Chemical synthesis of phosphorylated tetraacyl disaccharide corresponding to a biosynthetic precursor of lipid A

✍ Scribed by M. Imoto; H. Yoshimura; M. Yamamoto; T. Shimamoto; S. Kusumoto; T. Shiba

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 296 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81258-2

✦ Synopsis

A total synthesis of 2,2'-N; 3,3'-O-tetraquis[(R)-3-hydroxytetradecanoyl]-~(l-6)-Dglucosamine disaccharide 1,4'-diphosphate is described. This is the first confirmation of the fundamental structure of lipid A since the synthetic compound exhibited most of the characteristic biological activities of natural endotoxin. The cell-surface lipopolysaccharide (LPS) of Gram-negative bacteria is designated as endotoxin which exhibits many characteristic biological activities. Most of them have been attributed to the lipophilic portion of the molecule called lipid A which can be liberated from LPS by mild acid hydrolysis. The basic chemical structure of lipid A was postulated to be a polyacylated B(l-6)-D-glucosamine disaccharide 1,4'-diphosphate. 1) The positions of acyl