THE MECHANISM OF ANAEROBIC, RADICAL-INDUCED DNA STRAND SCISSION

被引：73

作者：

GIESE, B

BEYRICHGRAF, X

BURGER, J

KESSELHEIM, C

SENN, M

SCHAFER, T

机构：

[1] Departement Chemie der, Universität, Basel, CH-4056

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1993年 / 32卷 / 12期

关键词：

D O I：

10.1002/anie.199317421

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

After selective generation of the mononucleotide radical 1, the formation and reactions of radical cation 2 could be studied. Trapping with allyl alcohol, which is known to trap both cations and radicals, gave primarily the bicyclic product 3. With methanol several intermediates could be trapped, the hydrolysis products of which correspond to DNA cleavage products. 4′‐Deoxyribonucleotide radicals are proposed as intermediates in radical‐induced DNA strand scission. ℗  P(O)(OEt)2, b  thymine. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1742 / 1743

页数：2

相关论文

共 14 条

[1] SOLVENT EFFECTS ON THE COMPETITIVE BETA-SCISSION AND HYDROGEN-ATOM ABSTRACTION REACTIONS OF THE CUMYLOXYL RADICAL - RESOLUTION OF A LONG-STANDING PROBLEM [J].

AVILA, DV ;

BROWN, CE ;

INGOLD, KU ;

LUSZTYK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :466-470

[2]

BEHRENS G, 1982, Z NATURFORSCH C, V37, P1205

[3] FREE-RADICAL MECHANISMS INVOLVED IN THE FORMATION OF SEQUENCE-DEPENDENT BISTRANDED DNA LESIONS BY THE ANTITUMOR ANTIBIOTICS BLEOMYCIN, NEOCARZINOSTATIN, AND CALICHEAMICIN [J].

DEDON, PC ;

GOLDBERG, IH .

CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (03) :311-332

[4] MODEL STUDIES ON THE RADICAL INDUCED DNA STRAND CLEAVAGE [J].

GIESE, B ;

BURGER, J ;

KANG, TW ;

KESSELHEIM, C ;

WITTMER, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7322-7324

[5] MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].

GOLDBERG, IH .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198

[6] FAST HYDROLYSIS OF ALKYL RADICALS WITH LEAVING GROUPS IN THE BETA-POSITION [J].

KOLTZENBURG, G ;

BEHRENS, G ;

SCHULTEFROHLINDE, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7311-7312

[7]

MASTRYUKOVA TA, 1959, ZH OBSHCH KHIM+, V29, P2178

[8] CHEMISTRY AND BIOLOGY OF THE ENEDIYNE ANTICANCER ANTIBIOTICS [J].

NICOLAOU, KC ;

DAI, WM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (11) :1387-1416

[9]

NICOLAOU KC, 1991, ANGEW CHEM, V103, P1453

[10] SYNTHESIS OF 4'-CYANOTHYMIDINE AND ANALOGS AS POTENT INHIBITORS OF HIV [J].

OYANG, C ;

WU, HY ;

FRASERSMITH, EB ;

WALKER, KAM .

TETRAHEDRON LETTERS, 1992, 33 (01) :37-40