Shifting the equilibrium of a biocatalytic cascade synthesis to enantiopure epoxides using anion exchangers |
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| Authors: | Joerg H Schrittwieser Iván Lavandera Birgit Seisser Barbara Mautner Jeffrey H Lutje Spelberg Wolfgang Kroutil |
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| Institution: | 1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria;2. Research Centre Applied Biocatalysis c/o Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria;3. Julich Chiral Solutions, a Codexis company, Prof.-Rehmstrasse 1, 52428 Jülich, Germany |
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| Abstract: | Hydroxide-loaded anion exchangers have been successfully employed to shift the equilibrium of a one-pot, two-step, two-enzyme cascade reaction affording enantiopure epoxides starting from prochiral α-chloroketones. The α-chloroketones were asymmetrically reduced employing an alcohol dehydrogenase and then transformed further to the corresponding epoxides employing halohydrin dehalogenases. Each epoxide enantiomer could be obtained with up to 93% conversion in enantiomerically pure form (>99% ee). In contrast to previous studies the amount of hydride donor (2-propanol) could be reduced due to favoured halohydrin formation in the reduction of α-chloroketones. |
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