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 language | English |
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Pages (from-to) | 135-141 |
Number of pages | 7 |
Journal | Journal of Molecular Catalysis B: Enzymatic |
Volume | 1 |
Issue number | 3-6 |
DOIs | |
Publication status | Published - 1996 Jun |
Keywords
- 3-Hydroxypentanoate derivatives
- Amidase
- Kinetic resolution
- Nitrile hydratase
- Rhodococcus rhodochrous
ASJC Scopus subject areas
- Catalysis
- Bioengineering
- Biochemistry
- Process Chemistry and Technology