Supramolecular architectures generated by self-assembly of guanosine derivatives

被引:576
作者
Davis, Jeffery T. [1 ]
Spada, Gian Piero
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
[2] Univ Bologna, Alma Mater Studiorum, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy
关键词
D O I
10.1039/b600282j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nature's use of a simple genetic code to enable life's complex functions is an inspiration for supramolecular chemistry. DNA nucleobases carry the key information utilizing a variety of cooperative and non-covalent interactions such as hydrophobic, van der Waals, pi-pi stacking, ion-dipole and hydrogen bonding. This tutorial review describes some recent advances in the form and function provided by self-assembly of guanine (G) based systems. We attempt to make connections between the structures of the assemblies and their properties. The review begins with a brief historical context of G self-assembly in water and then describes studies on lipophilic guanosine analogs in organic solvents. The article also focuses on examples of how G analogs have been used as building blocks for functional applications in supramolecular chemistry, material science and nanotechnology.
引用
收藏
页码:296 / 313
页数:18
相关论文
共 56 条
[31]   Field effect transistor based on a modified DNA base [J].
Maruccio, G ;
Visconti, P ;
Arima, V ;
D'Amico, S ;
Blasco, A ;
D'Amone, E ;
Cingolani, R ;
Rinaldi, R ;
Masiero, S ;
Giorgi, T ;
Gottarelli, G .
NANO LETTERS, 2003, 3 (04) :479-483
[32]  
NEOGI A, 2004, ELECTRON LETT, V40, P25
[33]   Guanine quartet networks stabilized by cooperative hydrogen bonds [J].
Otero, R ;
Schöck, M ;
Molina, LM ;
Lægsgaard, E ;
Stensgaard, I ;
Hammer, B ;
Besenbacher, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2270-2275
[34]   Selection and amplification of hosts from dynamic combinatorial libraries of macrocyclic disulfides [J].
Otto, S ;
Furlan, RLE ;
Sanders, JKM .
SCIENCE, 2002, 297 (5581) :590-593
[35]  
Pieraccini S, 2001, CHIRALITY, V13, P7, DOI 10.1002/1520-636X(2001)13:1<7::AID-CHIR3>3.0.CO
[36]  
2-M
[37]   Reversible interconversion between a supramolecular polymer and a discrete octameric species from a guanosine derivative by dynamic cation binding and release [J].
Pieraccini, Silvia ;
Masiero, Stefano ;
Pandoli, Omar ;
Samori, Paolo ;
Spada, Gian Piero .
ORGANIC LETTERS, 2006, 8 (14) :3125-3128
[38]   ALKALI-METAL ION SPECIFICITY IN SOLUTION ORDERING OF A NUCLEOTIDE, 5'-GUANOSINE MONOPHOSPHATE [J].
PINNAVAIA, TJ ;
MARSHALL, CL ;
METTLER, CM ;
FISK, CI ;
MILES, HT ;
BECKER, ED .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3625-3627
[39]   Hybrid molecular electronic devices based on modified deoxyguanosines [J].
Rinaldi, R ;
Maruccio, G ;
Biasco, A ;
Arima, V ;
Cingolani, R ;
Giorgi, T ;
Masiero, S ;
Spada, GP ;
Gottarelli, G .
NANOTECHNOLOGY, 2002, 13 (03) :398-403
[40]   Photodetectors fabricated from a self-assembly of a deoxyguanosine derivative [J].
Rinaldi, R ;
Branca, E ;
Cingolani, R ;
Masiero, S ;
Spada, GP ;
Gottarelli, G .
APPLIED PHYSICS LETTERS, 2001, 78 (22) :3541-3543