- Bacterial dioxygenase-catalysed dihydroxylation and chemical resolution routes to enantiopure cis-dihydrodiols of chrysene
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Biotransformation of the environmental pollutant chrysene 1 by resting cells of a mutant strain (B8/36) of the soil bacterium Sphingomonas yanoikuyae produces (+)-cis-3,4-dihydroxy-3,4-dihydrochrysene 4 which has been assigned (3S,4R) absolute configuration by stereochemical correlation with (-)-(3S,4R)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrochrysene 6. Both cis-3,4-diol 6 and cis-1,2-dihydroxy-1,2,3,4-tetrahydrochrysene 12 are obtained in enantiopure form after chromatographic separation of the individual bis(2-methoxy-2-phenyl-2-trifluoromethylacetyl) (bis-MTPA) diastereoisomers of compound 6 and the MTPA diastereoisomers of bromohydrin 19, respectively, followed by hydrolysis. A new general synthetic route to cis-dihydrodiols, from the corresponding cis-tetrahydrodiol cyclic carbonates, is used to obtain both racemic and enantiopure forms of the bay-region diol 4, and the non-bay region diol 5. 1H NMR and CD spectra of the cis- and trans-dihydrodiols of chrysene are described.
- Boyd, Derek R.,Sharma, Narain D.,Agarwal, Rajiv,Resnick, Sol M.,Schocken, Mark J.,Gibson, David T.,Sayer, Jane M.,Yagi, Haruhiko,Jerina, Donald M.
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p. 1715 - 1723
(2007/10/03)
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- Synthesis of the Enantiomeric Bay-Region Diol Epoxides of Benzanthracene and Chrysene
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Both trans-3,4-dihydroxy-3,4-dihydrobenzanthracene and trans-1,2-dihydroxy-1,2-dihydrochrysene are known proximate carcinogens of their respective hydrocarbons.The present study describes the synthesis of their (+)- and (-)-enantiomers as well as the d
- Yagi, Haruhiko,Vyas, Kamlesh P.,Tada, Masao,Thakker, Dhiren R.,Jerina, Donald M.
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p. 1110 - 1117
(2007/10/02)
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- Synthesis, Resolution and Racemization Studies of 1,2-Epoxy-1,2-dihydrochrysene
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(+)-1,2-Epoxy-1,2-dihydrochrysene, a major initial mammalian metabolite of chrysene, has been synthesised and assigned the configuration (1R,2S)- Kinetic studies on the spontaneous thermal racemization of (+)-1,2-epoxy-1,2-dihydrochrysene gave a barrier t
- Boyd, Derek R.,Greene, Ruth M. E.
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p. 1535 - 1540
(2007/10/02)
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