Absolute configuration of 8-amino-3,8-dideoxyoct-2-ulosonic acid, the chemical hallmark of lipopolysaccharides of the genus Shewanella

The novel monosaccharide 8-amino-3,8-dideoxyoct-2-ulosonic acid (Kdo8N) was isolated by methanolysis from the lipooligosaccharide of the marine Gram-negative bacterium Shewanella pacifica. After HPLC purification, the absolute configuration was determined by the Mosher ester method and proven to be 4R,5R,6R,7R. This established the D-manno-configuration of the monosaccharide.