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.
Multienzymatic preparation of (-)-[3-(oxiran-2-yl)phenyl]methanol and (-)-3-(oxiran-2-yl)benzoic acid / G. Sello, S. Bernasconi, F. Orsini, P. Di Gennaro. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 20:5(2009 May 25), pp. 563-565. [10.1016/j.tetasy.2009.03.023]
Multienzymatic preparation of (-)-[3-(oxiran-2-yl)phenyl]methanol and (-)-3-(oxiran-2-yl)benzoic acid
G. SelloPrimo
;S. BernasconiSecondo
;F. OrsiniPenultimo
;
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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