Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals
1996; Elsevier BV; Volume: 7; Issue: 2 Linguagem: Inglês
10.1016/0957-4166(96)00040-7
ISSN1362-511X
AutoresStefano Colonna, Nicoletta Gaggero, Giacomo Carrea, Piero Pasta,
Tópico(s)Environmental Chemistry and Analysis
ResumoThe 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.
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