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Volume 271, Number 50, Issue of December 13, 1996 pp. 32112-32118
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

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Lipopolysaccharide Biosynthesis in Rhizobium leguminosarum
NOVEL ENZYMES THAT PROCESS PRECURSORS CONTAINING 3-DEOXY-D-MANNO-OCTULOSONIC ACID

(Received for publication, May 21, 1996, and in revised form, August 21, 1996)

From the Department of Biochemistry, Duke University Medical Center, Durham, North Carolina 27710

The lipopolysaccharide of Rhizobium leguminosarum differs from that of other Gram-negative organisms. R. leguminosarum lipid A lacks phosphate groups, but it contains a galacturonic acid residue at the 4-position and an aminogluconate moiety in place of the usual glucosamine 1-phosphate unit. R. leguminosarum lipid A is esterified with a peculiar long chain fatty acid, 27-hydroxyoctacosanoate, not found in enteric Gram-negative bacteria, and the inner core of R. leguminosarum contains mannose and galactose in place of heptose. Despite these differences, the biosynthesis of R. leguminosarum lipid A is initiated by the same seven enzyme pathway as in Escherichia coli (Raetz, C. R. H. (1993) J. Bacteriol. 175, 5745-5753) to form the phosphorylated precursor, (Kdo)₂-lipid IV_A, which is then processed differently. We now describe several novel Rhizobium-specific enzymes that recognize and modify (Kdo)₂-lipid IV_A. The 1- and 4-phosphatases were detected using (Kdo)₂-[1-³²P]-lipid IV_A and (Kdo)₂-[4-³²P]-lipid IV_A, respectively, as shown by release of ³²P_i. In the presence of GDP-mannose and/or UDP-galactose, membranes of R. leguminosarum first transferred mannose and then galactose to (Kdo)₂-[4-³²P]-lipid IV_A. In addition, at least two hydrophobic metabolites were generated from (Kdo)₂-[4-³²P]-lipid IV_A in a manner that was dependent upon both membranes and a cytosolic factor from R. leguminosarum. These compounds are attributed to novel acylations of (Kdo)₂-[4-³²P]-lipid IV_A. E. coli membranes and cytosol did not catalyze any of the unique reactions detected in R. leguminosarum extracts. Our findings establish the conservation and versatility of (Kdo)₂-lipid IV_A as a lipid A precursor in bacteria.

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