Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system |
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Authors: | Tanja Hischer María Fernández Andrés R Alcántara Winfried Hartmeier |
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Institution: | a Lehrstuhl für Biotechnologie, RWTH Aachen, D-52056 Aachen, Germany b Grupo de Biotransformaciones, Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, E-28040 Madrid, Spain |
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Abstract: | Asymmetric benzoin condensation was performed using recombinant benzaldehyde lyase (BAL) from Pseudomonas fluorescens Biovar I. To enable the conversion of hydrophobic substrates, the enzyme was entrapped in polyvinyl alcohol and suspended in hexane. Compared to the reported application of the biocatalyst in an aqueous phase containing 20% DMSO, the productivity of the resulting gel-stabilised two-phase system was 3-fold better. The entrapment process had an efficiency of >90%, no enzyme or cofactor was lost during reaction or storage. The entrapped enzyme was stable in hexane for 1 week at 4 °C and more than 1 month at −20 °C. Without preceding optimisation the novel benzoins (R)-1,2-di(3-furanyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-thienyl) ethanone, (R)-1,2-di(4-ethoxyphenyl)-2-hydroxyethanone, (R)-1,2-di(3-ethoxyphenyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-tolyl)ethanone, and (R)-1,2-di(benzofuran-2-yl)-2-hydroxyethanone were prepared with yields up to 31.8% and enantiomeric excess >99%. |
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Keywords: | Benzoin condensation Benzaldehyde lyase Entrapment Two-phase system |
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