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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

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  • Financial support by BASF AG (Ludwigshafen) is gratefully acknowledged. We would like to thank H. Ehammer, E. Pointner, T. Pavkov, and K. Zangger for their excellent technical assistance.

Abstract

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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.

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