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Resolution and absolute configuration of 7,12-dimethylbenz[a]anthracene 5,6-epoxide enantiomers.

Abstract：

:The enantiomers of 7,12-dimethylbenz[a]anthracene (DMBA) 5,6-epoxide were directly resolved by normal-phase high-performance liquid chromatography with an ionically bonded chiral stationary phase. The absolute configurations of the resolved enantiomers were determined by comparison of circular dichroism spectra of the methanolysis products formed from the epoxide enantiomers with that of a DMBA trans-5,6-dihydrodiol enantiomer of known absolute stereochemistry. DMBA 5R,6S-epoxide is hydrated by rat liver microsomal epoxide hydrolase predominantly (95%) to a 5S,6S-dihydrodiol. The results indicate that the 5S,6S-dihydrodiol formed from the metabolism of DMBA by microsomes prepared from the livers of 3-methylcholanthrene-treated rats is predominantly derived from a 5R,6S-epoxide intermediate.

journal_name

Biochem Biophys Res Commun

journal_title

Biochemical and biophysical research communications

authors

Mushtaq M,Weems HB,Yang SK

doi

10.1016/0006-291x(84)90573-4

subject

Has Abstract

pub_date

1984-12-14 00:00:00

pages

539-45

issue

2

eissn

0006-291X

issn

1090-2104

pii

0006-291X(84)90573-4

journal_volume

125

pub_type

杂志文章

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