(5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: Mechanistic Insights on the 2'-deoxyguanosin-5'-yl Radical Cyclization

Overview

Journal Chem Res Toxicol

Publisher American Chemical Society

Specialty Toxicology

Date 2007 Nov 9

PMID 17988100

Citations 23

Authors

Chryssostomos Chatgilialoglu

Rita Bazzanini

Liliana B Jimenez

Miguel A Miranda

Affiliations

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Abstract

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.

Citing Articles

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