Publication: First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases
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Date
2016
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Springer Vienna
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Citation
Rudroff, Florian, Michael J. Fink, Ramana Pydi, Uwe T. Bornscheuer, and Marko D. Mihovilovic. 2016. “First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases.” Monatshefte Fur Chemie 148 (1): 157-165. doi:10.1007/s00706-016-1873-9. http://dx.doi.org/10.1007/s00706-016-1873-9.
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Abstract
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. Graphical abstract
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Keywords
Biotransformation, Baeyer–Villiger oxidation, Taniguchi lactone
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