Multienzymatic preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid |
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Authors: | Patrizia Di Gennaro Silvana Bernasconi Fulvia Orsini Erika Corretto Guido Sello |
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Affiliation: | 1. Dipartimento di Chimica Organica e Industriale, Universita’ degli Studi di Milano, via Venezian 21, 20133 Milano, Italy;2. Dipartimento di Scienze dell’Ambiente e del Territorio, Universita’ di Milano-Bicocca, p.za della Scienza 1, 20126 Milano, Italy |
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Abstract: | The use of two oxidoreductases (an aldoketo reductase from Escherichia coli JM109 and an alcohol dehydrogenase from Lactobacillus brevis) has demonstrated that it is possible to prepare enatiomerically pure diols in a one-pot operation. The reactions were applied to the synthesis of (1R)-1-[3-(hydroxymethyl)phenyl]ethanol and (1S)-1-phenylethane-1,2-diol, using a two-step procedure. The yield is nearly quantitative and the enantiomeric purity is greater than 95%. A third step has been introduced by adding a cell biocatalyst showing dihydrodiol dehydrogenase activity from Pseudomonas fluorescens N3. This allows for the preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid. |
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