Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides

Article abstract of DOI:10.1016/0040-4039(95)00816-U

Reaction of the N-dimethylformamidine (dmf) derivatives of 2'-deoxyguanosine, guanosine, and 2'-deoxyadenosine with iodine and aqueous ammonia gives the corresponding N-cyano nucleosides. This reaction occurs in oligonucleotides under conditions where iodine is retained on the solid support, or in the synthesis column, prior to cleavage with aqueous ammonia. This base modification can be eliminated with lower iodine concentration in the oxidation reagent.