Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600

Kento Asami, Takuya Machida, Sonna Jung, Kengo Hanaya, Mitsuru Shoji, Takeshi Sugai

Research output: Contribution to journalLetter

7 Citations (Scopus)

Abstract

To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield.

Original languageEnglish
Pages (from-to)106-109
Number of pages4
JournalJournal of Molecular Catalysis B: Enzymatic
Volume97
DOIs
Publication statusPublished - 2013 Jan 1

Keywords

  • Hydrolysis
  • Lipase
  • Reduction
  • Whole-cell biocatalyst
  • Yeast

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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