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Whole-Cell-Catalyzed Multiple Regio- and Stereoselective Functionalizations in Cascade Reactions Enabled by Directed Evolution

MPS-Authors

Li,  Aitao
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ilie,  Adriana
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Sun,  Zhoutong
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lonsdale,  Richard
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Li, A., Ilie, A., Sun, Z., Lonsdale, R., Xu, J.-H., & Reetz, M. T. (2016). Whole-Cell-Catalyzed Multiple Regio- and Stereoselective Functionalizations in Cascade Reactions Enabled by Directed Evolution. Angewandte Chemie International Edition, 55(39), 12026-12029. doi:10.1002/anie.201605990.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-9AD1-E
Abstract
Biocatalytic cascade reactions using isolated stereoselective enzymes or whole cells in one-pot processes lead to value-added chiral products in a single workup. The concept has been restricted mainly to starting materials and intermediate products that are accepted by the respective wild-type enzymes. In the present study, we exploited directed evolution as a means to create E. coli whole cells for regio- and stereoselective cascade sequences that are not possible using man-made catalysts. The approach is illustrated using P450-BM3 in combination with appropriate alcohol dehydrogenases as catalysts in either two-, three-, or four-step cascade reactions starting from cyclohexane, cyclohexanol, or cyclohexanone, respectively, leading to either (R,R)-, (S,S)-, or meso-cyclohexane-1,2-diol. The one-pot conversion of cyclohexane into (R)- or (S)-2-hydroxycyclohexanone in the absence of ADH is also described.