Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues |
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Authors: | St Amant André H Bean Leslie A Guthrie J Peter Hudson Robert H E |
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Affiliation: | Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7. |
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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. |
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