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 journalArticlepeer-review

14 Citations (Scopus)


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
Issue number23
Publication statusPublished - Jun 4 1999

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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