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

LILIANA B. JIMENEZ

CHEMICAL RESEARCH IN TOXICOLOGY (WASHINGTON)

American Chemical Society (ACS PUBLICATIONS)

Año: 2007 vol. 20 p. 1820 - 1820

0893-228X

he 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 refs. for the investigation of .gamma.-irradn. of 2´-deoxyguanosine and photolysis of 8-bromo-2´-deoxyguanosine in aq. solns.  The obsd. (5´R)/(5´S) ratio of 8:1 was obtained in both sets of expts.  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.