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J. Biol. Chem., Vol. 275, Issue 36, 28006-28016, September 8, 2000
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From the Lipid A of Rhizobium etli CE3 differs
dramatically from that of other Gram-negative bacteria. Key features
include the presence of an unusual C28 acyl chain, a galacturonic acid
moiety at position 4', and an acylated aminogluconate unit in place of
the proximal glucosamine. In addition, R. etli lipid A is
reported to lack phosphate and acyloxyacyl residues. Most of these
remarkable structural claims are consistent with our recent enzymatic
studies. However, the proposed R. etli lipid A structure is
inconsistent with the ability of the precursor
(3-deoxy-D-manno-octulosonic
acid)2-4'-32P-lipid IVA to accept a
C28 chain in vitro (Brozek, K. A., Carlson, R. W., and Raetz, C. R. H. (1996) J. Biol.
Chem. 271, 32126-32136). To re-evaluate the structure, CE3 lipid
A was isolated by new chromatographic procedures. CE3 lipid A is now
resolved into six related components. Aminogluconate is present in D-1,
D-2, and E, whereas B and C contain the typical glucosamine
disaccharide seen in lipid A of most other bacteria. All the components
possess a peculiar acyloxyacyl moiety at position 2', which includes
the ester-linked C28 chain. As judged by mass spectrometry, the distal glucosamine units of A through E are the same, but the proximal units
are variable. As described in the accompanying article (Que, N. L. S., Ribeiro, A. A., and Raetz, C. R. H. (2000) J. Biol. Chem. 275, 28017-28027),
the discovery of component B suggests a plausible enzymatic pathway for
the biosynthesis of the aminogluconate residue found in species D-1,
D-2, and E of R. etli lipid A. We suggest that the unusual
lipid A species of R. etli might be essential during
symbiosis with leguminous host plants.
Purification and Mass Spectrometry of Six Lipid A Species from
the Bacterial Endosymbiont Rhizobium etli
DEMONSTRATION OF A CONSERVED DISTAL UNIT AND A VARIABLE PROXIMAL
PORTION*
,¶
Department of Biochemistry, Duke University
Medical Center, Durham, North Carolina 27710 and the
§ Middle Atlantic Mass Spectrometry Laboratory, Department
of Pharmacology and Molecular Sciences, The Johns Hopkins University
School of Medicine, Baltimore, Maryland 21205-2185
*
This work was supported by National Institutes of Health
Grants R37-GM-51796 (to C. R. H. R.) and GM-54882 (to
R. J. C.).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.
Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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