Chemo-biological preparation of the chiral building block (R)-4-acetoxy-2-methyl-1-butanol using Pseudomonas putida |
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Authors: | Youngju Kim Hidenori Watanabe Bieong-Kil Kim Young-Bae Seu |
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Affiliation: | 1. Department of Agricultural Chemistry, The University of Tokyo, Yayoi l-l-l, Bunkyo-ku, Tokyo 113-0032, Japan;2. School of Life Sciences and Biotechnology, Kyungpook National University, 1370, Sangyeokdong, Buk-ku, Daegu 702-701, Republic of Korea |
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Abstract: | In order to develop new methyl substituted chiral building blocks which are useful for the synthesis of methyl branched natural products, the enantioselective bioreduction of an exo-methylene to a methyl group was investigated. 4-Acetoxy-2-methylene-1-butanol 3 was prepared from itaconic acid over four steps and converted to the chiral alcohol (R)-4-acetoxy-2-methyl-1-butanol 4, by growing cells of Pseudomonas putida. The bioconversion achieved a high enantioselectivity (92% ee) and a high chemical yield (65%) within a relatively short reaction time (18–20 h). |
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