Guanosine self-assembly

A.L. Webber, S. Masiero, S. Pieraccini,J.C. Burley, A.S. Tatton, D. luga, T.N. Pham, G. Spada, S.P. Brown, Identifying guanosine self assembly at natural isotopic abundance by high-resolution H and C solid-state NMR spectroscopy, J. Am. Chem. Soc. 133 (2011) 19777-19795. 

Several natural and synthetic helical macromolecules such as DNA, polypeptides, and polyisocyanates form, in the appropriate solvent, cholesteric meso-phases. Also self-assembled supramolecular systems formed by guanosine derivatives 2 and 3 (G-wires), which are essentially four-stranded helices (Figure 7.8), behave in a similar way.35... 

Figure 5.8 Self-assembled dimer of 5.25 with Na+ binding by a guanosine tetramer motif (G-quartet) and Cl- binding by amide functionalities. Remaining space if filled by water molecules. (Reproduced with permission from [22] 2003 American Chemical Society).

Lyotropic (in solvent) cholesteric mesophases have been observed for self-assembled guanosine derivatives. In water, the compounds shown in Fig. 10 generate left-handed columnar aggregates [91]. When the concentration is sufficiently high, cholesteric phases are formed which also have a left-handed twist, as determined by CD spectroscopy. The same tetrameric motif is present in the lyomesophases formed by more lipophilic guanosine deriva-... 

Davis JT, Spada GP (2007) Supramolecular architectures generated by self-assembly of guanosine derivatives. Chem Soc Rev 36 296-313... 

Guanine and guanosine are, of course, commercially available and can be derivatized in numerous ways. Along these lines, Sessler has used [32] a palladium-catalyzed Stille coupling to connect a porphyrin system to 8-bromoguanosine for use in a self-assembling, photosynthetic model system... 

Supramolecular architectures generated by self-assembly of guanosine derivatives 07CSR296. 

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