Methanol soluble and stable guanosine octamers were successfully achieved via H-bond self-assembly. Through structural conformational design, we developed a new class of guanosine derivatives with modification on guanine (8-aryl) and ribose (20 ,30 -isopropylidene). This unique design led to the formation of the first discrete G8-octamer with its structure characterized by single crystal X-ray diffraction, MS and NMR spectroscopy. The G8-octamer showed unique cation recognition properties, including the formation of a stable Rb+ templated G-quadruplex. Based on this observation, further modification on the 8-aryl moiety was performed to incorporate a cross-layer H-bond or covalent linkage. Similar G-octamers were obtained in both cases with structures confirmed by single crystal X-ray diffraction. Furthermore, the covalently linked G-quadruplex exhibited excellent stability even in MeOH and DMSO, suggesting a promising future for this new H-bond self-assembly system in biological and material applications.
Digital Commons Citation
He, Ying; Zhang, Yanbin; Wojtas, Luksaz; Akhmedov, Novruz G.; Thai, David; Wang, Heng; Li, Xiaopeng; Guo, Hao; and Shi, Xiaodong, "Construction of a Cross-layer Linked G-octamer via Conformational Control: A Stable G-quadruplex in H-bond Competitive Solvents" (2019). Faculty & Staff Scholarship. 2139.
He, Y., Zhang, Y., Wojtas, L., Akhmedov, N. G., Thai, D., Wang, H., Li, X., Guo, H., & Shi, X. (2019). Construction of a cross-layer linked G-octamer via conformational control: a stable G-quadruplex in H-bond competitive solvents. Chemical Science, 10(15), 4192–4199. https://doi.org/10.1039/c9sc00190e