Nucleoside- and Nucleobase-Substituted Oligopyrrolic Macrocycles


Jonathan L. Sessler Department of Chemistry and Biochemistry, University of Texas at Austin

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This chapter summarizes the design and synthesis of conjugates resulting from the combination of nucleic acid base derivatives, particularly nucleosides and nucleotides, with oligopyrrole macrocycles. In addition to detailing the methods of preparation and fundamental chemical properties, the vision behind such projects and the various applications targeted for use by these conjugates are also described. These systems combine into one chemical entity two of the more important biological building blocks found in Nature, namely, nucleic acid bases (nucleobases) and porphyrins, and this leads to new constructs with rather unique chemical features as well as novel molecular recognition properties. Although the focus of the present chapter will be on systems containing natural nucleobase components, it is important to appreciate that the porphyrin portion of these constructs can include a range of synthetic oligopyrrole macrocycles that have no biological equivalent. This gives rise to products with unexpected supramolecular properties, including those associated with anion recognition.