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

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

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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.

Original languageEnglish
Pages (from-to)4367-4370
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number23
DOIs
Publication statusPublished - Jun 4 1999

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Ema, T., Okada, R., Fukumoto, M., Jittani, M., Ishida, M., Furuie, K., Yamaguchi, K., Sakai, T., & Utaka, M. (1999). Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols. Tetrahedron Letters, 40(23), 4367-4370. https://doi.org/10.1016/S0040-4039(99)00750-9