One‐pot Chemoenzymatic Synthesis of Chiral 1,3‐Diols Using an Enantioselective Aldol Reaction with Chiral Zn2+ Complex Catalysts and Enzymatic Reduction Using Oxidoreductases with Cofactor Regeneration |
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Authors: | Shotaro Sonoike Toshinari Itakura Dr Masanori Kitamura Prof Shin Aoki |
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Institution: | 1. Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda 278‐8510 (Japan), Fax: (+81)?4‐7121‐3670;2. Center for Technologies against Cancer, Tokyo University of Science, 2641 Yamazaki, Noda 278‐8510 (Japan) |
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Abstract: | We previously reported on enantioselective aldol reactions of acetone and some aldehydes catalyzed by chiral Zn2+ complexes of L ‐prolyl‐pendant 12]aneN4 (L ‐ZnL1) and L ‐valyl‐pendant 12]aneN4 (L ‐ZnL2) in aqueous solution. Here, we report on the one‐pot chemoenzymatic synthesis of chiral 1,3‐diols in an aqueous solvent system at room temperature by a combination of enantioselective aldol reactions catalyzed by Zn2+ complexes of L ‐ and D ‐phenylalanyl‐pendant 12]aneN4 (L ‐ZnL3 and D ‐ZnL3) and the successive enantioselective reduction of the aldol products using oxidoreductases with the regeneration of the NADH (reduced form of nicotinamine adenine dinucleotide) cofactor. The findings indicate that all four stereoisomers of 1,3‐diols can be produced by appropriate selection of a chiral Zn2+‐complex and an oxidoreductase commercially available from the “Chiralscreen OH” kit. |
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Keywords: | aldol reaction asymmetric catalysis biocatalysis water chemistry zinc |
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