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In the γ-radiolysis of deoxygenated N 2 O-saturated aqueous solutions of thymidine (10 -3  M, room temperature, dose rate 4· 10 18  eV/g.h., dose 6.7 10 17 -3.3 • 10 18  eV/g) the following products (G-values in parentheses) have been identified : 2,5-dideoxy-pentos-4-ulose (1) (0.01), 2,4-dideoxy-pentodialdose (2) (0.02), 2,4-dideoxy-pentos-3-ulose (3) (0.03), 2,3-dideoxy-pentos-4-ulose (4) (0.01), 2-deoxy-pentos-4-ulose (5) (0.1), 2-deoxyribonic acid (6) (0.02) and thymine (8) ( ≤ 0.2). In the presence of oxygen (N 2 O/O 2  80/20 v/v saturated) products 1-4 are absent, G (5) = 0.2, G (6) = 0.07 and G (8) ≤ 0.4. Furthermore, 2-deoxy-tetrodialdose (7) which is absent in deoxygenated solution is formed with a G-value of 0.03. Mechanisms are proposed to account for the scission of the N-glycosidic linkage. Product 6 is thought to be due to a primary OH radical attack at C-1′ of the sugar moiety, 8 arises from an attack at C-3′, 1, 4 and 5 from an attack at C-4′, and 2 and 7 from an attack at C-5′.

zeitschrift für naturforschung b

Radiation Chemistry of DNA Model Compounds, IX. Carbohydrate Products in the γ-Radiolysis of Thymidine in Aqueous Solution. The Radical-Induced Scission of the N-Glycosidic Bond