Volume 24, Issue 14
Preparative Organic Chemistry
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ChemInform Abstract: Enzymatic Enantioselective Ester Hydrolysis by Carboxylesterase NP.

J. W. H. SMEETS

J. W. H. SMEETS

Dep. Bio-Org. Chem., Gist-brocades RPD, 2600 MA Delft, Neth.

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A. P. G. KIEBOOM

A. P. G. KIEBOOM

Dep. Bio-Org. Chem., Gist-brocades RPD, 2600 MA Delft, Neth.

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First published: April 6, 1993

Abstract

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ChemInform Abstract

The enzymatic hydrolysis of a series of racemic carboxylic methyl and ethyl esters by carboxylesterase NP is investigated in order to determine the scope and limitations of this enzyme. Hydrolysis with high enantioselectivity is achieved with several 2-arylpropionates, 2-( aryloxy)propionates, and N-arylalanine esters such as (I), (III), and ( VI) producing propionic acids as (S)-enantiomers and alanine derivatives as (R)-enantiomers. The enzymatic hydrolysis of propionates without 2-aryl substituents occurs at a lower rate without acceptable enantioselectivity. 1-Phenylethyl acetate (VII) is also hydrolyzed enantioselectively. Carboxylesterase NP proved to be a powerful enzyme for kinetic resolution of 2-substituted propionate esters containing an aromatic moiety.

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