Abstract
The stereochemical properties of ligands that form covalent adducts with DNA have profound effects on their biochemical functions. Differing absolute configurations of substituents about chiral carbon atoms can lead to strikingly different conformations when such stereoisomeric compounds bind to DNA. The environmental chemical carcinogen, benzo[a]pyrene (BP), provides a remarkable example of such stereochemical effects. Metabolic activation of benzo[a]pyrene leads to a pair of enantiomers, (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene and its (−)-(7S,8R,9R,10S) mirror-image, known as (+)- and (−)-anti-BPDE. Both (+)- and (−)-anti-BPDE react with the amino group of adenine in DNA via trans epoxide opening, yielding a pair of stereochemically distinct trans-anti-benzo[a]pyrenyl adducts, whose possible role in chemical carcinogenesis is of great interest. High-resolution NMR solution studies (Schurter et al. Biochemistry 1995, 34, 1364−75; Yeh et al. Biochemistry 1995, 34, 135...
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