caa a22 4500 467919208 CHVBK 20180406152911.0 cr unu---uuuuu 170328e20060601xx s 000 0 eng 10.1007/s00706-006-0468-2 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0468-2 Microbial Baeyer-Villiger Oxidation of Ketones by Cyclohexanone and Cyclopentanone Monooxygenase - A Computational Rational for Biocatalyst Performance [Elektronische Daten] [Marko D. Mihovilovic, Bernhard Müller, Markus Spina, Arjumand I. Durrani, Peter Stanetty, Georg Dazinger, Karl Kirchner] Summary.: Recombinant Escherichia coli overexpressing Pseudomonas sp. NCIMB 9872 cyclopentanone monooxygenase (CPMO, EC 1.14.13.16) and Acinetobacter sp. NCIMB 9871 cyclohexanone monooxygenase (CHMO, EC 1.14.13.22) have been utilized in whole-cell Baeyer-Villiger biotransformations of prochiral bicycloketones. A significant difference in substrate acceptance and stereoselectivity was observed for bicyclo[3.3.0] and bicyclo[4.3.0] substrates. A plausible mechanism of these transformations was established by means of high level DFT/B3LYP calculations suggesting an essential difference in electronic requirements for a successful enzymatic conversion, which was similarly encountered in recombinant whole-cell mediated biooxidations. Some of the lactones produced in the biocatalytic Baeyer-Villiger oxidation represent key intermediates for the synthesis of indole alkaloids. Springer-Verlag, 2006 Keywords. Biocatalysis nationallicence Recombinant whole-cell biotransformation nationallicence Baeyer-Villiger oxidation nationallicence DFT calculations nationallicence Transition states nationallicence Mihovilovic Marko D. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Müller Bernhard Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Spina Markus Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Durrani Arjumand I. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Stanetty Peter Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Dazinger Georg Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Kirchner Karl Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/6(2006-06-01), 785-794 0026-9247 137:6<785 2006 137 706 https://doi.org/10.1007/s00706-006-0468-2 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0468-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Mihovilovic Marko D. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Müller Bernhard Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Spina Markus Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Durrani Arjumand I. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Stanetty Peter Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Dazinger Georg Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 700 1- Kirchner Karl Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/6(2006-06-01), 785-794 0026-9247 137:6<785 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer