A method for thegeneration of dG FaPy lesions in synthetic oligonucleotides has beendeveloped. The procedure includes preparation of the syntheticoligonucleotide precursor containing 5-nitropyrimidine moiety. Afterdeprotection and purification of the oligonucleotide by standardprocedures, the nitro group is reduced by catalytic hydrogenationfollowed by formylation of the newly formed amino group with formylimidazole in water-organic solution. The method allows a large-scalepreparation of oligonucleotides containing an equilibrium mixture ofalpha and beta FaPy anomers. The anomeric oligonucleotidesinterconvert very slowly in neutral conditions and can bechromatographically separated. Spectroscopic proterties,  meltingbehaviour and interconversion of the FaPy containing oligonucleotidesare discussed.

Post-synthetic
generation of FaPy lesions in oligonucleotides

240th National Meeting (2010)

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Post-synthetic generation of FaPy lesions in oligonucleotides