Preparation of (2S, 3S)-2,3-Dihydro-3-Hydroxy-2-(4-Methoxyphenyl)-1,5-Benzothiazepin4-(5H)-One by Microbial Conversion
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概要
- 論文の詳細を見る
Microbial production of (2S, 3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(2S, 3S)-DHMB], a key intermediate in the synthesis of diltiazem hydrochloride, was investigated. In the course of the screening of microorganisms for the hydrolysis of 3-acetoxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (AMB), the genera Alcaligenes, Arthrobacter, Bacillus, and Rhodococcus were found to give (2S, 3S)-DHMB from AMB directly at high conversion levels (67-77%) with excellent enantioselectivity [>99% enantiomeric excess (e.e.)]. By using Bacillus sphaericus FERM P-6746,which afforded the highest conversion, the following reaction pathway was postulated : (RS)-2-(4-methoxyphenyl)-1,5-benzothiazepin-3,4(2H, 5H)-dione [(RS)-MBD] was an intermediate, from which the selective reduction subsequently proceeded. This hydrolytic enzyme was induced by AMB. This microbial conversion process provides an efficient method for the synthesis of diltiazem hydrochloride because fewer processes are required and the product can be obtained with a high yield.
- 公益社団法人日本生物工学会の論文
- 1996-06-25
著者
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Shibatani T
Tanabe Seiyaku Co. Ltd. Osaka Jpn
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Shibatani Takeji
Product Technology Development Laboratory Tanabe Seiyaku Co.ltd.
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Shibatani Takeji
Pharmaceutical Developemnt Research Laboratory:tanabe Seiyaku Co. Ltd.
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Nihira Takuya
Department Of Biotechnology Osaka University
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Nakamura Takefumi
Department Of Applied Biological Chemistry Graduate School Of Agricultural And Life Sciences The Uni
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Nishida Takuo
Pharmaceutical Development Research Laboratory Tanabe Seiyaku Co. Ltd.
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Nihira T
International Center For Biotechnology Osaka University
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Ozaki Yasuhiko
Pharmaceutical Development Research Laboratory Tanabe Seiyaku Co. Ltd.
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Machida Ikuko
Pharmaceutica Development Research Laboratory Tanabe Seiyaku Co. Ltd.
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Matsumae H
Tanabe Seiyaku Co. Ltd. Osaka Jpn
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Matsumae Hiroaki
Pharmaceutical Development Research Laboratory Tanabe Seiyaku Co. Ltd.
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Yamada Shinichi
Pharmaceutical Development Research Laboratory Tanabe Seiyaku Co. Ltd.
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