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Short Paper | Special issue | Vol 95, No. 2, 2017, pp.1261-1271
Published online, 21st February, 2017
DOI: 10.3987/COM-16-S(S)89
Asymmetric Biocatalytic Reduction of Cyclic Imines: Design and Application of a Tailor-Made Whole-Cell Catalyst

Nadine Zumbrägel, Dennis Wetzl, Hans Iding, and Harald Gröger*

*Chair of Organic Chemistry I, Faculty of Chemistry, Bielefeld University, Univesitätsstr. 25, 33615 Bielefeld, Germany

Abstract

The design of a recombinant whole-cell catalyst and its utilization in the asymmetric reduction of 1-methyl-3,4-dihydroisoquinoline chosen as a model substrate for cyclic imines is presented. As “designer cells” E. coli cells bearing the two enzymes imine reductase and glucose dehydrogenase (for in situ-cofactor recycling) were constructed, which turned out to be suitable for the asymmetric reduction of 1-methyl-3,4-dihydroisoquinoline at low biocatalyst loading of 2 g/L up to 10 g/L of lyophilized cells, leading to both high conversion and enantioselectivity of >99% ee of the resulting amine. The stoichiometric reducing agent is readily available d-glucose, and a proof of concept for running the reactions at elevated substrate concentration of up to100 mM was demonstrated.