Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase ; day:11 ; month:01 ; year:2023 ; extent:7
Angewandte Chemie / International edition. International edition ; (11.01.2023) (gesamt 7)

Creator: Gajdoš, Matúš
Wagner, Jendrik
Ospina, Felipe
Köhler, Antonia
Engqvist, Martin K. M.
Hammer, Stephan C.

DOI: 10.1002/anie.202215093

URN: urn:nbn:de:101:1-2023011214142167274488

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:25 AM CEST

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Associated

Gajdoš, Matúš
Wagner, Jendrik
Ospina, Felipe
Köhler, Antonia
Engqvist, Martin K. M.
Hammer, Stephan C.

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