Site-Selective Oxidation & Further Modification of Unprotected Carbohydrates

Carbohydrates are the most abundant molecules in nature and play a crucial role in living organisms. However, unravelling the structure and/or the biological function of carbohydrates is a formidable challenge. They are structurally very complex and contain a large number of reactive groups. In order to study carbohydrates, chemical syntheses and chemical modifications of carbohydrates are needed.In our research group, we study a reaction that can transform a single alcohol functionality of a carbohydrate to a ketone group. This transformation can also be described as the selective oxidation of carbohydrates. This is a valuable transformation because the ketone resulting from oxidation allows further modifications in the presence of alchols. During my PhD I have applied the selective oxidation to convert a sugar molecule into new building blocks. In addition, the reaction was applied to aminoglycoside antibiotics, which resulted into seven new antibiotic derivatives. Finally, the selective oxidation reaction was used in a sequence of chemical reactions to prepare the natural product Dissectol A