N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.
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.
Peacock
Hayden
H
Department of Chemistry, University of California, Davis, California 95616, USA.
Maydanovych
Olena
O
Beal
Peter A
PA
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*
D000480:Alkynes; D001386:Azides; D009943:Organophosphorus Compounds; D012330:RNA, Double-Stranded; C434331:phosphoramidite; D015075:2-Aminopurine; D003300:Copper; D000241:Adenosine; D009584:Nitrogen