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• W2105328609 abstract "ABSTRACT The degradation of 7,12-dimethylbenz[ a ]anthracene (DMBA), a carcinogenic polycyclic aromatic hydrocarbon, by cultures of Mycobacterium vanbaalenii PYR-1 was studied. When M. vanbaalenii PYR-1 was grown in the presence of DMBA for 136 h, high-pressure liquid chromatography (HPLC) analysis showed the presence of four ethyl acetate-extractable compounds and unutilized substrate. Characterization of the metabolites by mass and nuclear magnetic resonance spectrometry indicated initial attack at the C-5 and C-6 positions and on the methyl group attached to C-7 of DMBA. The metabolites were identified as cis -5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz[ a ]anthracene (DMBA cis -5,6-dihydrodiol), trans -5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz[ a ]anthracene (DMBA trans -5,6-dihydrodiol), and 7-hydroxymethyl-12-methylbenz[ a ]anthracene, suggesting dioxygenation and monooxygenation reactions. Chiral stationary-phase HPLC analysis of the dihydrodiols showed that DMBA cis -5,6-dihydrodiol had 95% 5 S ,6 R and 5% 5 R ,6 S absolute stereochemistry. On the other hand, the DMBA trans -5,6-dihydrodiol was a 100% 5 S ,6 S enantiomer. A minor photooxidation product, 7,12-epidioxy-7,12-dimethylbenz[ a ]anthracene, was also formed. The results demonstrate that M. vanbaalenii PYR-1 is highly regio- and stereoselective in the degradation of DMBA." @default.
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• W2105328609 date "2003-07-01" @default.
• W2105328609 modified "2023-10-03" @default.
• W2105328609 title "Regio- and Stereoselective Metabolism of 7,12-Dimethylbenz[ <i>a</i> ]anthracene by <i>Mycobacterium vanbaalenii</i> PYR-1" @default.
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• W2105328609 doi "https://doi.org/10.1128/aem.69.7.3924-3931.2003" @default.
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