Abstract

In the project 'Oxidative DNA Damage' the first aim is to develop a method for the quantification of 8-Hydroxy-2'-deoxyguanosine (oh8dG). For the method development standard material is needed. In this report the applied route for the synthesis of oh8dG is described. 8-Hydroxy-2'-deoxyguanosine was synthesised starting from 2'-deoxyguanosine (dG) in three steps. In the first step dG was brominated at the C-8 position, resulting in 8-bromo-2'-deoxyguanosine (8-Br-dG). 8-Br-dG was converted into 8-benzyloxy-2'-deoxyguanosine (8-benzyloxy-dG) by treatment of 8-Br-dG with the sodium salt of benzylalcohol. Finally 8-benzyloxy-dG was hydrogenated resulting in 8-hydroxy-2'-deoxyguanosine (oh8dG). Compared to dG, the overall yield of the total procedure was approximately 4%. The total amount produced is 5 mg oh8dG with an estimated purity of 93%, based on HPLC analysis.