Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols

Ema Tadashi; Ryoichi Okada; Minoru Fukumoto; Masahito Jittani; Mikiko Ishida; Kenji Furuie; Kunihiro Yamaguchi; Takashi Sakai; Masanori Utaka

doi:10.1016/S0040-4039(99)00750-9

Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols

Ema Tadashi, Ryoichi Okada, Minoru Fukumoto, Masahito Jittani, Mikiko Ishida, Kenji Furuie, Kunihiro Yamaguchi, Takashi Sakai, Masanori Utaka

研究成果 › 査読

14 被引用数 (Scopus)

抄録

In the subtilisin-catalyzed transesterications of a variety of secondary alcohols, the (S)-enantiomers were acylated faster. Kinetic measurements indicated that the enantioselectivily originates from chiral discrimination in the transition state. A transition-state model capable of explaining the S-preference of subtilisin toward secondary alcohols has been proposed.

本文言語	English
ページ（範囲）	4367-4370
ページ数	4
ジャーナル	Tetrahedron Letters
巻	40
号	23
DOI	https://doi.org/10.1016/S0040-4039(99)00750-9
出版ステータス	Published - 6月 4 1999

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4039(99)00750-9

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author = "Ema Tadashi and Ryoichi Okada and Minoru Fukumoto and Masahito Jittani and Mikiko Ishida and Kenji Furuie and Kunihiro Yamaguchi and Takashi Sakai and Masanori Utaka",

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T1 - Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols

AU - Tadashi, Ema

AU - Okada, Ryoichi

AU - Fukumoto, Minoru

AU - Jittani, Masahito

AU - Ishida, Mikiko

AU - Furuie, Kenji

AU - Yamaguchi, Kunihiro

AU - Sakai, Takashi

AU - Utaka, Masanori

PY - 1999/6/4

Y1 - 1999/6/4

N2 - In the subtilisin-catalyzed transesterications of a variety of secondary alcohols, the (S)-enantiomers were acylated faster. Kinetic measurements indicated that the enantioselectivily originates from chiral discrimination in the transition state. A transition-state model capable of explaining the S-preference of subtilisin toward secondary alcohols has been proposed.

AB - In the subtilisin-catalyzed transesterications of a variety of secondary alcohols, the (S)-enantiomers were acylated faster. Kinetic measurements indicated that the enantioselectivily originates from chiral discrimination in the transition state. A transition-state model capable of explaining the S-preference of subtilisin toward secondary alcohols has been proposed.

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U2 - 10.1016/S0040-4039(99)00750-9

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols

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