Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase. 2001

S Colonna, and N Gaggero, and G Carrea, and P Pasta, and V Alphand, and R Furstoss
Centro CNR and Istituto di Chimica Organica, Facoltà di Farmacia, Milano, Italy. Colonna@mailserver.unimi.it

Cyclohexanone monooxygenase from Acinetobacter calcoaceticus catalyzes the asymmetric oxidation of tert-butyl disulfide to enantiomerically pure (R)-tert-butyl tert-butanethiosulfinate. Lower enantioselectivities and conversions were observed in the oxidation of i-propyl, n-butyl, p-tolyl tert-butyl disulfides and alkylthiophosphonates.

UI MeSH Term Description Entries
D010105 Oxygenases Oxidases that specifically introduce DIOXYGEN-derived oxygen atoms into a variety of organic molecules. Oxygenase
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013451 Sulfonic Acids Inorganic or organic oxy acids of sulfur which contain the RSO2(OH) radical. Sulfonic Acid,Acid, Sulfonic,Acids, Sulfonic
D016954 Acinetobacter calcoaceticus A species of gram-negative, aerobic bacteria found in soil and water. Although considered to be normally nonpathogenic, this bacterium is a causative agent of nosocomial infections, particularly in debilitated individuals. Micrococcus calcoaceticus,Moraxella calcoacetica,Neisseria winogradskyi

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