Synthesis of the sialic acid 9-C derivative with an amino group replacing the OH-group.

Sammanfattning: Almost everyone is aware of the big problem with increasing antibiotic resistance among bacteria and the importance and need of developing new antibiotics. This bachelor thesis is a part of one such project with the aim to find new possible antibiotics. A promising candidate is a derivative of the sialic acids. The sialic acids are important molecules in the human body where it from the cell membrane is responsible for a lot of the communication between cells. One of its many messages is between the human cells and the immune system where it signalizing that they are human and not harmful. This is something many bacteria has choose to take advantage of by developing a method to absorb this molecule and place it at their own cell membrane, and in that way hinder the immune system from recognize them as bacteria. Thus, this process is an interesting target for new antibiotics and by inhibiting the involved transport protein at the bacteria we can stop this process. Therefore this project has been part of a larger study where the aim is to find and synthesize a sialic acid derivative that can bind more strongly to the involved protein than the natural ligand. Previous studies have resulted in one promising candidate, the sialic acid derivative where the OH-group at carbon 9 has been replaced by an amino group. With the intention to study this molecule more my focus has been to synthesize this molecule again. The synthesis has been quite problematic and has not resulted in the intended amine. However, it has led to some improvements of the synthetic pathway as well as new insights in the reactions, for example that protecting groups might be needed.