title: Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues.
abstract: The synthesis of nucleoside analogues incorporating 4-(5-pyrimidinyl)-1,2,3-triazole aglycons as expanded purine nucleobase mimics were accessed using the copper-catalyzed azide-alkyne Huisgen cycloaddition between a ribosyl azide and 5-alkynylpyrimidines. Depending on the nature of the alkyne employed, other nucleoside analogues that possess fluorescence or potential metal-binding properties were prepared. Computational studies were undertaken on the purine analogues and indicate that the heterocycles of the unfused nucleobase prefer a coplanar arrangement and the anti-glycosidic conformer is favoured in most instances.
authors: Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
authors: André H
authors: AH
authors: St Amant
authors: Leslie A
authors: LA
authors: Bean
authors: J Peter
authors: JP
authors: Guthrie
authors: Robert H E
authors: RH
authors: Hudson
mesh_terms: D002384:Catalysis; D057930:Click Chemistry; D003198:Computer Simulation; D003300:Copper / Q000737:chemistry* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000737:chemistry* / Q000378:metabolism; D012263:Ribonucleosides / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D006571:Heterocyclic Compounds; D011684:Purine Nucleosides; D012263:Ribonucleosides; D003300:Copper