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 e...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2004-09, Vol.126 (37), p.11460-11461
Main Authors: Sessler, Jonathan L, Jayawickramarajah, Janarthanan, Sherman, Courtney L, Brodbelt, Jennifer S
Format: Article
Language:English
Subjects:
Binding, Competitive
Biological and medical sciences
Dimerization
Fundamental and applied biological sciences. Psychology
Guanosine - chemistry
Guanosine - metabolism
Hydrogen Bonding
Interactions. Associations
Intermolecular phenomena
Molecular biophysics
Nuclear Magnetic Resonance, Biomolecular
Purine Nucleosides - chemistry
Purine Nucleosides - metabolism
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - metabolism
Spectrometry, Mass, Electrospray Ionization
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja046773v