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Microbial Baeyer–Villiger Oxidation of Prochiral Polysubstituted Cyclohexanones by Recombinant Whole‐Cells Expressing Two Bacterial Monooxygenases
Author(s) -
Mihovilovic Marko D.,
Rudroff Florian,
Grötzl Birgit,
Stanetty Peter
Publication year - 2005
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.200400676
Subject(s) - chemistry , monooxygenase , stereoselectivity , stereochemistry , cyclohexanone , biocatalysis , lipophilicity , cyclopentanone , bioconversion , substrate (aquarium) , enzyme , organic chemistry , combinatorial chemistry , cytochrome p450 , catalysis , reaction mechanism , fermentation , oceanography , geology
The microbial Baeyer–Villiger oxidation of prochiral 3,5‐dimethylcyclohexanones bearing various functionalities with recombinant E. coli cells overexpressing cyclohexanone monooxygenase from Acinetobacter sp . NCIMB 9871 and cyclopentanone monooxygenase from Comamonas sp. NCIMB 9872 has been investigated. A distinct difference in substrate specificity and stereoselectivity of the two enzymes was observed, and enantiocomplementary products were obtained in some cases. The biocatalytic systems enabled access to chiral lactones as valuable intermediates for the total synthesis of various natural compounds. Substituents with varying lipophilicity and hybridization have been prepared by a diastereoselective synthetic route and subsequently bio‐transformed for the investigation of conformational and electronic effects on the biooxidation,. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)