Efficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole: Generation by a Postsynthetic Substitution Reaction

William L. Neeley, Paul Henderson, John M. Essigmann

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

(Matrix presented) A convertible nucleoside was synthesized and used to prepare the 2′-deoxynucleoside of 5-guanidino-4-nitroimidazole, a putative in vivo product of the reaction of peroxynitrite with guanine. The convertible nucleoside was incorporated into an oligodeoxynucleotide by the phosphoramidite method and converted postsynthetically to yield an oligodeoxynucleotide containing 5-guanidino-4-nitroimidazole at a specific site. The oligodeoxynucleotide was inserted into a viral genome. Melting temperature analysis revealed that duplexes containing 5-guanidino-4-nitroimidazole were greatly destabilized relative to unmodified duplexes.

Original languageEnglish (US)
Pages (from-to)245-248
Number of pages4
JournalOrganic Letters
Volume6
Issue number2
DOIs
StatePublished - Jan 22 2004
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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