The supramolecular helical architecture of 8-oxoinosine and 8-oxoguanosine derivatives.
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.
Lena
Stefano
S
Alma Mater Studiorum-Università di Bologna, Dipartimento di Chimica Organica "A. Mangini", Via San Giacomo 11, 40126 Bologna, Italy.
Cremonini
Mauro A
MA
Federiconi
Francesco
F
Gottarelli
Giovanni
G
Graziano
Carla
C
Laghi
Luca
L
Mariani
Paolo
P
Masiero
Stefano
S
Pieraccini
Silvia
S
Spada
Gian Piero
GP
D000473:Alkanes / Q000737:chemistry; D002942:Circular Dichroism; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry; D006860:Hydrogen Bonding; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry; D050866:Liquid Crystals / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012266:Ribose / Q000737:chemistry; D012542:Scattering, Radiation; D012997:Solvents / Q000737:chemistry*; D014961:X-Ray Diffraction
C521668:8-oxoinosine; D000473:Alkanes; D006571:Heterocyclic Compounds; D006838:Hydrocarbons; D012997:Solvents; D006151:Guanosine; C046215:8-hydroxyguanosine; D007288:Inosine; D012266:Ribose; C012867:decane