HETEROLYTIC C,O-BOND CLEAVAGE OF 4'-NUCLEOTIDE RADICALS

被引:33
作者
GIESE, B [1 ]
ERDMANN, P [1 ]
GIRAUD, L [1 ]
GOBEL, T [1 ]
PETRETTA, M [1 ]
SCHAFER, T [1 ]
VONRAUMER, M [1 ]
机构
[1] UNIV FRIBOURG, INST PHYS CHEM, CH-1700 FRIBOURG, SWITZERLAND
关键词
D O I
10.1016/S0040-4039(00)77005-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photolysis of selenoacetals 7-10 and acylselenides 13 and 14 generates 4'-deoxyribonucleotide radicals. Photocurrent experiments show that radicals with a phosphate group in beta-position give rise to a heterolytical bond cleavage.
引用
收藏
页码:2683 / 2686
页数:4
相关论文
共 17 条
[1]  
BEHRENS G, 1982, Z NATURFORSCH C, V37, P1205
[2]  
COUNDE OY, 1992, TETRAHEDRON LETT, V33, P41
[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]   THE MECHANISM OF ANAEROBIC, RADICAL-INDUCED DNA STRAND SCISSION [J].
GIESE, B ;
BEYRICHGRAF, X ;
BURGER, J ;
KESSELHEIM, C ;
SENN, M ;
SCHAFER, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (12) :1742-1743
[5]   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
[6]   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
[7]   LASER FLASH-PHOTOLYSIS OF CHLORANIL IN SOLUTION [J].
GUERRYBUTTY, E ;
HASELBACH, E ;
PASQUIER, C ;
SUPPAN, P ;
PHILLIPS, D .
HELVETICA CHIMICA ACTA, 1985, 68 (04) :912-918
[8]  
HAGEN U, 1981, ADV RADIAT BIOL, V9, P109
[9]   4'-SUBSTITUTED NUCLEOSIDES .5. HYDROXYMETHYLATION OF NUCLEOSIDE 5'-ALDEHYDES [J].
JONES, GH ;
TANIGUCHI, M ;
TEGG, D ;
MOFFATT, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08) :1309-1317
[10]   CHEMISTRY AND BIOLOGY OF THE ENEDIYNE ANTICANCER ANTIBIOTICS [J].
NICOLAOU, KC ;
DAI, WM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (11) :1387-1416