N²-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA

"Chemical equation presented" Nucleoside analogs that project substituents Into the minor groove when incorporated into duplex RNA perturb the binding of proteins and can affect base pairing specificity. The synthesis of 2-amlnopurine ribonucleoside analogs and their phosphoramldites, their incorporation into duplex RNA, their postsynthetic modification via Cu-catalyzed azide-alkyne cycloaddition (CuAAC), and their effect on duplex stability and base pairing specificity are described.