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

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

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4367-4370
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(99)00750-9
Publication status	Published - Jun 4 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00750-9

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abstract = "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.",

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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EP - 4370

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

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

Abstract

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