Rapid PaperMicrobial Oxygenation of Organo-metallic Bissulfides Leading to Formation of Planar Chirality and C2 Symmetry |
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Authors: | Yoshimitsu Yamazaki Kuniaki Hosono |
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Institution: | Fermentation Research Institute, Agency of Industrial Science and Technology, Tsukuba, Ibaraki 305, Japan |
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Abstract: | 1,2-Bis(methylthiomethyl)ferrocene (3) was oxidized by Corynebacterium equi IFO 3730 to give monosulfoxide 4 in two diastereomeric forms with (1S,2R,SS) and (1S,2R,RS) configurations in a ratio of 4:1, while 1,1′-bis(methylthiomethyl)ferrocene (5) was oxidized by Penicillium frequentans IFO 5692 to (R)-monosulfoxide 6 and then preferentially to (R,R)-bissulfoxide 7. Thus, the bacterial monooxygenase generated specific planar chirality in the metallocenic monosulfoxide, and the fungal enzyme formed C2 symmetry in the bissulfoxide. |
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