Supramolecular helices via self-assembly of 8-oxoguanosines.
The cooperative effect of solvophobic interactions and hydrogen bonding has been exploited to self-assemble supramolecular helical architectures of 8-oxoguanosines in different environments. This self-assembly into helical structures is completely different from that of the parent guanosines which, in the same experimental conditions, form flat, ribbonlike structures. While optical microscopy and X-ray diffraction suggest a chiral columnar aggregate in the LC phase, NMR and Circular Dichroism reveal the presence of a helical structures in solution. Scanning Tunneling Microscopy made it possible to visualize hexagonally arranged G-quartets on graphite, which are sections of the helices packed with their long axis perpendicular to the basal plane of the substrate. Due to their rectifying electrical properties, such helices are interesting for fabricating (opto)electronic biodevices.
Giorgi
Tatiana
T
Alma Mater Studiorum-Università di Bologna, Dipartimento di Chimica Organica A. Mangini, via San Donato 15, 40127 Bologna, Italy.
Lena
Stefano
S
Mariani
Paolo
P
Cremonini
Mauro A
MA
Masiero
Stefano
S
Pieraccini
Silvia
S
Rabe
Jürgen P
JP
Samorì
Paolo
P
Spada
Gian Piero
GP
Gottarelli
Giovanni
G
D002942:Circular Dichroism; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D009690:Nucleic Acid Conformation; D014961:X-Ray Diffraction
D006151:Guanosine; C046215:8-hydroxyguanosine