Modification of DNA Following Activation of Benzo(a)pyrene

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Modification of  N2 of Guanine
This is the most frequent damage occurring to DNA following metabolic activation of benzo(a)pyrene.  The structure presented here was solved using NMR techniques (B. Feng, A. Gorin, A. Kolbanovskiy, B. E. Hingerty, N. E. Geacintov, S. Broyde, D. J. Patel, Biochemistry, 36, 13780, (1997)), and illustrates the disruption caused to the DNA structure by reaction of N² of a guanine residue with benzo(a)pyrene-7,8-diol-9,10-epoxide.  The modified base is prevented form forming normal base-pairing interactions for steric reasons, and is displaced into the minor groove.  The benzo(a)pyrene unit is located inside the helix, and is intercalated between the unmodified bases.