Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase ; day:11 ; month:01 ; year:2023 ; extent:7
Angewandte Chemie ; (11.01.2023) (gesamt 7)
- Urheber
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Gajdoš, Matúš
Wagner, Jendrik
Ospina, Felipe
Köhler, Antonia
Engqvist, Martin K. M.
Hammer, Stephan C.
- DOI
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10.1002/ange.202215093
- URN
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urn:nbn:de:101:1-2023011214184976433045
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:24 MESZ
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Beteiligte
- Gajdoš, Matúš
- Wagner, Jendrik
- Ospina, Felipe
- Köhler, Antonia
- Engqvist, Martin K. M.
- Hammer, Stephan C.
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Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols
Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols
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Chemoenzymatic Synthesis of Chiral Alcohols Relevant to Pharmaceutical Industry
Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis
Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols
Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols
Stereodivergent Synthesis of Chiral Amino Alcohols by Copper(I) Catalyst
Coupling metal and whole-cell catalysis to synthesize chiral alcohols
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