Synthesis of 8-[18O]hydroxy-2′-deoxyguanosine

✍ Scribed by R. C. A. Hermanns; G. Zomer; M. Jacquemijns; J. F. C. Stavenuiter; J. G. Westra; A. J. R. Teixeira; G. Van De Werken

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: French
• Weight: 390 KB
• Volume: 34
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580340213

✦ Synopsis

Abstract

8‐[^18^O]Hydroxy‐2′‐deoxyguanosine was synthesized starting from 8‐bromo‐2′‐deoxyguanosine and the sodium salt of [^18^O]benzyl alcohol, resulting in the intermediate 8‐[^18^O]benzyloxy‐2′‐deoxyguanosine. Subsequent reduction by catalytic transfer hydrogenation, yielded the desired product 8‐[^18^O]hydroxy‐2′‐deoxyguanosine.

8‐Bromo‐2′‐deoxyguanosine was synthesized from 2′‐deoxyguanosine by treatment with Br~2~. The sodium salt of [^18^O]benzyl alcohol was prepared by treatment of ethyl benzimidate hydrochloride with H~2~^18^O (95%), LiAlH~4~ and sodium hydride. Starting from H~2~^18^O the overall yield of 8‐[^18^O]hydroxy‐2′‐deoxyguanosine was approximately 4%. The isotopic purity was calculated to be 93.4 atom% based on GC‐MS measurements. The chemical purity and the isotopic purity comply with the planned application, namely as internal standard for the determination of 8‐hydroxy‐2′‐deoxyguanosine by GC‐MS.