Enantioselective kinetic resolution of phenylalkyl carboxylic acids using metagenome-derived esterases.
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.
Dept. of Biotechnology and Enzyme Catalysis, Institute of Biochemistry, Greifswald University, Felix-Hausdorff-Str. 4, D-17487 Greifswald, Germany.
Elena
E
Fernández-Álvaro
Robert
R
Kourist
Julia
J
Winter
Dominique
D
Böttcher
Klaus
K
Liebeton
Christian
C
Naumer
Jürgen
J
Eck
Christian
C
Leggewie
Karl-Erich
KE
Jaeger
Wolfgang
W
Streit
Uwe T
UT
Bornscheuer
D001681:Biological Assay / Q000379:methods; D002264:Carboxylic Acids / Q000378:metabolism*; D004950:Esterases / Q000235:genetics* / Q000378:metabolism*; D007700:Kinetics; D008403:Mass Screening / Q000379:methods; D054892:Metagenome; D013237:Stereoisomerism
D002264:Carboxylic Acids; D004950:Esterases
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