THE ABSOLUTE STEREOCHEMISTRY OF THE MAJOR TRANS-DIHYDRODIOL ENANTIOMERS FORMED FROM 11-METHYLBENZ[A]ANTHRACENE BY RAT-LIVER MICROSOMES
- 1 January 1982
- journal article
- research article
- Vol. 10 (3) , 205-211
Abstract
Circular dichroism (CD) spectra were determined for the trans-3,4-, 5,6-, 8,9-, and 10,11-dihydrodiols which were formed by incubation of the weakly carcinogenic 11-methylbenz[a]anthracene (11-methyl-BA) with liver microsomes from phenobarbital-pretreated, immature male rats of the Sprague-Dawley strain. These CD spectra were compared with those of the corresponding benz[a]anthracene (BA) trans-dihydrodiol enantiomers of known absolute stereochemistry. The trans-dihydrodiol metabolites of BA and 11-methyl-BA were purified from metabolite mixtures by normal-phase and reversed-phase high-performance liquid chromatography (HPLC). The optically pure (.sbd.)-BA (3R,4R)-dihydrodiol and (+)-BA (3S,4S)-dihydrodiol were resolved via their diastereomeric di(.sbd.)menthoxyacetates by normal-phase HPLC. The CD spectra of the metabolically formed trans-3,4-, 5,6-, 8,9-, and 10,11-dihydrodiols of 11-methyl-BA were closely similar to those of BA(.sbd.)-(3R,4R)-, (+)-(5R,6R)-, (.sbd.)-(8 R,9R)-, and (.sbd.)-(10R,11R)-dihydrodiols. Thus, all the major trans-dihydrodiol enantiomers formed by rat liver microsomes from 11-methyl-BA have R,R absolute configurations.This publication has 23 references indexed in Scilit:
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