Walking a Supramolecular Tightrope: A Self-Assembled Dodecamer from an 8-Aryl-2′-deoxyguanosine Derivative

• Published in: Journal of the American Chemical Society Vol. 131; no. 30; pp. 10403 - 10405
• Main Authors: Rivera-Sánchez, María del C, Andújar-de-Sanctis, Ivonne, García-Arriaga, Marilyn, Gubala, Vladimir, Hobley, Gerard, Rivera, José M
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 05.08.2009
• Subjects: Communication; Deoxyguanosine - analogs & derivatives; Deoxyguanosine - chemistry; Hydrophobic and Hydrophilic Interactions; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Conformation; Polymers - chemical synthesis; Polymers - chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja9040384

Controlling the properties of self-assembled supramolecules via intrinsic parameters (i.e., structural information in the subunits) enables the reliable construction of assemblies of well-defined size and composition. Here we show that an optimum balance between repulsive (e.g., steric) and attractive (e.g., π−π, dipole−dipole) noncovalent interactions between subunits of a lipophilic 8-(3-pyridyl)-2′-deoxyguanosine derivative enables the high fidelity formation of a stable and discrete self-assembled dodecamer. In contrast, the isosteric 8-phenyl-2′-deoxyguanosine derivative assembles into an octamer because it cannot engage in additional dipole−dipole interactions. Adding dodecamers to a supramolecular construction toolbox, already containing octamers and hexadecamers made from other 8-aryl-2′-deoxyguanosine derivatives, should enable the preparation of a wide variety of self-assembled nanostructures where the size and the number of functional elements can be precisely fine-tuned for specific applications.