The cascade use of enzymatic activities allows for the preparation of enantiomerically pure epoxides. In particular, using whole-cell biocatalysts we can prepare both (−)-[3-(oxiran-2-yl)phenyl]methanol and (−)-3-(oxiran-2-yl)benzoic acid in one-pot, two or three steps procedure. The yield is quantitative and enantiomeric purity greater than 95%. The selected biocatalysts contain a styrene monoxygenase from Pseudomonas fluorescens ST and a naphthalene dihydrodiol dehydrogenase from P. fluorescens N3, cloned and expressed in Escherichia coli
Sello, G., Bernasconi, S., Orsini, F., DI GENNARO, P. (2009). Multienzymatic preparation of 3-(oxiran-2-yl)phenylmethanol and 3-(oxiran-2-yl)benzoic acid. TETRAHEDRON-ASYMMETRY, 20(5), 563-565 [10.1016/j.tetasy.2009.03.023].
Multienzymatic preparation of 3-(oxiran-2-yl)phenylmethanol and 3-(oxiran-2-yl)benzoic acid
DI GENNARO, PATRIZIA
2009
Abstract
The cascade use of enzymatic activities allows for the preparation of enantiomerically pure epoxides. In particular, using whole-cell biocatalysts we can prepare both (−)-[3-(oxiran-2-yl)phenyl]methanol and (−)-3-(oxiran-2-yl)benzoic acid in one-pot, two or three steps procedure. The yield is quantitative and enantiomeric purity greater than 95%. The selected biocatalysts contain a styrene monoxygenase from Pseudomonas fluorescens ST and a naphthalene dihydrodiol dehydrogenase from P. fluorescens N3, cloned and expressed in Escherichia coli
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