The Synthesis of Glucosamine-Based Derivatives with Potential as Immunomodulators, Kinase Inhibitors, and Prodrugs

Chapter 1 gives a brief outline of the relevance of carbohydrates in biological systems. Special attention has been given to the roles of glucosamine and N-acetyl glucosamine. Chapter 2 details the synthesis of novel glucosamine-based serine glycolipids, which were tested for their immunomodulatory ability. The experimental conditions investigated are discussed in detail. Chapter 3 describes the synthesis of a glucosamine-based serine building block, and its incorporation into a series of glycopeptides, via SPPS techniques, with potential as a kinase inhibitor. The experimental conditions for the synthesis and purification of these peptides are discussed in detail. Chapter 4 describes an investigation into the introduction of functionalities at the C-6 position of the sugar moiety, with the aim of synthesising an azido-functionalised glucosamine derivative. The experimental details of this investigation are described. Chapter 5 describes the synthesis of a glucosamine-based dopamine derivative, which has potential as a dopamine prodrug. The various approaches taken in this synthesis, and the experimental conditions are discussed in detail. Chapter 6 gives the experimental details and characterisations for the compounds reported throughout this thesis. Chapter 7 contains appendices describing 1H NMR assignation, and also experimental details of attempted experiments. Chapter 8 contains the bibliographic information used as references in this thesis