Resolution of Four K-Region Arene Imines and Mutagenicity of the Optically Pure Aziridines.

Racemic K-region imines of benz[a]anthracene, 7-methylbenz[a]anthracene, chrysene and benzo[a]pyrene (1–4, respectively) have been resolved by high performance liquid chromatography on a column packed with amylose tris(3,5-dimethylphenylcarbamate) on silica gel. The absolute configuration of the resolved aziridines was assigned by comparison of their circular dichromism spectra to those of the corresponding enantiomerically pure arene oxides. The mutagenicity of the enantiomers of the arene imines was investigated using Salmonella typhimurium strains TA98 and TA100. Although all arene imines investigated were potent mutagens, quantitative and qualitative differences in the mutagenic activity were observed between enantiomers.