The development of enantioselective receptors for amino acid derivatives

Abstract

This thesis is concerned with the synthesis and investigation of the properties of novel bicyclic receptors for amino acid derivatives. Chapter two describes the synthesis of a previously reported macrocycle, 1, which had the potential to enhance the rate of intermolecular Diels-Alder cyclisations on substrates such as 26. Chapter three describes the synthesis of substrates based on the structure of 26 and the experiments carried out to determine whether or not macrocycle 1 could enhance the reaction rate. It was found that macrocycle 1 did not have an effect on the rates of intramolecular Diels-Alder cyclisations of these substrates. Chapter four describes the synthesis of two novel macrobicylces 59 and 60 which feature novel aromatic spacer units in the macrocycle rim for the purpose of enhancing the binding selectivity over that of macrocycle 1. Attention is given to the characterisation of the two macrocycles and the investigation of the binding properties of macrocycle 59 with several amino acid guests. The fifth chapter goes on to describe the attempted synthesis of a further two novel macrobicycles, 72 and 77 which incorporate a bis carboxylate binding site for the complexation of glutamate and aspartate derivatives (Fig 13332.)

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