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Methyl 4-O-phosphono-and 4 -0 -(~-D-glucopyranosyl)-3-deoxy-~-D-erythro-2-hexulopyranosidonic acids, and 3-O-phosphono-, and 3-0-(~-D-glucopyranosyl)-2-deoxy-a-D-~f~~~~o-hexopyranoses have been synthesised and their behaviour in acidic media examined. At 100 "C, release of inorganic phosphate from the 4-O-phosphonohexulopyranosidonic acid is faster at pH 3-6 than at pH 0-1 and occurs through an elimination initiated by proton transfer. Phosphate release from the 3-O-phosphono-2-deoxy-hexopyranose occurs by a similar mechanism, but is much slower. Treatment at 100 "C with acetic acid of pH 3.4 causes release of glucosefrom the 4-O-glucosylated-3-deoxy-hexulopyranosidonic acid but not from the 3-O-glucosylated-2-deoxy-hexopyranose.STUDIES in this laboratory have shown that the Bordetellapertussis endotoxin is made up of two lipopolysaccharides, LPSl and LPS2,l in which lipid and polysaccharide regions are linked through the glycosidic bond of a 3deoxy-~-manno-2-octulopyranosonic acid (KDO) . While LPSl was rapidly hydrolysed by 0 . 0 1 ~ acetic acid (pH