The photochemistry of purine components of nucleic acids. II. Photolysis of deoxyguanosine.

ABSTRACT

UV-irradiation (lambda = 254 nm) of liquid aqueous solutions of deoxyguanosine in the presence of oxygen at pH less than 7 causes an intensive degradation of nucleoside. The quantum yield estimated from A254 decrease for the reaction mixture was found to be 1.5X10(-4) at doses to 150 E/mole. The rate of A254 decrease was found to grow with increasing doses. The structures of the products isolated from the reaction mixture after irradiation suggest that one of the ways of deoxyguanosine degradation is a breakdown of a purine cycle without splitting of N-glycoside bond. Simultaneously another type of photoinduced modification of guanine nucleus takes place, which is followed by appearance of free 2-deoxyribose. Deoxyguanosine degradation in both directions is kinetically one-step process proceeding with comparable quantum yields of approximately 1X10(-4).