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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.

作者信息

Adam Waldemar, Arnold Markus A, Grüne Matthias, Nau Werner M, Pischel Uwe, Saha-Möller Chantu R

机构信息

Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.

出版信息

Org Lett. 2002 Feb 21;4(4):537-40. doi: 10.1021/ol017138m.

DOI:10.1021/ol017138m
PMID:11843585
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.

摘要

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