Towards a second generation of macrotricyclic receptors for carbohydrate recognition

Chapter One provides a brief introduction to Supramolecular Chemistry. The interactions involved in supramolecular phenomena as well as the principles for receptor design are outlined. The factors concerning carbohydrate recognition in the natural world are briefly described. Special attention is paid to the development of synthetic receptors for carbohydrates operating in aqueous or organic media. The aims of the project are introduced. Chapter Two deals with the synthesis of two novel pyridyl derived macrotricyclic receptors. The different procedures involved in the preparation of the corresponding pyridyl derived spacer group are also discussed. Chapter Three describes the study of the binding properties of the two novel pyridyl derived macrotricyclic receptors. 1H-NMR and fluorescence titrations are examined. Extraction experiments of different monosaccharides from aqueous into organic media are also discussed. Chapter Four presents the synthesis of a tri-differentially N-protected biaryl unit necessary for the development of a new family of receptors with variations in 'one corner'. Preliminary studies towards the synthesis of macrobicyclic receptors are discussed. Chapter Five is a detailed account of the experimental procedures for the syntheses of the compounds reported in this thesis. (author)