Analysis of Oxidative DNA Damage, Part I: Synthesis of the standard material 8-hydroxy-2'-deoxyguanosine

Hermanns RCA; Zomer G; Stavenuiter JFC; Westra G; Visser T; van de Werken G

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Authors

Hermanns RCA
Zomer G
Stavenuiter JFC
Westra G
Visser T
van de Werken G

Type

Report

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Title

Analysis of Oxidative DNA Damage, Part I: Synthesis of the standard material 8-hydroxy-2'-deoxyguanosine

Translated Title

[Synthese van 8-hydroxy-2'-deoxyguanosine.]

Publiekssamenvatting

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.<br>