Mechanistic studies in the radical induced DNA strand cleavage - Formation and reactivity of the radical cation intermediate

被引：26

作者：

Glatthar, R

Spichty, M

Gugger, A

Batra, R

Damm, W

Mohr, M

Zipse, H

Giese, B

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

TETRAHEDRON | 2000年 / 56卷 / 25期

关键词：

4 '-DNA radical; radical cation; regioselective addition; calculations; solvent effect; VBCM;

D O I：

10.1016/S0040-4020(00)00335-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to understand the heterolytic cleavage of 4'-DNA radical 1 and the regioselective attack of nucleophiles at the intermediate DNA radical cation 3, the chemistry of model radical 8 was studied. It turned out that the heterolytic cleavage in water is favored over homolysis because of the effective solvation of the ions 9 and 10. The regioselectivity of the nucleophilic attack at radical cation 10 can be explained with the valence bond configuration mixing (VBCM) model. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4117 / 4128

页数：12

共 62 条

[1] The photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .11. Involving (R)-(+)-alpha-terpineol and (R)-(+)-limonene, substituting on 1,4-dicyanobenzene
Arnold, DR
Conner, DA
McManus, KA
Bakshi, PK
Cameron, TS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (04): : 602 - 612
[2] RADICAL IONS IN PHOTOCHEMISTRY .20. THE PHOTOCHEMICAL NUCLEOPHILE-OLEFIN COMBINATION, AROMATIC-SUBSTITUTION REACTION .2. METHANOL - CYCLIC OLEFINS, 1,4-DICYANOBENZENE
ARNOLD, DR
SNOW, MS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (12): : 3012 - 3026
[3] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .12. Factors controlling the regiochemistry of the reaction with alcohol as the nucleophile
Arnold, DR
Chan, MSW
McManus, KA
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (11): : 2143 - 2166
[4] Calculations of isotropic hyperfine coupling constants of organic radicals. An evaluation of semiempirical, Hartree-Fock, and density functional methods
Batra, R
Giese, B
Spichty, M
Gescheidt, G
Houk, KN
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (47) : 18371 - 18379
[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[6] Chemistry of β-(acyloxy)alkyl and β-(phosphatoxy)alkyl radicals and related species:: Radical and radical ionic migrations and fragmentations of carbon-oxygen bonds
Beckwith, ALJ
Crich, D
Duggan, PJ
Yao, QW
[J]. CHEMICAL REVIEWS, 1997, 97 (08) : 3273 - 3312
[7] INFLUENCE OF PROTONATION OR ALKYLATION OF PHOSPHATE GROUP ON ESR-SPECTRA AND ON RATE OF PHOSPHATE ELIMINATION FROM 2-METHOXYETHYL PHOSPHATE 2-YL RADICALS
BEHRENS, G
KOLTZENBURG, G
RITTER, A
SCHULTEFROHLINDE, D
[J]. INTERNATIONAL JOURNAL OF RADIATION BIOLOGY, 1978, 33 (02) : 163 - 171
[8] RADICAL IONS IN PHOTOCHEMISTRY .15. THE PHOTOSUBSTITUTION REACTION BETWEEN DICYANOBENZENES AND ALKYL OLEFINS
BORG, RM
ARNOLD, DR
CAMERON, TS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (09): : 1785 - 1802
[9] DETERMINING ATOM-CENTERED MONOPOLES FROM MOLECULAR ELECTROSTATIC POTENTIALS - THE NEED FOR HIGH SAMPLING DENSITY IN FORMAMIDE CONFORMATIONAL-ANALYSIS
BRENEMAN, CM
WIBERG, KB
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (03) : 361 - 373
[10] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction, part 15. Investigations involving fluoride anion as the nucleophile and the effect of fluorine substitution on the relative stability of the reaction intermediates
Chan, MSW
Arnold, DR
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1997, 75 (12) : 1810 - 1819

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