Microbial Baeyer-Villiger oxidation: stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution

Marko D Mihovilovic; Florian Rudroff; Alexander Winninger; Toni Schneider; Frank Schulz; Manfred T Reetz

doi:10.1021/ol0601040

Microbial Baeyer-Villiger oxidation: stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution

Org Lett. 2006 Mar 16;8(6):1221-4. doi: 10.1021/ol0601040.

Authors

Marko D Mihovilovic¹, Florian Rudroff, Alexander Winninger, Toni Schneider, Frank Schulz, Manfred T Reetz

Affiliation

¹ Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria. mmihovil@pop.tuwien.ac.at

PMID: 16524308
DOI: 10.1021/ol0601040

Abstract

[reaction: see text] An array of random mutants of cyclohexanone monooxygenase (CHMO) from Acinetobacter sp. NCIMB 9871 was screened against a library of structurally diverse ketones for modifications in the substrate acceptance profile and stereopreference of the enzymatic Baeyer-Villiger biooxidation. While the set of mutant biocatalysts was initially evolved for the enantiocomplementary oxidation of 4-hydroxycyclohexanone, improved and/or divergent stereoselectivities were observed for several substrates. In addition, expanded substrate acceptance to facilitate biotransformation of sterically demanding ketones was found.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acinetobacter / enzymology*
Acinetobacter / genetics
Combinatorial Chemistry Techniques
Ketones / chemical synthesis*
Ketones / chemistry
Models, Molecular
Oxidation-Reduction
Oxygenases / genetics
Oxygenases / metabolism*
Stereoisomerism

Substances

Ketones
Oxygenases
cyclohexanone oxygenase