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Synthesis of oxygen-linked 8-phenoxyl-deoxyguanosine nucleoside analogues.

ABSTRACT: Nucleobase adducts, which form in vivo by the nucleophilic attack of nucleobases on exogenous electrophilic species, can impact conformation and biological influences of the adducted nucleoside. Contemporary studies aim to address the occurrence and relevance of O-linked 8-phenoxy-purine adducts; however, preparative techniques for synthesizing these nucleosides were not previously described. Reported herein is a relatively facile synthesis of O-linked 8-dG phenol adducts with a wide variety of electron-donating, electron-withdrawing, and sterically demanding phenols.

SUBMITTER: Dahlmann HA

PROVIDER: S-EPMC3834893 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Synthesis of oxygen-linked 8-phenoxyl-deoxyguanosine nucleoside analogues.

Dahlmann Heidi A HA Sturla Shana J SJ

European journal of organic chemistry 20110601 16

Nucleobase adducts, which form in vivo by the nucleophilic attack of nucleobases on exogenous electrophilic species, can impact conformation and biological influences of the adducted nucleoside. Contemporary studies aim to address the occurrence and relevance of O-linked 8-phenoxy-purine adducts; however, preparative techniques for synthesizing these nucleosides were not previously described. Reported herein is a relatively facile synthesis of O-linked 8-dG phenol adducts with a wi ...[more]

PMID: 24273446

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