Synthetic receptors for peptidic guests

Dowden, James (1996) Synthetic receptors for peptidic guests. University of Southampton, Doctoral Thesis.

Abstract

This thesis describes variations on a simple box shaped design, featuring a carboxylic acid or carboxylate binding site and amide side walls that offer stabilisation and selectivity in the binding of peptidic guests, while rigid aromatic spacers hold open the binding cavity.

Receptor 1 features a simple achiral amide side wall and crown ether functionality that binds to potassium carboxylate salts. The attempted synthesis of 1 by amide bond forming macrocyclisation is described. Carboxylic acids bind to the diamidopyridine functionality of 2 while the chiral side wall offers enantioselectivity. The homochiral synthesis of 2 by amide bond forming macrocyclisation is described. Receptor 2 was shown to be a suitable receptor for peptidic guests. Its selectivity for dipeptides and for L- enantiomers was observed. This clearly demonstrated the role of the amide side wall in selective binding. The design of 3 adjusts the side wall functionality, offering different solubility, selectivity and the possibility of facile derivatisation of the macrocycle in the future. Attempts to synthesise 3 and the side reactions that prevented its formation are described. (Fig 13203)

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