Spiroiminodihydantoin is a major product in the photooxidation of 2′-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis

Spiroiminodihydantoin is a major product in the photooxidation of 2′-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis
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DOI:
10.1021/ol017138m
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发表时间:
2002-02-21
期刊:
影响因子:
5.2
通讯作者:
Saha-Möller, CR
Saha-Möller, CR
中科院分区:
化学1区
文献类型:
--
作者:
Adam, W;Arnold, MA;Saha-Möller, CR

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Photolysis of hydroxyacetophenone and thermolysis of the corresponding dioxetane afford spiroiminodihydantoin rather than 4,8-dihydro-4hydroxy-8-oxo-2'-deoxyguanosine (4-HO-8-oxodG) through the oxidation of 2'-deoxyguanosine (dG) by triplet-excited hydroxyacetophenone and the peroxyl radicals derived thereof by a cleavage and subsequent oxygen trapping. The structure of the spiroiminodihydantoin is assigned by the SELINQUATE NMR technique, which unequivocally establishes the spirocyclic connectivity.