The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes |
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| Authors: | Herman Ziffer Kuninbu Kabuto DT Gibson VM Kobal Donald M Jerina |
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| Institution: | Laboratory of Chemical Physics, National Institute of Arthritis, Metabolism and Digestive Diseases, National Institutes of Health, Bethesda, MD 20014, U.S.A.;Department of Microbiology, University of Texas, Austin, TX 78712, U.S.A.;Laboratory of Chemistry, National Institute of Arthritis, Metabolism and Digestive Diseases, National Institutes of Health, Bethesda, MD 20014, U.S.A. |
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| Abstract: | The absolute stereochemistry of a series of 3-substituted cis-dihydrodiols obtained by microbial oxidation of toluene, ethylbenzene, chlorobenzene, and biphenyl has been assigned from chemical and spectrophotometric studies. ?-Halogenated toluenes also have been investigated as substrates in these oxidations, and the corresponding cis-dihydrodiols isolated. Implications from the observation that some of the cis-dihydrodiols are racemic are discussed. Oxidation of an olefin, (±)-3-methylcyclohexene, by these microorganisms leads only to cis-diols whose absolute stereochemistry about the hydroxyl-bearing carbons is the same as that found for the cis-dihydrodiols formed from the aromatic substrates. |
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