Enhancing Hoogsteen interactions: a pyrrole-containing purine nucleoside that competes with guanosine self-assembly

Jonathan L Sessler; Janarthanan Jayawickramarajah; Courtney L Sherman; Jennifer S Brodbelt

doi:10.1021/ja046773v

Enhancing Hoogsteen interactions: a pyrrole-containing purine nucleoside that competes with guanosine self-assembly

J Am Chem Soc. 2004 Sep 22;126(37):11460-1. doi: 10.1021/ja046773v.

Authors

Jonathan L Sessler¹, Janarthanan Jayawickramarajah, Courtney L Sherman, Jennifer S Brodbelt

Affiliation

¹ 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

PMID: 15366891
DOI: 10.1021/ja046773v

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding, Competitive
Dimerization
Guanosine / chemistry*
Guanosine / metabolism
Hydrogen Bonding
Nuclear Magnetic Resonance, Biomolecular
Purine Nucleosides / chemistry*
Purine Nucleosides / metabolism
Pyrroles / chemical synthesis
Pyrroles / chemistry*
Pyrroles / metabolism
Spectrometry, Mass, Electrospray Ionization

Substances

Purine Nucleosides
Pyrroles
Guanosine