(5′S)- and (5′R)-5′,8-cyclo-2′-deoxyguanosine:: Mechanistic insights on the 2′-deoxyguanosin-5′-yl radical cyclization

被引：47

作者：

Chatgilialoglu, Chryssostomos ^{[1
]}

Bazzanini, Rita ^{[1
]}

Jimenez, Liliana B. ^{[1
,2
]}

Miranda, Miguel A. ^{[2
]}

机构：

[1] Consiglio Nazl Ricerche, ISOF, I-40129 Bologna, Italy

[2] Univ Politecn Valencia, UPV CSIC, Inst Tecnol Quim, E-46022 Valencia, Spain

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 2007年 / 20卷 / 12期

关键词：

D O I：

10.1021/tx700282x

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

The two diastereomeric forms (5'S) and (5'R) of 5',8-cyclo-2'-deoxyguanosine have been synthesized and fully characterized. They have been used as references for the investigation of gamma-irradiation of 2'-deoxyguanosine and photolysis of 8-bromo-2'-deoxyguanosine in aqueous solutions. The observed (5'R)/(5'S) ratio of 8:1 was obtained in both sets of experiments. The mechanism of the cyclization reaction is discussed in some detail, and the diastereomeric outcome is rationalized in terms of favorable hydrogen-bonded structures in the pro-(5'R) conformation.

引用

页码：1820 / 1824

页数：5

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