The viral-surface envelope glycoproteins of HIV are abundantly decorated with complex and high mannose type N-glycans (> 20 glycosylation sites). Synthesis of a large number of closely related structural determinants of high mannose antennae was carried out by means of the combination of conventional and combinatorial carbohydrate chemistry. The chitobiose part of the core structure was replaced by a simple octyl aglycone. The pseudo tetra-(2) and penta-(3)-saccharides were prepared by standard carbohydrate chemistry. The p-mannosidic linkage was created by the oxidation-reduction technique. Random mannosylation of acceptors 2 and 3 resulted in a mixture of predominantly pseudo penta-and hexasaccharides, respectively. After removal of the protecting groups, the interaction of the synthesized mixture of oligosaccharides and gp120 binding proteins will be investigated.
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