92949-59-2Relevant academic research and scientific papers
CHEMICAL SYNTHESIS OF PHOSPHORYLATED TETRAACYL DISACCHARIDE CORRESPONDING TO A BIOSYNTHETIC PRECURSOR OF LIPID A
Imoto, M.,Yoshimura, H.,Yamamoto, M.,Shimamoto, T.,Kusumoto, S.,Shiba, T.
, p. 2667 - 2670 (1984)
A total synthesis of 2,2'-N; 3,3'-O-tetraquis-β(1-6)-D-glucosamine 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.
Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure
Imoto, Masahiro,Yoshimura, Hiroyuki,Yamamoto, Michiharu,Shimamoto, Tetsuo,Kusumoto, Shoichi,Shiba, Tetsuo
, p. 2197 - 2204 (2007/10/02)
2,2'-N:3,3'-O-Tetrakis-β(1-6)-D-glucosamine disaccharide 1,4'-bis(phosphate) and its dephospho derivatives were synthesized.The bisphosphate prepared was shown to be identical with a natural biosynthetic precursor of lipid A which corresponds to the lipophilic part of lipopolysaccharide (LPS) in bacterial cell wall.The synthetic bis- and monophosphates exhibited many of typical endotoxic activities of LPS.Consequently, this work established the chemical structure of the biosynthetic precursor of lipid A and elucidated the fundamental structure required for the expression of these activities.
