooxygenases from Acinetobacter and Pseudomonas
Author(s) -
Mihovilovic Marko D.,
Müller Bernhard,
Schulze Alexander,
Stanetty Peter,
Kayser Margaret M.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300023
Subject(s) - chemistry , monooxygenase , biotransformation , cyclohexanone , cyclopentanone , pseudomonas , stereochemistry , recombinant dna , biocatalysis , enzyme , organic chemistry , catalysis , biochemistry , bacteria , cytochrome p450 , reaction mechanism , biology , gene , genetics
We have investigated the microbial Baeyer−Villiger oxidations of pentalenones by recombinant whole cells expressing cyclohexanone monooxygenase from Acinetobacter and cyclopentanone monooxygenase from Pseudomonas . The two enzymes display a distinguishable enantiodivergent trend in the biotransformation of some prochiral substrates. A significant influence of the conformation of the fused‐ring system and the polarity of the substituents on the conversion and enantioselectivity of the microbial oxidations was observed and is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)