Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine

被引：245

作者：

Luo, WC ^{[1
]}

Muller, JG ^{[1
]}

Rachlin, EM ^{[1
]}

Burrows, CJ ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 05期

关键词：

D O I：

10.1021/ol9913643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Further oxidation of the common DNA lesion 8-oxo-7,8-dihydroguanosine by one-electron oxidants such as IrCl62-, Fe(CN)(6)(3-), or SO4- leads to two major products, depending upon reaction conditions. In nucleosides at pH 7, 22 degrees C, the principal product is shown herein to be a spiroiminodihydantoin nucleoside, as a diastereomeric mixture, that can be characterized by NMR, ESI-MS/MS, and independent synthesis.

引用

页码：613 / 616

页数：4

共 26 条

[1] 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
Adam, W
SahaMoller, CR
Schonberger, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) : 9233 - 9238
[2] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY ELECTROCHEMICAL ASSAY FOR MONITORING THE FORMATION OF 8-OXO-7,8-DIHYDROADENINE AND ITS RELATED 2'-DEOXYRIBONUCLEOSIDE
BERGER, M
ANSELMINO, C
MOURET, JF
CADET, J
[J]. JOURNAL OF LIQUID CHROMATOGRAPHY, 1990, 13 (05): : 929 - 940
[3] AN IMPROVED METHOD FOR THE PREPARATION OF THE PHOSPHORAMIDITES OF MODIFIED 2'-DEOXYNUCLEOTIDES - INCORPORATION OF 8-OXO-2'-DEOXY-7H-GUANOSINE INTO SYNTHETIC OLIGOMERS
BODEPUDI, V
IDEN, CR
JOHNSON, F
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1991, 10 (04) : 755 - 761
[4] METHYLENE BLUE-MEDIATED PHOTOOXIDATION OF 7,8-DIHYDRO-8-OXO-2'-DEOXYGUANOSINE
BUCHKO, GW
WAGNER, JR
CADET, J
RAOUL, S
WEINFELD, M
[J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1995, 1263 (01): : 17 - 24
[5] Artifacts associated with the measurement of oxidized DNA bases
Cadet, J
Douki, T
Ravanat, JL
[J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 1997, 105 (10) : 1034 - 1039
[6] Guanine radical cations are precursors of 7,8-dihydro-8-oxo-2'-deoxyguanosine but are not precursors of immediate strand breaks in DNA
Cullis, PM
Malone, ME
MersonDavies, LA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) : 2775 - 2781
[7] 7,8-dihydro-8-oxo-2′-deoxyguanosine residues in DNA are radiation damage "hot" spots in the direct γ radiation damage pathway
Doddridge, ZA
Cullis, PM
Jones, GDD
Malone, ME
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 10998 - 10999
[8] Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine
Duarte, V
Muller, JG
Burrows, CJ
[J]. NUCLEIC ACIDS RESEARCH, 1999, 27 (02) : 496 - 502
[9] Electrochemical and enzymic oxidation of guanosine and 8-hydroxyguanosine and the effects of oxidation products in mice
Goyal, RN
Jain, N
Garg, DK
[J]. BIOELECTROCHEMISTRY AND BIOENERGETICS, 1997, 43 (01): : 105 - 114
[10] Sequence and stacking dependence of 8-oxoguanine oxidation: Comparison of one-electron vs singlet oxygen mechanisms
Hickerson, RP
Prat, F
Muller, JG
Foote, CS
Burrows, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) : 9423 - 9428

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