title: N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.
abstract: 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-aminopurine ribonucleoside analogs and their phosphoramidites, 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.
authors.affiliation: Department of Chemistry, University of California, Davis, California 95616, USA.
authors.forename: Hayden
authors.initials: H
authors.lastname: Peacock
authors.forename: Olena
authors.initials: O
authors.lastname: Maydanovych
authors.forename: Peter A
authors.initials: PA
authors.lastname: Beal
mesh_terms: D015075:2-Aminopurine / Q000737:chemistry*; D000241:Adenosine / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D020029:Base Pairing; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D012330:RNA, Double-Stranded / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D009943:Organophosphorus Compounds; D012330:RNA, Double-Stranded; C434331:phosphoramidite; D015075:2-Aminopurine; D003300:Copper; D000241:Adenosine; D009584:Nitrogen