Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative

Shohei Taketomi; Masayoshi Asano; Toshinori Higashi; Mitsuru Shoji; Takeshi Sugai

doi:10.1016/j.molcatb.2012.01.020

Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative

Shohei Taketomi, Masayoshi Asano, Toshinori Higashi, Mitsuru Shoji, Takeshi Sugai

薬科学科

研究成果: Article › 査読

15 被引用数 (Scopus)

抄録

To synthesize (R)-terbutaline hydrochloride, a potent β ₂- adrenoceptor-stimulating agent, asymmetric reduction of a substituted α-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source.

本文言語	English
ページ（範囲）	83-88
ページ数	6
ジャーナル	Journal of Molecular Catalysis B: Enzymatic
巻	84
DOI	https://doi.org/10.1016/j.molcatb.2012.01.020
出版ステータス	Published - 2012 12月

ASJC Scopus subject areas

触媒
バイオエンジニアリング
生化学
プロセス化学およびプロセス工学

文献へのアクセス

10.1016/j.molcatb.2012.01.020

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引用スタイル

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title = "Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative",

abstract = "To synthesize (R)-terbutaline hydrochloride, a potent β 2- adrenoceptor-stimulating agent, asymmetric reduction of a substituted α-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source.",

keywords = "Asymmetric reduction, Hydrolysis, Lipase, Yeast",

author = "Shohei Taketomi and Masayoshi Asano and Toshinori Higashi and Mitsuru Shoji and Takeshi Sugai",

note = "Funding Information: This work was supported by “SORST: Solution-Oriented Research for Science and Technology” of Japan Science and Technology Corporation , and we express our sincere thanks to Professors Keisuke Suzuki, Takashi Matsumoto, Ken Ohmori of Tokyo Institute of Technology. This work was also supported by “High-Tech Research Center” Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and acknowledged with thanks. We acknowledge Novozymes Japan for the generous gift of Novozym 435. M. A. thanks Japan Student Service Organization, for the exemption from repayment upon graduation for graduate school students with outstanding results (2007). ",

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AU - Taketomi, Shohei

AU - Asano, Masayoshi

AU - Higashi, Toshinori

AU - Shoji, Mitsuru

AU - Sugai, Takeshi

N1 - Funding Information: This work was supported by “SORST: Solution-Oriented Research for Science and Technology” of Japan Science and Technology Corporation , and we express our sincere thanks to Professors Keisuke Suzuki, Takashi Matsumoto, Ken Ohmori of Tokyo Institute of Technology. This work was also supported by “High-Tech Research Center” Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and acknowledged with thanks. We acknowledge Novozymes Japan for the generous gift of Novozym 435. M. A. thanks Japan Student Service Organization, for the exemption from repayment upon graduation for graduate school students with outstanding results (2007).

PY - 2012/12

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N2 - To synthesize (R)-terbutaline hydrochloride, a potent β 2- adrenoceptor-stimulating agent, asymmetric reduction of a substituted α-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source.

AB - To synthesize (R)-terbutaline hydrochloride, a potent β 2- adrenoceptor-stimulating agent, asymmetric reduction of a substituted α-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source.

KW - Asymmetric reduction

KW - Hydrolysis

KW - Lipase

KW - Yeast

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