Synthesis of oligosaccharides for structural, conformational and molecular recognition investigations

Sammanfattning: Carbohydrates are involved cell-cell interaction. Synthesis of small and medium sized oligosaccharides is important to gain more understanding about the their physical properties that are crucial for their action in molecular recognition events. The first paper describes the synthesis, structural and conformational analysis of four different trisaccharides. The second paper describes a stereospecific synthesis of methyl a-(4-2H)-cellobioside, applying a regioselective oxidation stereospecific reduction sequence. In the third paper investigation of 1,3-dibromo-5,5-dimethylhydantoin in regioselective oxidation of stannylene acetals of different monosaccharide diols is described. The fourth study describes the synthesis of three different trisaccharides related to Escherichia coli O35 and Salmonella arizona O62, where the selective oxidation of a hydroxymethyl group using TEMPO is the key step. The last work summarize the synthesis of a model hexasaccharide from the core region of a Haemonchus contortus glycoprotein. The key steps in this synthesis are regioselective glucosidation to form a trisaccharide core followed by trifucosylation and conversion of a b-glucoside to the corresponding b-mannoside.