Biocatalytic production of (S)-4-bromo-3-hydroxybutyrate and structurally related chemicals and their applications |
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Authors: | Hiroyuki Asako Masatoshi Shimizu Nobuya Itoh |
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Affiliation: | (1) Organic Synthesis Research Laboratory, Sumitomo Chemical Co., Ltd., 1-98, Kasugade-naka 3-chome, Konohana-ku Osaka, 554-8558, Japan;(2) Department of Biotechnology, Faculty of Engineering (Biotechnology Research Center), Toyama Prefectural University, Kurokawa 5180, Imizu Toyama, 939-0398, Japan |
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Abstract: | The enzymatic production of (S)-4-bromo-3-hydroxybutyrate has been poorly studied compared with (S)-4-chloro-3-hydroxybutyrate. This can be attributed to the toxicity of bromide for biocatalysis. Recently, we isolated cDNA that encodes Penicillium citrinum β-keto ester reductase (KER) and the gene that encodes Leifsonia sp. alcohol dehydrogenase, which catalyzes the reduction of methyl 4-bromo-3-oxobutyrate to methyl (S)-4-bromo-3-hydroxybutyrate with high optical purity and productivity and expressed them in Escherichia coli. Moreover, protein engineering was performed using error-prone PCR-based random mutagenesis to improve the thermostability and enantioselectivity of KER. This review focuses on the establishment of a novel biotechnological process for the production of (S)-4-bromo-3-hydroxybutyrate using E. coli transformants. This process is suitable for industrial production of (S)-4-bromo-3-hydroxybutyrate, an intermediate for statin compounds. |
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Keywords: | (S)-4-Bromo-3-hydroxybutyrate Intermediate for statin compounds Enzymatic production Aldo-keto reductase Penicillium citrinum Alcohol dehydrogenase Leifsonia sp. |
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