Chemoenzymatic Deracemization of Chiral Sulfoxides

The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine‐type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthe...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-07, Vol.57 (31), p.9849-9852
Main Authors: Nosek, Vladimír, Míšek, Jiří
Format: Article
Language:English
Subjects:
biocatalysis
biphasic reactions
chiral sulfoxides
deracemization
Enantiomers
Methionine
oxidoreductases
Reductase
Substrates
Sulfoxides
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Summary:The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine‐type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides. Quality and quantity: The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine‐type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. High ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201805858