Elaboration on the access to (S)-4-(4-methylbenzyl)oxy-3-hydroxybutanenitrile, a key intermediate for statins, by combining the kinetic resolution of racemate and the recycle of undesired enantiomer

Maki Sakamoto, Manabu Hamada, Toshinori Higashi, Mitsuru Shoji, Takeshi Sugai

研究成果: Article

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High enantioselectivity (E 94) was observed in Candida antarctica lipase B-catalyzed hydrolysis of the corresponding acetate of racemic title compound. The reaction rate of the slow (S)-isomer was effectively suppressed by lowering the reaction temperature from 25°C to 5°C, to allow a five times increase of the enantioselectivity. The ee of the (S)-isomer, reached 97.8% at the reasonable conversion (52%) as the unreacted recovery, and the repetition of the enzymatic reaction provided pure enantiomer. The undesired (R)-isomer was oxidized with IBX and reduced with whole-cell biocatalysis with Candida floricola JCM 9439 to (S)-isomer (63.2% ee), which serves as the enantiomerically enriched substrate for further lipase-catalyzed resolution. The combination of total processes provided over 50% yield of the pure (S)-isomer, exceeding the theoretical limit for the enantiomeric resolution of racemate.

元の言語English
ページ(範囲)96-100
ページ数5
ジャーナルJournal of Molecular Catalysis B: Enzymatic
64
発行部数1-2
DOI
出版物ステータスPublished - 2010 6 1

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ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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