Asymmetric Bioreduction of Activated Alkenes Using Cloned 12-Oxophytodienoate Reductase Isoenzymes OPR-1 and OPR-3 from Lycopersicon esculentum (Tomato): A Striking Change of Stereoselectivity

Tomato source: 12‐Oxophytodienoate reductase isoenzymes OPR1 and OPR3 from tomato possess a broad substrate spectrum for the asymmetric bioreduction of α,β‐unsaturated enals, enones, dicarboxylic acids, and N‐substituted maleimides (see scheme). Stereocomplementary behavior of both isoenzymes was ob...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-01, Vol.46 (21), p.3934-3937
Hauptverfasser: Hall, Mélanie, Stueckler, Clemens, Kroutil, Wolfgang, Macheroux, Peter, Faber, Kurt
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Sprache:eng
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Zusammenfassung:Tomato source: 12‐Oxophytodienoate reductase isoenzymes OPR1 and OPR3 from tomato possess a broad substrate spectrum for the asymmetric bioreduction of α,β‐unsaturated enals, enones, dicarboxylic acids, and N‐substituted maleimides (see scheme). Stereocomplementary behavior of both isoenzymes was observed in the reduction of a nitroalkene that led to the formation of opposite stereoisomers in high enantiomeric excess.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200605168