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STEREOSELECTIVITY OF ENZYMATIC AND CHEMICAL OXYGENATION OF SULFUR-ATOMS IN 2-METHYL-1,3-BENZODITHIOLE
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UNSPECIFIED (1992) STEREOSELECTIVITY OF ENZYMATIC AND CHEMICAL OXYGENATION OF SULFUR-ATOMS IN 2-METHYL-1,3-BENZODITHIOLE. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 114 (23). pp. 8772-8777. ISSN 0002-7863.
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Abstract
S-Monooxygenation of 2-methyl-1,3-benzodithiole, to yield cis- and trans-2-methyl-1,3-benzodithiole 1-oxide, has been studied as a new stereochemical probe using achiral and chiral chemical oxidants and enzymes from microbial and animal sources. Chemical oxidants showed a preference for trans S-oxide formation, and this preference was enhanced in the presence of a chiral matrix. The ability of pure enzymes to stereodifferentiate between geminal lone pairs on a prochiral sulfur atom, or geminal sulfur atoms on a prochiral carbon atom, has been observed. Thus, intact fungal and bacterial oxidations showed a marked selectivity (87-96%) for formation of the cis S-oxide isomers. In addition, highly purified hog liver and rabbit lung flavin-containing monooxygenases showed a marked preference for formation of the cis S-oxide and the pro-R sulfur atom. Other monooxygenase-catalyzed sulfoxidations of 2-methyl-1,3-benzodithiole, including cytochrome P-450 2B1 (P450PB-B), showed a markedly lower stereoselectivity.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | ||||
Publisher: | AMER CHEMICAL SOC | ||||
ISSN: | 0002-7863 | ||||
Official Date: | 4 November 1992 | ||||
Dates: |
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Volume: | 114 | ||||
Number: | 23 | ||||
Number of Pages: | 6 | ||||
Page Range: | pp. 8772-8777 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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