DNA damaged by Benzopyrene-diol-epoxide

Benzopyrene is a chemical found in cigarette smoke.  Benzopyrene is converted to Benzopyrene-diol-epoxide in the body, which can randomly insert itself into the grooves of DNA.  Once bound in the groove, DNA is not able to be replicated or transcribed effectively.  This may cause mutations in daughter cells or unfavorable effects on gene expression.

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Yeh, H. J., Sayer, J. M., Liu, X., Altieri, A. S., Byrd, R. A., Lakshman, M. K., Yagi, H., Schurter, E. J., Gorenstein, D. G., Jerina, D. M.:

NMR solution structure of a nonanucleotide duplex with a dG mismatch opposite a 10S adduct derived from trans addition of a deoxyadenosine N6-amino group to (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene: an unusual syn glycosidic torsion angle at the modified dA.

Biochemistry 34 pp. 13570 (1995)