Lipid A and Related Compounds. XXXIII.Synthesis and Structure-Activity Relationships of N-Acylated L-Serine or L-Threonine-Containing D-Glucosamine Derivatives as Mimics of Lipid A Disaccharide

Abstract

Four novel N-acylated L-serine or L-threonine-containing non-phosphorylated D-glucosamine derivatives structurally corresponding to the lipid A disaccharide backbone were synthesized. Compounds 2, 3 and 4 exhibited potent mitogenic activity. Among the threonine-linked lipid A analogs (1-3), serine-lipid A analogs (4-6) and homoserine-linked lipid A analogs (7-9), the serine compounds (4, 6) showed the most potent mitogenic activity.