Preparation of both enantiomers of methyl 3-benzoyloxypentanoate by enzyme-catalysed hydrolysis of corresponding racemic nitrile and amide

Masahiro Yokoyama, Nori Imai, Takeshi Sugai, Hiromichi Ohta

研究成果: Article査読

26 被引用数 (Scopus)

抄録

Rhodococcus rhodochrous IFO 15564 enantioselectively hydrolysed racemic 3-benzoyloxypentanenitrile and 3-benzoyloxypentanamide to afford (R)-amide and (S)-carboxylic acid with high enantiomeric excess (> 90%). In this reaction, both enantiomers of the starting nitrile were converted to the amide by nitrile hydratase, and amidase-catalysed enantioselective hydrolysis of the amide was responsible for the kinetic resolution. The lack of enantioselectivity of the nitrile hydratase toward the racemic nitrile forms a marked contrast to the case of previously reported highly enantioselective conversion of prochiral 3-benzoyloxypentanedinitrile by this enzyme. Since (R)-amide could be hydrolysed chemically to (R)-carboxylic acid without any loss of its ee, the present microbial kinetic resolution serves as an effective method for preparing both enantiomers of synthetically useful 3-hydroxypentanoic acid derivatives.

本文言語English
ページ(範囲)135-141
ページ数7
ジャーナルJournal of Molecular Catalysis B: Enzymatic
1
3-6
DOI
出版ステータスPublished - 1996 6月

ASJC Scopus subject areas

  • 触媒
  • バイオエンジニアリング
  • 生化学
  • プロセス化学およびプロセス工学

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