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Synthesis of 8‐Phenoxy‐2′‐deoxyguanosine Nucleoside Analogues
Author(s) -
Dahlmann Heidi A.,
Sturla Shana J.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100013
Subject(s) - nucleobase , chemistry , electrophile , steric effects , deoxyguanosine , nucleoside , adduct , nucleophile , stereochemistry , combinatorial chemistry , dna , organic chemistry , biochemistry , catalysis
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.