Microbial Baeyer-Villiger oxidation: stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution.
[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.
Mihovilovic
Marko D
MD
Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria. mmihovil@pop.tuwien.ac.at
Rudroff
Florian
F
Winninger
Alexander
A
Schneider
Toni
T
Schulz
Frank
F
Reetz
Manfred T
MT
D000150:Acinetobacter / Q000201:enzymology* / Q000235:genetics; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000235:genetics / Q000378:metabolism*; D013237:Stereoisomerism
D007659:Ketones; D010105:Oxygenases; C019961:cyclohexanone oxygenase