Chemoenzymatic Synthesis of Sertraline
A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti‐depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)‐alcohol was efficiently oxidized to an enantiopure (S)‐ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2‐azaadamantane N‐oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.
- 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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Chemoenzymatic Synthesis of Sertraline ; volume:2020 ; number:4 ; year:2020 ; pages:510-513 ; extent:4
European journal of organic chemistry ; 2020, Heft 4 (2020), 510-513 (gesamt 4)
- Creator
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Marx, Lisa
Ríos‐Lombardía, Nicolás
Süss, Philipp
Höhne, Matthias
Morís, Francisco
González‐Sabín, Javier
Berglund, Per
- DOI
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10.1002/ejoc.201901810
- URN
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urn:nbn:de:101:1-2022062307484157953250
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:27 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Marx, Lisa
- Ríos‐Lombardía, Nicolás
- Süss, Philipp
- Höhne, Matthias
- Morís, Francisco
- González‐Sabín, Javier
- Berglund, Per
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