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

被引：72

作者：

Adam, W

Arnold, MA

Grune, M

Nau, WM

Pischel, U

Saha-Möller, CR

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Univ Basel, Inst Phys Chem, CH-4056 Basel, Switzerland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol017138m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：537 / 540

页数：4

相关论文

共 22 条

[1] Oxidative DNA damage by radicals generated in the thermolysis of hydroxymethyl-substituted 1,2-dioxetanes through the α cleavage of chemiexcited ketones [J].

Adam, W ;

Andler, S ;

Nau, WM ;

Saha-Möller, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3549-3559

[2] Type I and type II photosensitized oxidative modification of 2'-deoxyguanosine (dGuo) by triplet-excited ketones generated thermally from the 1,2-dioxetane HTMD [J].

Adam, W ;

SahaMoller, CR ;

Schonberger, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) :719-723

[3] Photooxidative damage of guanine in DG and DNA by the radicals derived from the α cleavage of the electronically excited carbonyl products generated in the thermolysis of alkoxymethyl-substituted dioxetanes and the photolysis of alkoxyacetones [J].

Adam, W ;

Arnold, MA ;

Saha-Möller, CR .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :597-604

[4] Photooxidation of 8-oxo-7,8-dihydro-2'-deoxyguanosine by thermally generated triplet-excited ketones from 3-(hydroxymethyl)-3,4,4-trimethyl-1,2-dioxetane and comparison with type I and type II photosensitizers [J].

Adam, W ;

SahaMoller, CR ;

Schonberger, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9233-9238

[5] SELECTIVE INADEQUATE - A FAREWELL TO 2D-NMR [J].

BERGER, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1196-1197

[6]

CADET J, 1983, ISRAEL J CHEM, V23, P420

[7] PHOTOSENSITIZED REACTIONS OF NUCLEIC-ACIDS [J].

CADET, J ;

BERGER, M ;

DECARROZ, C ;

WAGNER, JR ;

VANLIER, JE ;

GINOT, YM ;

VIGNY, P .

BIOCHIMIE, 1986, 68 (06) :813-834

[8] DEFINITION OF TYPE-I AND TYPE-II PHOTOSENSITIZED OXIDATION [J].

FOOTE, CS .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1991, 54 (05) :659-659

[9] Removal of hydantoin products of 8-oxoguanine oxidation by the Escherichia coli DNA repair enzyme, FPG [J].

Leipold, MD ;

Muller, JG ;

Burrows, CJ ;

David, SS .

BIOCHEMISTRY, 2000, 39 (48) :14984-14992

[10] The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine [J].

Luo, WC ;

Muller, JG ;

Burrows, CJ .

ORGANIC LETTERS, 2001, 3 (18) :2801-2804