A novel pyrimidine tetrad contributing to stabilize tetramolecular G-quadruplex structures†
V. Esposito,A. Pepe,R. Filosa,L. Mayol,A. Virgilio,A. Galeone
Organic & Biomolecular Chemistry Pub Date : 02/05/2016 00:00:00 , DOI:10.1039/C5OB02358K
Abstract

G-quadruplex structures formed by oligodeoxyribonucleotides TGGUNH2GGT (AM, UNH2 = 5-amino-2′-deoxyuridine), TGGUBrGGT (BR, UBr = 5-bromo-2′-deoxyuridine) and TGGTGGT (TH) have been investigated through circular dichroism, nuclear magnetic resonance, gel electrophoresis and molecular modeling techniques. Collected data indicate that all 7-mer oligonucleotides form tetramolecular parallel G-quadruplex structures with all residues adopting anti glycosidic bonds. In the case of AM, data suggest the occurrence of a novel UNH2-tetrad characterized by eight hydrogen bonds that stabilizes the G-quadruplex structure more efficiently than UBr- and T-tetrads.

Graphical abstract: A novel pyrimidine tetrad contributing to stabilize tetramolecular G-quadruplex structures