Evolving the Promiscuity of Elizabethkingia meningoseptica Oleate Hydratase for the Regio‐ and Stereoselective Hydration of Oleic Acid Derivatives
Abstract: The addition of water to non‐activated carbon–carbon double bonds catalyzed by fatty acid hydratases (FAHYs) allows for highly regio‐ and stereoselective oxyfunctionalization of renewable oil feedstock. So far, the applicability of FAHYs has been limited to free fatty acids, mainly owing to the requirement of a carboxylate function for substrate recognition and binding. Herein, we describe for the first time the hydration of oleic acid (OA) derivatives lacking this free carboxylate by the oleate hydratase from Elizabethkingia meningoseptica (OhyA). Molecular docking of OA to the OhyA 3D‐structure and a sequence alignment uncovered conserved amino acid residues at the entrance of the substrate channel as target positions for enzyme engineering. Exchange of selected amino acids gave rise to OhyA variants which showed up to an 18‐fold improved conversion of OA derivatives, while retaining the excellent regio‐ and stereoselectivity in the olefin hydration reaction.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Evolving the Promiscuity of Elizabethkingia meningoseptica Oleate Hydratase for the Regio‐ and Stereoselective Hydration of Oleic Acid Derivatives ; volume:58 ; number:22 ; year:2019 ; pages:7480-7484 ; extent:5
Angewandte Chemie / International edition. International edition ; 58, Heft 22 (2019), 7480-7484 (gesamt 5)
- Creator
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Engleder, Matthias
Strohmeier, Gernot A.
Weber, Hansjörg
Steinkellner, Georg
Leitner, Erich
Müller, Monika
Mink, Daniel
Schürmann, Martin
Gruber, Karl
Pichler, Harald
- DOI
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10.1002/anie.201901462
- URN
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urn:nbn:de:101:1-2022073011325242529137
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Engleder, Matthias
- Strohmeier, Gernot A.
- Weber, Hansjörg
- Steinkellner, Georg
- Leitner, Erich
- Müller, Monika
- Mink, Daniel
- Schürmann, Martin
- Gruber, Karl
- Pichler, Harald
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High-Oleic-Sonnenblume als nachwachsender Rohstoff
Stereoselective alkene synthesis
The Poetic Promiscuity of Robert Lowell
Badapple: promiscuity patterns from noisy evidence
Stereoselective synthesis
Stereoselective Synthesis
Maternal Effect on Response of Oleic Acid Content to Temperature in High Oleic Sunflower
Erratum to: Exploiting the promiscuity of imatinib
Evolution of female promiscuity in Passerides songbirds
Prediction of Promiscuity Cliffs Using Machine Learning
Engineering of Methyltransferases: Exploring Their Catalytic Promiscuity
Hydration lubrication
High-Oleic-Sonnenblume als nachwachsender Rohstoff