X-ray crystallographic proof of electrophilic attack at the pyrimidine/imidazole ring junction in guanosine.
The crystal structure of a novel nucleoside isolated from guanosine/p-methylbenzyl chloride reactions demonstrates linkage between the methylene carbon of the benzyl moiety and carbon-5 of guanosine, and loss of the carbonyl function at carbon-6 of guanosine, to yield 4-(p-methylbenzyl)-5-guanidino-1-beta-D-ribofurasylimidazole. These findings suggest that carbon-5 of guanine in DNA is a potential site of reaction for electrophilic ultimate carcinogens.
D002273:Carcinogens; D006151:Guanosine; D006860:Hydrogen Bonding; D014961:X-Ray Diffraction
D002273:Carcinogens; D006151:Guanosine