ol036188j_si_001.pdf (625.51 kB)
Download fileEfficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole: Generation by a Postsynthetic Substitution Reaction
journal contribution
posted on 22.01.2004, 00:00 authored by William L. Neeley, Paul T. Henderson, John M. EssigmannA 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.