Guanosine Hydrogen‐Bonded Scaffolds: A New Way to Control the Bottom‐Up Realisation of Well‐Defined Nanoarchitectures

Abstract

Over the last two decades, guanosine-related molecules have been of interest in different areas, ranging from structural biology to medicinal chemistry, supramolecular chemistry and nanotechnology. The guanine base is a multiple hydrogen-bonding unit, capable also of binding to cations, and fits very well with contemporary studies in supramolecular chemistry, self-assembly and non-covalent synthesis. This Concepts article, after reviewing on the diversification of self-organised assemblies from guanosine-based low-molecular-weight molecules, will mainly focus on the use of guanine moiety as a potential scaffold for designing functional materials of tailored physical properties.

Biologically derived metal organic frameworks

“…[134][135][136][137] While the above examples highlight the rich coordination modes of Ade leading in the formation of highly porous bio-MOFs, nucleobases such as Gua and their derivatives, are known to form Gquartet, and G-quadruplexes structures which have emerged as powerful tools for developing nanoscale porous materials and devices. [138][139][140][141][142][143][144][145] Verma et al reacted N9-allylguanine and N9-propargylguanine with cupric halides to form three structures ranging from discreet trinuclear motif to a mixed valence coordination polymer (Table 3, entry 16). [146] The first existing example of a crystallographically characterized nucleobase-incorporated metal-organic polyhedron (TMOP-1, Thyincorporated MOP) has also been reported by Zhou et al (Table 3, entry 17).…”

Design, Synthesis and Characterisation of Guanosine‐Based Amphiphiles

“…liminary studies aimed at identifying new tools with the potential to profitably complement the lipophilic congeners recently studied by the research groups of G. P. Spada, [6][7][8][9] J. T. Davis [9][10][11][12] and K. Araki [13][14][15] , among others, further expanding the chemical diversity offered by nucleosides.…”

“…Several supramolecular architectures generated by lipophilic guanosines based on unusual structural motifs, such as G-tetrads stabilised by metal cations or, in the absence of cations, Gribbon structures that in some cases are also organised in sheet-like two dimensional assemblies, have been described in the literature. [6][7][8][9] Herein, the preparation of a set of amphiphilic guanosinebased derivatives by simple synthetic protocols combining different bio-inspired building blocks is described. Their structural and biological properties are investigated in preAbstract: A small library of sugarmodified guanosine derivatives has been prepared, starting from a common intermediate, fully protected on the nucleobase.…”

Stacked and continuous helical self-assemblies of guanosine monophosphates detected by vibrational circular dichroism

“…1), which is characteristic of stacked quartets with "head-to-tail"-type stacking. Crystallographic studies, NMR, and small-angle neutron scattering revealed that K + facilitated an octamer structure, (G4) 2 , with K + cations positioned out of the G4 plane and coordinating with the O atoms in the other G4 (see [26,27]). Figure 2 demonstrates the changes observed in the spectra obtained from aqueous solutions of GMP, GDP, and GTP after the addition of Na + and K + .…”