Sessler, J. L.; Jayawickramarajah, J.; Sherman, C. L.; Brodbelt, J. S. Enhancing Hoogsteen Interactions: A Pyrrole-Containing Purine Nucleoside That Competes with Guanosine Self-Assembly. Journal of the American Chemical Society 2004, 126, 11460-11461.
Abstract
A pyrrole-appended purine nucleoside 1 is described that can form an “extended” three-point Hoogsteen-type interaction due to the stabilization of the donor−acceptor−acceptor (DAA) motif. Nucleoside 1 is shown to bind guanosine 10 (a classic ADD motif) to form ensemble I. This interaction competes effectively with guanosine self-assembly and, as such, is capable of disrupting guanosine quadruplex formation.
