Enantiomerically pure sulfoxides are excellent chiral auxiliares for asymmetric synthesis and in the preparation of several enantiopure biologically active compounds. We have explored biocatalytic approaches based on the use of heme peroxidases and flavin monooxygenases such as chloroperoxidase and cyclohexanone monooxygenase respectively. By using isolated enzymes or whole-cell bio-transformations, we have prepared alkyl aryl sulfoxides, 1,3-dithioacetal-1-oxides, dialkyl sulfoxides, and thiosulfinates in high enantiomeric excess. An active site model of cyclohexanone monooxygenase has been proposed in order to explain and to predict the absolute configuration of the product.

Enzyme-mediated catalytic asymmetric oxidations / S. Colonna, S. Del Sordo, N. Gaggero, G. Carrea, P. Pasta. - In: HETEROATOM CHEMISTRY. - ISSN 1042-7163. - 13:5(2002), pp. 467-473.

Enzyme-mediated catalytic asymmetric oxidations

S. Colonna
Primo
;
N. Gaggero;
2002

Abstract

Enantiomerically pure sulfoxides are excellent chiral auxiliares for asymmetric synthesis and in the preparation of several enantiopure biologically active compounds. We have explored biocatalytic approaches based on the use of heme peroxidases and flavin monooxygenases such as chloroperoxidase and cyclohexanone monooxygenase respectively. By using isolated enzymes or whole-cell bio-transformations, we have prepared alkyl aryl sulfoxides, 1,3-dithioacetal-1-oxides, dialkyl sulfoxides, and thiosulfinates in high enantiomeric excess. An active site model of cyclohexanone monooxygenase has been proposed in order to explain and to predict the absolute configuration of the product.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/184084
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