Synthesis of an analog of biosynthetic precursor la of lipid A by an improved method: A novel antagonist containing four (S)-3-hydroxy fatty acids

Article abstract of DOI:10.1016/0040-4039(95)01433-0

Synthesis of an analog of a biosynthetic precursor of lipid A containing four (S)-3-hydroxytetradecanoic acids was effected via an improved synthetic route to investigate the relationship between the bioactivity and the chirality of the 3-hydroxy fatty acid residues in lipid A. The S-analog inhibited endotoxin-induced interleukin-6 (IL-6) production from human peripheral whole blood cells more strongly than the natural-type biosynthetic precursor with (R)-hydroxy acids, a known antagonist of LPS-induced cytokine release in human peripheral blood mononuclear cells.