The asymmetric oxidation of 2-substituted dithianes, dithiolanes and oxathiolanes catalyzed by cyclohexanone monooxygenase (CMO) has been examined. The introduction of substituents at the C-2 causes a decrease of the e.e. with the exception of 2-benzoyl-1,3-dithiane monosulfoxide (90% e.e). With 2-monosubstituted dithioacetals CMO yields preferentially or exclusively the trans diastereoisomer. The binding of the 1,3-dithioacetals at the active site of the enzyme is not only controlled by the sterical hindrance of the substituents in position 2 but also by the configuration at C-2. The stereoselectivity of CMO has been compared with that reported for microsomal flavin and cytochrome P-450 monooxygenases.
Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals / S. Colonna, N. Gaggero, G. Carrea, P. Pasta. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 7:2(1996), pp. 565-570.
Titolo: | Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals |
Autori: | COLONNA, STEFANO (Primo) GAGGERO, NICOLETTA (Secondo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1996 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/0957-4166(96)00040-7 |
Appare nelle tipologie: | 01 - Articolo su periodico |