Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase.
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.
Colonna
S
S
Centro CNR and Istituto di Chimica Organica, Facoltà di Farmacia, Milano, Italy. Colonna@mailserver.unimi.it
Gaggero
N
N
Carrea
G
G
Pasta
P
P
Alphand
V
V
Furstoss
R
R
D016954:Acinetobacter calcoaceticus / Q000201:enzymology; D002384:Catalysis; D010105:Oxygenases / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000138:chemical synthesis*
D013451:Sulfonic Acids; C419650:tert-butyl tert-butanethiosulfinate; D010105:Oxygenases; C019961:cyclohexanone oxygenase