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

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.

journal_name

Chem Res Toxicol

authors

Chatgilialoglu C,Bazzanini R,Jimenez LB,Miranda MA

doi

10.1021/tx700282x

subject

Has Abstract

pub_date

2007-12-01 00:00:00

pages

1820-4

issue

12

eissn

0893-228X

issn

1520-5010

journal_volume

20

pub_type

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