CRYSTAL-STRUCTURE OF A CARCINOGEN - NUCLEOSIDE ADDUCT

  • 1 January 1981
    • journal article
    • research article
    • Vol. 41  (6) , 2230-2234
Abstract
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, was prepared and characterized and its structure was determined by X-ray crystallographic techniques. The major structural features are that the adenine and polycyclic aromatic hydrocarbon residues lie nearly perpendicular to one another; 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 the more planar anthracene portion of the hydrocarbon is stacked between adenine residues of other molecules throughout the crystal.