Stereoselective synthesis of glycerol-based lipids

In Nature, lipid (fat) molecules exist as mixtures of several tens to hundreds of different, but closely related molecules. Some members of these large collectives of molecules might have a unique function. For example, some specific triacylglycerols from breast milk grant the adsorption of calcium from the intestine of children. Calcium is essential for healthy grow. Another example is fish oil. Here again some specific triacylglycerols ’scrape the plaque’ from the veins and as a result the ’bad LDL cholesterol’ decreases. This is beneficial for cardiac health.

In order to study how these specific lipids work, they have to be isolated from their natural source, what can be tedious and time consuming. Alternatively, these molecules can be chemically synthesized. However, this requires efficient procedures, which are very often lacking.

This issue is addressed in this thesis, where novel and efficient methods for the preparation of different (bioactive) lipids are presented. The presented research does not finish only with the preparation of the lipids, also their properties are studied. Some of the lipids found their way to FrieslandCampina, where they facilitate the analysis of milk fat. Other lipids were used for studies of the activity of antifungal drugs or facilitated other scientists to study metabolic pathways in Archaea.

Dissertation: http://irs.ub.rug.nl/ppn/391579029