title: First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer-Villiger monooxygenases.
abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer-Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(-)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine.
authors.affiliation: Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163-OC, 1060 Vienna, Austria.
authors.forename: Florian
authors.identifier: 0000-0002-6680-8200
authors.initials: F
authors.lastname: Rudroff
authors.affiliation: Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163-OC, 1060 Vienna, Austria ; Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St, Cambridge, MA 02138 USA.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Fink
authors.affiliation: Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163-OC, 1060 Vienna, Austria.
authors.forename: Ramana
authors.initials: R
authors.lastname: Pydi
authors.affiliation: Department of Biotechnology and Enzyme Catalysis, Institute of Biochemistry, University of Greifswald, 17487 Greifswald, Germany.
authors.forename: Uwe T
authors.identifier: 0000-0003-0685-2696
authors.initials: UT
authors.lastname: Bornscheuer
authors.affiliation: Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163-OC, 1060 Vienna, Austria.
authors.forename: Marko D
authors.initials: MD
authors.lastname: Mihovilovic
keywords: Baeyer–Villiger oxidation; Biotransformation; Taniguchi lactone