Dramatic Effect of Furanose C2 %26apos; Substitution on Structure and Stability: Directing the Folding of the Human Telomeric Quadruplex with a Single Fluorine Atom

作者：Martin Pintado Nerea; Yahyaee Anzahaee Maryam; Deleavey Glen F; Portella Guillem; Orozco Modesto; Damha Masad J^*; Gonzalez Carlos

来源：Journal of the American Chemical Society, 2013, 135(14): 5344-5347.

DOI：10.1021/ja401954t

Human telomeric DNA quadruplexes can adopt different conformations in solution. We have found that arabinose, 2%26apos;F-arabinose, and ribose substitutions stabilize the propeller parallel G-quadruplex form over competing conformers, allowing NMR structural determination of this particularly significant nucleic acid structure. 2%26apos;F-arabinose substitution provides the greatest stabilization as a result of electrostatic (F-CHO4%26apos;) and pseudohydrogen-bond (FH8) stabilizing interactions. In contrast, 2%26apos;F-rG substitution provokes a dramatic destabilization of the quadruplex structure due to unfavorable electrostatic repulsion between the phosphate and the 2%26apos;-F.

• 出版日期2013-4-10