Enantioselective kinetic resolution of phenylalkyl carboxylic acids using metagenome-derived esterases.

Elena Fernández-Álvaro, Robert Kourist, Julia Winter, Dominique Böttcher, Klaus Liebeton, Christian Naumer, Jürgen Eck, Christian Leggewie, Karl-Erich Jaeger, Wolfgang Streit, Uwe T Bornscheuer

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Enantiomerically pure β-arylalkyl carboxylic acids are important synthetic intermediates for the preparation of a wide range of compounds with biological and pharmacological activities. A library of 83 enzymes isolated from the metagenome was searched for activity in the hydrolysis of ethyl esters of three racemic phenylalkyl carboxylic acids by a microtiter plate-based screening using a pH-indicator assay. Out of these, 20 enzymes were found to be active and were subjected to analytical scale biocatalysis in order to determine their enantioselectivity. The most enantioselective and also enantiocomplementary biocatalysts were then used for preparative scale reactions. Thus, both enantiomers of each of the three phenylalkyl carboxylic acids studied could be obtained in excellent optical purity and high yields.
Original languageEnglish
Pages (from-to)59-64
Number of pages6
JournalMicrobial Biotechnology
Volume3
DOIs
Publication statusPublished - 2010

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Metagenome
Esterases
Carboxylic Acids
Carboxylic acids
Kinetics
Enzymes
Biocatalysis
Biocatalysts
Enantiomers
Enantioselectivity
Hydrolysis
Assays
Esters
Screening
Pharmacology

Keywords

  • Biological Assay Biological Assay: methods Carboxylic Acids Carboxylic Acids: metabolism Esterases Esterases: genetics Esterases: metabolism Kinetics Mass Screening Mass Screening: methods Metagenome Stereoisomerism

Cite this

Enantioselective kinetic resolution of phenylalkyl carboxylic acids using metagenome-derived esterases. / Fernández-Álvaro, Elena; Kourist, Robert; Winter, Julia; Böttcher, Dominique; Liebeton, Klaus; Naumer, Christian; Eck, Jürgen; Leggewie, Christian; Jaeger, Karl-Erich; Streit, Wolfgang; Bornscheuer, Uwe T.

In: Microbial Biotechnology, Vol. 3, 2010, p. 59-64.

Research output: Contribution to journalArticleResearchpeer-review

Fernández-Álvaro, E, Kourist, R, Winter, J, Böttcher, D, Liebeton, K, Naumer, C, Eck, J, Leggewie, C, Jaeger, K-E, Streit, W & Bornscheuer, UT 2010, 'Enantioselective kinetic resolution of phenylalkyl carboxylic acids using metagenome-derived esterases.' Microbial Biotechnology, vol. 3, pp. 59-64. https://doi.org/10.1111/j.1751-7915.2009.00141.x
Fernández-Álvaro, Elena ; Kourist, Robert ; Winter, Julia ; Böttcher, Dominique ; Liebeton, Klaus ; Naumer, Christian ; Eck, Jürgen ; Leggewie, Christian ; Jaeger, Karl-Erich ; Streit, Wolfgang ; Bornscheuer, Uwe T. / Enantioselective kinetic resolution of phenylalkyl carboxylic acids using metagenome-derived esterases. In: Microbial Biotechnology. 2010 ; Vol. 3. pp. 59-64.
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AB - Enantiomerically pure β-arylalkyl carboxylic acids are important synthetic intermediates for the preparation of a wide range of compounds with biological and pharmacological activities. A library of 83 enzymes isolated from the metagenome was searched for activity in the hydrolysis of ethyl esters of three racemic phenylalkyl carboxylic acids by a microtiter plate-based screening using a pH-indicator assay. Out of these, 20 enzymes were found to be active and were subjected to analytical scale biocatalysis in order to determine their enantioselectivity. The most enantioselective and also enantiocomplementary biocatalysts were then used for preparative scale reactions. Thus, both enantiomers of each of the three phenylalkyl carboxylic acids studied could be obtained in excellent optical purity and high yields.

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