Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Org Biomol Chem. 2012 Aug 28;10(32):6521-5. doi: 10.1039/c2ob25678a. Epub 2012 Jul 3.
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.
核苷类似物的合成，其中包含 4-(5-嘧啶基)-1,2,3-三唑糖苷作为扩展的嘌呤核苷类似物，是通过铜催化的叠氮化物-炔烃 Huisgen 环加成反应，在核糖叠氮化物和 5-炔基嘧啶之间进行的。根据所使用的炔烃的性质，还制备了具有荧光或潜在金属结合性质的其他核苷类似物。对嘌呤类似物进行了计算研究，表明未融合的核苷碱基的杂环更喜欢共面排列，并且在大多数情况下，反糖苷构象是有利的。
