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Crystal Structure of a Carcinogen:Nucleoside Adduct¹

The Institute for Cancer Research, The Fox Chase Cancer Center, Philadelphia, Pennsylvania 19111 [H. L. C., J. P. G.], and Chemical Carcinogenesis Program, Frederick Cancer Research Center, Frederick, Maryland 21701 [R. C. M., W. R. H., A. D.]

The product of reaction between the carcinogen, 7-bromomethyl-12-methylbenz[a]anthracene, and 2'-deoxyadenosine, i.e., N⁶-(12-methylbenz[a]anthracenyl-7-methyl)deoxyadenosine, has been prepared and characterized, and its structure has been determined by X-ray crystallographic techniques. The major structural features are: (a) the adenine and polycyclic aromatic hydrocarbon residues lie nearly perpendicular to one another; (b) the conformation about the glycosidic bond is syn, rather than anti, and an internal hydrogen bond between the deoxyribose 5'-hydroxyl group and N(3) of the adenine residue is present; and (c) the more planar anthracene portion of the hydrocarbon is stacked between adenine residues of other molecules throughout the crystal.

¹ This research was supported by Grant BC-242 from the American Cancer Society; USPHS Grants CA-10925, CA-22780, CA-06927, and RR-05539 from the NIH; an appropriation from the Commonwealth of Pennsylvania; and Contract N01-CO-75380 with the National Cancer Institute, NIH, Bethesda, Md. 20205.

² To whom requests for reprints should be addressed.

Received 11/14/80. Accepted 2/26/81.

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