Web Release Date: April 13,
Confinement of Nucleic Acid Bases and Related Compounds Using Tetra-p-sulfonatocalix[4]arene
and
School of Chemistry, Monash University, Melbourne, Victoria 3800, Australia, and School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, Perth, WA 6009, Australia
Received December 20, 2005
Revised February 16, 2006
Abstract:
Supramolecular complexes of tetra-p-sulfonatocalix[4]arene and guanine, cytosine, benzimidazole, and 2-hydroxybenzimidazole have been isolated in the solid state, and their structures have been elucidated using single-crystal X-ray diffraction data, as have 2-hydroxybenzimidazole complexes and complexes with large cations tetraphenylphosphonium (Ph4P+) and triethylbenzylammonium (Et3BzN+). These large cations disrupt the usual bilayer arrangement of the sulfonated calixarenes, as can benzimadole itself, and a combination of guanine and cytosine, in the absence of the large cations. Some of the structures show a "molecular capsule" type arrangement with two calixarenes arranged with their cavities directed toward each other, effectively shrouding two nucleic acid bases.
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