Enhancing Hoogsteen interactions: a pyrrole-containing purine nucleoside that competes with guanosine self-assembly.
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.
Sessler
Jonathan L
JL
Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, 1 University Station A5300, The University of Texas at Austin, Austin, TX 78712-0165, USA. sessler@mail.utexas.edu
Jayawickramarajah
Janarthanan
J
Sherman
Courtney L
CL
Brodbelt
Jennifer S
JS
D001667:Binding, Competitive; D019281:Dimerization; D006151:Guanosine / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D019906:Nuclear Magnetic Resonance, Biomolecular; D011684:Purine Nucleosides / Q000737:chemistry* / Q000378:metabolism; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
D011684:Purine Nucleosides; D011758:Pyrroles; D006151:Guanosine