Isolation and structural characterization of an 8‐O‐(4‐amino‐4‐deoxy‐ β‐l‐arabinopyranosyl)‐3‐deoxy‐d‐manno‐octulosonic acid disaccharide in the lipopolysaccharide of a Proteus mirabilis deep rough mutant

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Abstract
On short treatment of the lipopolysaccharide of a deep rough mutant of Proteus mirabilis (strain R45) with hydrochloric acid (0.01 M, 10 min, 100.degree.C) a compound was released which, on high-voltage paper electrophoresis, migrated slightly to the cathode (MGlcN = 0.19) and which stained with ninhydrin, alkaline silver nitrate and in the thiobarbituric acid assay. After purification and derivatization, its chemical structure was identified by combined gas-liquid chromatography/mass spectrometry and two-dimensional shift-correlated proton nuclear magnetic resonance spectroscopy as 8-O-(4-amino-4-deoxy-.beta.-L-arabinopyranosyl)-3-deoxy-D-manno-octulosonic acid. This disaccharide was also present in a wild-type strain of P. mirabilis.