Studies in Host-Guest Chemistry

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Abstract

Previous work in our group has been directed towards the synthesis of crown-ethers for use in the selective complexation of metal ions and as chiral ligands for use in asymmetric catalysis. The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine-based macrocycles possessing multiple donor sites where chirality was readily introduced from simple amino acids.The nucleophilic ring opening of aziridines 181, 193 or 194, allowed the highly selective synthesis of thioether-based spacers and macrocycles. Extension of this basic approach to the synthesis of seleno-crown ethers was also investigated. The use of chiral-pool starting materials derived from D- or L-alanine, provided access to optically pure macrocycles.The use of the Sharpless-Huisgen “click” reactions allowed the attachment of a carbohydrate residue directly to a macrocycle via a triazole unit. We hope to attach a macrocycle, carbohydrate residue and azo dye together, to be able to examine further diseases such as Alzheimer’s. We have so far succeeded in attaching a macrocycle and sugar to a central scaffold by performing a one-pot double “click” reaction. The distance between the points of attachment of the chromophore to the macrocycle metal binding site is probably, in this first generation sensor, too great to enable a metal-macrocycle binding event to be reported.

Keyword(s)

aziridine; azo dye; click; crown; ionophore; ligand; macrocycle; macrocyclisation

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