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J Biol Chem, Vol. 273, Issue 5, 2747-2757, January 30, 1998
The Structures of the Lipopolysaccharides from Rhizobium
etli Strains CE358 and CE359
THE COMPLETE STRUCTURE OF THE CORE REGION OF R. ETLI
LIPOPOLYSACCHARIDES
Lennart S.
Forsberg and
Russell W.
Carlson
From the Complex Carbohydrate Research Center, University of
Georgia, Athens, Georgia 30602
The structural arrangement of oligosaccharides
comprising the core region of Rhizobium etli CE3
lipopolysaccharide (LPS) has been elucidated through the
characterization of the LPSs from two R. etli mutants. One
mutant, CE358, completely lacks the O-chain polysaccharide,
while the second mutant, CE359, contains a truncated portion of this
polysaccharide. This structural arrangement of the core
oligosaccharides in these LPSs was determined using electrospray ionization mass spectrometry, tandem mass spectrometry, and methylation analysis. Mild acid hydrolysis of the CE359 LPS produces two major core
oligosaccharides: a tetrasaccharide (1) with the
structure -D-Galp-(1 6)-[ -D-GalpA-(1 4)]- -D-Manp-(1 5)-Kdop
(where Kdo represents
3-deoxy-D-manno-2-octulosonic acid) and a
trisaccharide (2) having the structure
-D-GalpA-(1 4)-[ -D-GalpA-(1 5)]-Kdop. Structure 1 in CE358 LPS lacks the
galacturonosyl residue. Glycosyl linkage and tandem mass spectrometry
analyses show that the intact LPS core region consists of trisaccharide
(2) attached to O-4 of the Kdo residue in tetrasaccharide
1, and that an additional Kdo residue is attached to O-6 of
the galactosyl residue of 1.
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The
additional terminally linked Kdo residue is not in close proximity to
the lipid A moiety, a unique location for a core Kdo residue. The
mutant LPS preparations also contain minor LPS species, one of which
lacks the Kdo linked to O-6 of the galactosyl residue, another that
lacks the galacturonic acid attached to O-5 of Kdo, and a third that
lacks two galacturonosyl residues and one Kdo residue. Thus, in
addition to lacking both heptose and phosphate, the R. etli
LPS core region differs substantially from the typical enterobacterial
cores. The abundance of galacturonosyl residues in the R. etli core might serve as a suitable functional replacement for phosphate, such as would be predicted for
Ca2+ binding.
Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.

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[Full Text]
[PDF]
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Copyright © 1998 by the American Society for Biochemistry and Molecular Biology.
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