105929-27-9

Upstream product

• 13389-03-2 8-bromo-2'-deoxyguanosine 

Relevant academic research and scientific papers

Radiation-induced formation of purine 5′,8-cyclonucleosides in isolated and cellular DNA: High stereospecificity and modulating effect of oxygen

The present work is aimed at gaining conclusive mechanistic insights into the radiation-induced formation of the 5′R and 5′S diastereomers of both adenine and guanine 5′,8-cyclo-2′-deoxyribonucleosides, with emphasis on the delineation of the inhibitory effect of O2 in isolated and cellular DNA. The levels of purine 5′,8-cyclo-2′- deoxyribonucleosides as assessed by HPLC-MS/MS were found to decrease steadily with the increase of O2 concentration, the 5′,8-cyclo-2′- deoxyguanosine being produced more efficiently than the 5′,8-cyclo- 2′-deoxyadenosine for low O2 concentrations. A high stereoselectivity was observed in the intramolecular addition of the C5′ radical to the C8 of the purine leading, after the creation of the C5′-C8 bond and a subsequent oxidation step, to the predominant formation of the 5′R diastereomer for both purine 5′,8-cyclonucleosides. The reduced formation yield of the 4 tandem lesions in the presence of O2 explains, at least partly, the low efficiency of radiation-induced yields of the purine 5′,8-cyclo-2′-deoxyribonucleosides in cellular DNA, which are about two orders of magnitude lower than the previously reported data obtained from HPLC-MS analysis. The Royal Society of Chemistry 2010.

Radical cascade protocol for the synthesis of (5′S)- and (5′R)-5′,8-cyclo-2′-deoxyguanosine derivatives

The reaction of the appropriately substituted 8-bromo-2′- deoxyguanosine with Bu3SnH/2,2′-azobisisobutyronitrile (AIBN) can be favourably tuned to give the analogous 5′,8-cyclo-2′-deoxyguanosine derivatives in good yields, thus providing easy access to modified nucleosides that constitute an important DNA lesion. A large excess of AIBN is necessary. The creation of the new C5′-C8 bond is a non-chain radical cascade protocol.