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Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase |
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| Authors: | Matúš Gajdoš Jendrik Wagner Felipe Ospina Antonia Köhler Dr Martin K M Engqvist Prof Dr Stephan C Hammer |
| Institution: | 1. Faculty of Chemistry, Organic Chemistry and Biocatalysis, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany;2. Department of Biology and Biological Engineering., Chalmers University of Technology, 41296 Gothenburg, Sweden |
| Abstract: | Enantioselective synthesis of chiral alcohols through asymmetric addition of water across an unactivated alkene is a highly sought-after transformation and a big challenge in catalysis. Herein we report the identification and directed evolution of a fatty acid hydratase from Marinitoga hydrogenitolerans for the highly enantioselective hydration of styrenes to yield chiral 1-arylethanols. While directed evolution for styrene hydration was performed in the presence of heptanoic acid to mimic fatty acid binding, the engineered enzyme displayed remarkable asymmetric styrene hydration activity in the absence of the small molecule activator. The evolved styrene hydratase provided access to chiral alcohols from simple alkenes and water with high enantioselectivity (>99 : 1 e.r.) and could be applied on a preparative scale. |
| Keywords: | Alkene Hydration Biocatalysis Directed Evolution Hydratase Stereoselective Catalysis |