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Synthesis of 8‐[ 18 O]hydroxy‐2′‐deoxyguanosine
Author(s) -
Hermanns R. C. A.,
Zomer G.,
Jacquemijns M.,
Stavenuiter J. F. C.,
Westra J. G.,
Teixeira A. J. R.,
Van De Werken G.
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340213
Subject(s) - deoxyguanosine , chemistry , alcohol , sodium , sodium hydride , yield (engineering) , benzyl alcohol , 8 hydroxy 2' deoxyguanosine , catalysis , medicinal chemistry , nuclear chemistry , organic chemistry , dna oxidation , adduct , metallurgy , enzyme , oxidative damage , materials science
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.