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

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)135-141
Number of pages7
JournalJournal of Molecular Catalysis B: Enzymatic
Volume1
Issue number3-6
Publication statusPublished - 1996 Jun

Fingerprint

Nitriles
Enantiomers
Amides
Hydrolysis
Enzymes
Carboxylic Acids
amidase
Carboxylic acids
Rhodococcus
Kinetics
Enantioselectivity
Derivatives
Acids
nitrile hydratase

Keywords

  • 3-Hydroxypentanoate derivatives
  • Amidase
  • Kinetic resolution
  • Nitrile hydratase
  • Rhodococcus rhodochrous

ASJC Scopus subject areas

  • Biochemistry
  • Catalysis
  • Process Chemistry and Technology

Cite this

Preparation of both enantiomers of methyl 3-benzoyloxypentanoate by enzyme-catalysed hydrolysis of corresponding racemic nitrile and amide. / Yokoyama, Masahiro; Imai, Nori; Sugai, Takeshi; Ohta, Hiromichi.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 1, No. 3-6, 06.1996, p. 135-141.

Research output: Contribution to journalArticle

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AB - 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.

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