Search

Three different β-linked divalent mannosides, along with their corresponding monovalent counterparts, have been designed and chemically synthesized by coupling the corresponding propargyl (propargyl alcohol in the case of the monovalent compounds) and 2-azidoethyl glycosides by using an efficient click chemistry protocol. Crich's β-mannosylation methodology was applied to the construction of the β-mannosidic linkages. All the glycosylation reactions gave moderate-to-good yields with high selectivities. A competitive inhibition enzyme-linked immunosorbent assay (ELISA) was performed to determine the inhibition, by the synthesized mannosides, of specific human IgG binding to low-molecular-weight Candida albicans mannan; moderate inhibition capacity was observed for some of the compounds.

Immunostimulatory properties of synthetic structures mimicking the β-(1→2)-linked mannans ofCandida albicanswere evaluatedin vitro. Contrary to earlier observations, tumor necrosis factor (TNF) production was not detected after stimulation with mannotetraose in mouse macrophages. Divalent disaccharide 1,4-bis(α-d-mannopyranosyloxy)butane induced TNF and some molecules induced low levels of gamma interferon (IFN-γ) in human peripheral blood mononuclear cells (PBMC).