Tetrahedron Letters p. 7455 - 7458 (1995)
Update date:2022-08-18
Topics:
Fukase, Koichi
Liu, Wen-Chi
Suda, Yasuo
Oikawa, Masato
Wada, Akira
Mori, Saeko
Ulmer, Arthur J.
Rietschel, Ernst Th.
Kusumoto, Shoichi
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.
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