title: Enhancing Hoogsteen interactions: a pyrrole-containing purine nucleoside that competes with guanosine self-assembly.
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.
authors.affiliation: 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
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Sessler
authors.forename: Janarthanan
authors.initials: J
authors.lastname: Jayawickramarajah
authors.forename: Courtney L
authors.initials: CL
authors.lastname: Sherman
authors.forename: Jennifer S
authors.initials: JS
authors.lastname: Brodbelt
mesh_terms: 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
chemical_list: D011684:Purine Nucleosides; D011758:Pyrroles; D006151:Guanosine