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

Gajdos M, Wagner J, Ospina Sánchez F, Köhler A, Engqvist MKM, Hammer S (2023)
Angewandte Chemie International Edition 62(7): e202215093.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Gajdos, MatúsUniBi; Wagner, Jendrik; Ospina Sánchez, FelipeUniBi; Köhler, Antonia; Engqvist, Martin K M; Hammer, StephanUniBi
Abstract / Bemerkung
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. Here we report the identification and directed evolution of a fatty acid hydratase fromMarinitoga hydrogenitoleransfor highly enantioselective hydration of styrenes yielding 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 provides access to chiral alcohols with high enantioselectivity (>99:1 e.r.), yield (up to 98%) and on preparative scale using simple alkenes and water as starting material. © 2022 Wiley-VCH GmbH.
Erscheinungsjahr
2023
Zeitschriftentitel
Angewandte Chemie International Edition
Band
62
Ausgabe
7
Art.-Nr.
e202215093
ISSN
1521-3773
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2967670

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Gajdos M, Wagner J, Ospina Sánchez F, Köhler A, Engqvist MKM, Hammer S. Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase. Angewandte Chemie International Edition. 2023;62(7): e202215093.
Gajdos, M., Wagner, J., Ospina Sánchez, F., Köhler, A., Engqvist, M. K. M., & Hammer, S. (2023). Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase. Angewandte Chemie International Edition, 62(7), e202215093. https://doi.org/10.1002/anie.202215093
Gajdos, Matús, Wagner, Jendrik, Ospina Sánchez, Felipe, Köhler, Antonia, Engqvist, Martin K M, and Hammer, Stephan. 2023. “Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase”. Angewandte Chemie International Edition 62 (7): e202215093.
Gajdos, M., Wagner, J., Ospina Sánchez, F., Köhler, A., Engqvist, M. K. M., and Hammer, S. (2023). Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase. Angewandte Chemie International Edition 62:e202215093.
Gajdos, M., et al., 2023. Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase. Angewandte Chemie International Edition, 62(7): e202215093.
M. Gajdos, et al., “Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase”, Angewandte Chemie International Edition, vol. 62, 2023, : e202215093.
Gajdos, M., Wagner, J., Ospina Sánchez, F., Köhler, A., Engqvist, M.K.M., Hammer, S.: Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase. Angewandte Chemie International Edition. 62, : e202215093 (2023).
Gajdos, Matús, Wagner, Jendrik, Ospina Sánchez, Felipe, Köhler, Antonia, Engqvist, Martin K M, and Hammer, Stephan. “Chiral Alcohols from Alkenes and Water: Directed Evolution of a Styrene Hydratase”. Angewandte Chemie International Edition 62.7 (2023): e202215093.
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