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The Biosynthesis of Cell Wall Lipopolysaccharide in Escherichia coli

III. THE ISOLATION AND CHARACTERIZATION OF 3-DEOXYOCTULOSONIC ACID

From the ¹ From the Rackham Arthritis Research Unit and the Department of Microbiology, The University of Michigan, Ann Arbor, Michigan, and the Department of Physiological Chemistry, The Johns Hopkins University School of Medicine, Baltimore, Maryland 21205

An acidic component of the cell wall lipopolysaccharide of Escherichia coli 0111-B₄ was isolated from mild acid hydrolysates of the polymer. It was concluded that this compound was 3-deoxy-D-manno-octulosonic acid on the basis of the following criteria: (a) paper chromatography in a variety of solvent systems; (b) degradation with ceric sulfate following borohydride reduction; (c) enzymatic degradation by 3-deoxyoctulosonate (KDO) aldolase to yield pyruvate and D-arabinose; (d) the rate of liberation of ß-formyl pyruvate by periodate oxidation; (e) chemical synthesis of crystalline penta-O-acetyl-KDO methyl ester, which, upon alkaline saponification, yielded KDO which corresponded chromatographically to KDO from lipopolysaccharide. Further, the product of saponification was identical with natural KDO with regard to the specificities of cytidine 5'-phosphate-KDO synthetase and KDO aldolase. The procedure employed for the chemical synthesis of KDO provides a method for the preparation of a chemically pure standard of this compound.

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