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
Organic Letters2002Vol. 4(4), pp. 537–540
Citations Over TimeTop 10% of 2002 papers
Abstract
[reaction: see text] Photolysis of hydroxyacetophenone and thermolysis of the corresponding dioxetane afford spiroiminodihydantoin rather than 4,8-dihydro-4-hydroxy-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 alpha cleavage and subsequent oxygen trapping. The structure of the spiroiminodihydantoin is assigned by the SELINQUATE NMR technique, which unequivocally establishes the spirocyclic connectivity.
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