Enzymatically Enantioselective Hydrolysis of Prochiral 1,3-Diacyloxyglycerol Derivatives

Yoshihiko Yasohara, Noriyuku Kizaki, Kenji Miyamoto, Junzo Hasegawa, Takehisa Ohashi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An enzymatically enantioselective ester hydrolysis of prochiral 1,3-diacyloxy-2-substituted-2-propanol to chiral 1-acyloxy-2,3-propanediol was studied. The (R)-monoester was prepared by selection of a suitable lipase and alkyl chain length of the substrate diester. Lipase D from Rhizopus delemer gave (R)-1-isobutyryloxy-2-(2,4-difluorophenyl)-2,3-propanediol with 97%ee and 87% yield at 15°C and pH 5.5. The (R)-monoester is a key intermediate of azole antifungal agents.

Original languageEnglish
Pages (from-to)2044-2049
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume65
Issue number9
DOIs
Publication statusPublished - 2001 Sep 1

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Keywords

  • Enantioselective hydrolysis
  • Glycerol derivative
  • Lipase

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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