Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

Chihiro Hiraoka; Masaaki Matsuda; Yuya Suzuki; Shigeo Fujieda; Mina Tomita; Ken ichi Fuhshuku; Rika Obata; Shigeru Nishiyama; Takeshi Sugai

doi:10.1016/j.tetasy.2006.12.013

Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

Chihiro Hiraoka, Masaaki Matsuda, Yuya Suzuki, Shigeo Fujieda, Mina Tomita, Ken ichi Fuhshuku, Rika Obata, Shigeru Nishiyama, Takeshi Sugai

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S,5S)-2,6-dimethyl-3,5-heptanediol 12a.

Original language	English
Pages (from-to)	3358-3367
Number of pages	10
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	24
DOIs	https://doi.org/10.1016/j.tetasy.2006.12.013
Publication status	Published - 2006 Dec 27

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones",

abstract = "Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S,5S)-2,6-dimethyl-3,5-heptanediol 12a.",

author = "Chihiro Hiraoka and Masaaki Matsuda and Yuya Suzuki and Shigeo Fujieda and Mina Tomita and Fuhshuku, {Ken ichi} and Rika Obata and Shigeru Nishiyama and Takeshi Sugai",

note = "Funding Information: We thank Professors Tadashi Ema, Okayama University, Mitsuru Abo, the University of Tokyo, and Jon D. Stewart, University of Florida, for valuable suggestions on this work, and Amano Enzyme Inc. for lipase PS-C. This work was accomplished as the 21st century COE Program (KEIO LCC), also supported by {\textquoteleft}SORST: Solution-Oriented Research for Science and Technology{\textquoteright} of Japan Science and Technology Corporation, and we express our sincere thanks to Professors Keisuke Suzuki, Takashi Matsumoto and Dr. Ken Ohmori of Tokyo Institute of Technology.",

year = "2006",

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doi = "10.1016/j.tetasy.2006.12.013",

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AU - Hiraoka, Chihiro

AU - Matsuda, Masaaki

AU - Suzuki, Yuya

AU - Fujieda, Shigeo

AU - Tomita, Mina

AU - Fuhshuku, Ken ichi

AU - Obata, Rika

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

N1 - Funding Information: We thank Professors Tadashi Ema, Okayama University, Mitsuru Abo, the University of Tokyo, and Jon D. Stewart, University of Florida, for valuable suggestions on this work, and Amano Enzyme Inc. for lipase PS-C. This work was accomplished as the 21st century COE Program (KEIO LCC), also 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 and Dr. Ken Ohmori of Tokyo Institute of Technology.

PY - 2006/12/27

Y1 - 2006/12/27

N2 - Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S,5S)-2,6-dimethyl-3,5-heptanediol 12a.

AB - Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S,5S)-2,6-dimethyl-3,5-heptanediol 12a.

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Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

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