The oligosaccharides (OS) in milk are known to play essential roles in the development of the infant. However, the carbohydrate composition of milk from different animal sources as well as human milk varies. Formulated infant milkpowder made from cow milk lacks certain bioactive carbohydrate structures and shows limited amounts of N-acetylneuraminic acid and fucose, compared to human milk. Our strategy to discover the difference of bioactive carbohydrate structures in milk and the potential for the development of novel functional dairy products is based on the analysis of glycosylation profiles of free and protein bound OS with a unique chromatography-based methodology. This approach is currently also adopted for a broader range of foodstuff, which shows carbohydrate related biological functions. Additionally, the level of nutritional components (e.g. lipids) has been found to influence many biological events. The effect of the nutritional level on glycan structures is also of great interest and to monitor the structural changes, and to reveal the underlying biochemical mechanisms is another target of our research.