Institute for Nanobiomedical Technology and Membrane Biology, Regenerative Medicine Research Center, West China Hospital, West China Medical School, Sichuan University, Chengu, China.
Org Biomol Chem. 2011 Aug 21;9(16):5692-702. doi: 10.1039/c1ob05577a. Epub 2011 Jun 27.
Novel Janus-type nucleoside analogues (1a-d) were synthesized. Their pyrimido[4,5-d]pyrimidine base moiety has one face with a bidentate Watson-Crick donor-acceptor (DA) H-bond array of adenine and the other face with an acceptor-donor (AD) H-bond array of thymine. These nucleosides may self-associate through the self-complementary base pair. Indeed, in the solid state, compound 6d displayed a honeycomb-like supramolecular structure with tetrameric membered cavities formed through the combination of reverse Watson-Crick base pairs and aromatic stacking, in which the solvent molecules were accommodated. The result of temperature-dependent CD studies showed that the free nucleosides can form higher order chiral structures in aqueous solution.
新型的 Janus 型核苷类似物（1a-d）被合成。它们的嘧啶并[4,5-d]嘧啶碱基部分的一个面具有腺嘌呤的双齿 Watson-Crick 供体-受体（DA）氢键排列，另一面具有胸腺嘧啶的受体-供体（AD）氢键排列。这些核苷可能通过自我互补碱基对进行自组装。事实上，在固态下，化合物 6d 通过反 Watson-Crick 碱基对的结合和芳香堆积形成了具有四聚体成员腔的蜂窝状超分子结构，其中容纳了溶剂分子。温度依赖的 CD 研究结果表明，游离核苷在水溶液中可以形成更高阶的手性结构。
