X-ray crystallographic proof of electrophilic attack at the pyrimidine/imidazole ring junction in guanosine |
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| Authors: | Carrell, H.L. Zacharias, D.E. Glusker, J.P. Moschel, R.C. Hudgins, W.R. Dipple, A. |
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| Affiliation: | 1The Institute for Cancer Research, The Fox Chase Cancer Center Philadelphia, PA 19111, USA
2Chemical Carcino-genesis Program, NCI-FCRF Frederick, MD 21701, USA |
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| Abstract: | The crystal structure of a novel nucleoside isolated from guanosine/p-methylbenzylchloride reactions demonstrates linkage between the methylenecarbon of the benzyl moiety and carbon-5 of guanosine, and lossof the carbonyl function at carbon-6 of guanosine, to yield4-(p-methylbenzyl)-5-guanidino-1-ß-D-ribofuranosylimidazole.These findings suggest that carbon-5 of guanine in DNA is apotential site of reaction for electrophilic ultimate carcinogens. |
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