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G(boolean AND)C quartet - A DNA-inspired Janus-GC heterocycle: Synthesis, structural analysis, and self-organization

TitleG(boolean AND)C quartet - A DNA-inspired Janus-GC heterocycle: Synthesis, structural analysis, and self-organization
Publication TypeJournal Article
Year of Publication2008
AuthorsAsadi, A, Patrick, BO, Perrin, DM
JournalJournal of the American Chemical Society
Volume130
Pagination12860-+
Date PublishedOct
Type of ArticleArticle
ISBN Number0002-7863
KeywordsBASE, CHEMISTRY, COMPLEXES, DERIVATIVES, FOLIC-ACID SALTS, HELICAL ROSETTE NANOTUBES, HYDROGEN-BONDED NETWORKS, MOLECULAR TECTONICS, RECOGNITION, solid-state structures
Abstract

In this communication we disclose the synthesis and characterization of a DNA-inspired self-complementary heterocycle that contains AAD-DAA H-bond acceptor/donor patterns. Whereas in the past such AAD-DAA self-complementarity has given rise to trimeric and hexameric rosettes, we now demonstrate that the same H-bonding scheme, when properly arrayed, can be used to program a tetrameric rosette, which unlike a G-quartet requires no metal binding or peripheral components for p reorganization. Of note, we exploit both 2D-NOESY and DOSY H-1 NMR to substantiate the tetrameric stoichiometry in this noncovalent rosette comprising 12 H-bonds.

URL<Go to ISI>://000259553700012