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Originally published In Press as doi:10.1074/jbc.M004009200 on June 15, 2000

J. Biol. Chem., Vol. 275, Issue 36, 28017-28027, September 8, 2000
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Two-dimensional NMR Spectroscopy and Structures of Six Lipid A Species from Rhizobium etli CE3
DETECTION OF AN ACYLOXYACYL RESIDUE IN EACH COMPONENT AND ORIGIN OF THE AMINOGLUCONATE MOIETY*,

Nanette L. S. QueDagger , Anthony A. Ribeiro§, and Christian R. H. RaetzDagger

From the Dagger  Department of Biochemistry and the § Duke NMR Spectroscopy Center and Department of Radiology, Duke University Medical Center, Durham, North Carolina 27710

The chemical structures of six lipid A species (A, B, C, D-1, D-2, and E) purified from Rhizobium etli CE3 were investigated by one- and two-dimensional NMR spectroscopy. The R. etli lipid A subtypes each contain an unusual acyloxyacyl residue at position 2' as part of a conserved distal glucosamine moiety but differ in their proximal units. All R. etli lipid A species lack phosphate groups. However, they are derivatized with an alpha -linked galacturonic acid group at position 4', as shown by nuclear Overhauser effect spectroscopy. Component B, which had been not been reported in previous studies, features a beta , 1'-6 linked disaccharide of glucosamine acylated at positions 2, 3, 2', and 3' in a pattern that is typical of lipid A found in other Gram-negative bacteria. D-1 contains an acylated aminogluconate unit in place of the proximal glucosamine residue of B. C and E lack ester-linked beta -hydroxyacyl chains at position 3, as judged by their H-3 chemical shifts, and may be synthesized from B and D-1, respectively, by the R. etli 3-O-deacylase. D-2 is an isomer of D-1 that forms nonenzymatically by acyl chain migration. A may be an elimination product derived from D-1 during hydrolysis at 100 °C (pH 4.5), a step needed to release lipid A from lipopolysaccharide. Based on these findings, we propose a biosynthetic scheme for R. etli lipid A in which B is generated first by a variation of the E. coli pathway. The aminogluconate unit of D-1 could then be made from B by enzymatic oxidation of the proximal glucosamine. As predicted by our hypothesis, enzyme(s) can be demonstrated in extracts of R. etli that convert 14C-labeled B to D-1.

* This work was supported by National Institutes of Health Grant R37-GM-51796 (to C. R. H. R.). The Duke University NMR Center is supported in part by National Institutes of Health Grant P30-CA-14236. NMR instrumentation was also funded by grants from the National Science Foundation, the National Institutes of Health, the North Carolina Biotechnology Center, and Duke University.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

The on-line version of this article (available at http://www.jbc.org) contains additional figures.

To whom correspondence should be addressed: Dept. of Biochemistry, Duke University Medical Center, Box 3711, Durham, NC 27710. Tel.: 919-684-5326; Fax: 919-684-8885; E-mail: raetz@biochem.duke.edu.

Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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