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The Supramolecular Helical Architecture of 8‐Oxoinosine and 8‐Oxoguanosine Derivatives
Author(s) -
Lena Stefano,
Cremonini Mauro A.,
Federiconi Francesco,
Gottarelli Giovanni,
Graziano Carla,
Laghi Luca,
Mariani Paolo,
Masiero Stefano,
Pieraccini Silvia,
Spada Gian Piero
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601126
Subject(s) - mesophase , moiety , supramolecular chemistry , chemistry , lyotropic , derivative (finance) , hydrogen bond , ribose , crystallography , amphiphile , stereochemistry , molecule , copolymer , organic chemistry , crystal structure , phase (matter) , liquid crystalline , enzyme , financial economics , economics , polymer
Abstract The 8‐oxoguanosine derivative 1 and the 8‐oxoinosine derivative 2 b , with appropriate substituents on their ribose moieties, form hexagonal lyotropic mesophases in hydrocarbon solvents. Small‐angle X‐ray scattering analysis of a film of 1 and of the mesophase of 2 b , and NMR and CD spectra of isotropic solutions of 2 b , indicate that in both cases the supramolecular structures adopted are continuous helices formed by a hydrogen‐bond network between the heterocyclic bases. Notably, while derivative 2 b , which bears large substituents on its ribose moiety, undergoes self‐assembly and mesophase formation, oxoinosine 2 a , with only decanoyl groups on its ribose moiety, does not. This may be ascribed to the reduced amphiphilic properties of the latter and the absence of aromatic groups.