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Synfacts 2007(7): 0757-0757  
DOI: 10.1055/s-2007-968634
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Reduction of Activated Olefins Using ‘Old Yellow Enzymes’

Contributor(s): Benjamin List, Daniela Kampen
M. Hall, C. Stueckler, W. Kroutil, P. Macheroux, K. Faber
University of Graz and Graz University of Technology, Austria
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

A biocatalytic asymmetric reduction of olefins 1, which bear an electron-withdrawing group (EWG) has been developed. Isoenzymes OPR1 and OPR3 of 12-oxophytodienoate reductase (OPR) from Lycopersicon esculentum (tomato) mediate chemoselective hydrogenations of α,β-unsaturated aldehydes, (di)ketones, dicarboxylic acids, and imides in high conversions and enantioselectivities. NADH or NADPH is used as cofactor, either in stoichiometric amounts or in combination with different recycling systems. Furthermore, both isoenzymes reduce nitroalkenes 3 to the corresponding nitroalkanes 4 in a stereo­chemically complementary manner.