Synthesis of 8-Phenoxy-2'-deoxyguanosine Nucleoside Analogues

Nucleobase adducts, which form in vivo by nucleophilic attack of nucleobases on electrophilic chemical species, can impact on the conformation and biological influences of the adducted nucleoside. Contemporary studies aim to address the occurrence and relevance of 8-phenoxypurine adducts. However, preparative techniques for synthesizing these nucleosides have not previously been described. Reported herein is a relatively facile synthesis of 8-dG phenol adducts using a wide variety of electron-donating, electron-withdrawing, and sterically demanding phenols.