Highly Regio- and Enantioselective Reduction of 3,5-Dioxocarboxylates

Highly Regio- and Enantioselective Reduction of 3,5-Dioxocarboxylates

Only the keto group in position C‐5 is reduced in the enzymatic reduction of 3,5‐dioxocarboxylates by the alcohol dehydrogenase of Lactobacillus brevis (LBADH; see scheme). The strategy of nature for manipulating β‐keto metabolites inspired the development of a chemoenzymatic approach to virtually e...

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Veröffentlicht in:Angewandte Chemie International Edition 2000-12, Vol.39 (23), p.4306-4308
Hauptverfasser: Wolberg, Michael, Hummel, Werner, Wandrey, Christian, Müller, Michael
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
enzymes
ketones
oxidoreductases
reductions
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Zusammenfassung:Only the keto group in position C‐5 is reduced in the enzymatic reduction of 3,5‐dioxocarboxylates by the alcohol dehydrogenase of Lactobacillus brevis (LBADH; see scheme). The strategy of nature for manipulating β‐keto metabolites inspired the development of a chemoenzymatic approach to virtually enantiopure 3,5‐dihydroxycarboxylate building blocks. The crucial enzymatic step can be performed on an attractively large scale.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20001201)39:23<4306::AID-ANIE4306>3.0.CO;2-G