The 2-aminogluconate isomer of Rhizobium sin-1 lipid A can antagonize TNF-α production induced by enteric LPS

摘要: The naturally occurring lipopolysaccharide (LPS) from Rhizobium sin-1, a nitrogen-fixing bacterial species, can prevent the induction of tumor necrosis factor TNF-alpha induced by enteric LPS. proximal saccharide moiety R. sin-1 lipid A exist in two forms, namely as 2-aminogluconolactone or 2-aminogluconate. As it is unknown which these forms responsible for antagonistic properties A, compound 4 was prepared, and its inflammatory were studied. This contains methyl ether at C-5 hydroxyl, prevents lactonization therefore ideally suited to determine whether 2-aminogluconate possesses properties. Compound synthesized highly convergent approach with key disaccharide building block functionalized set orthogonal protecting groups. novel synthetic lacks proinflammatory properties, indicated an absence protein production. was, however, able antagonize production LPS; this indicates that form biological