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J. Biol. Chem., Vol. 275, Issue 25, 18851-18863, June 23, 2000

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Structural Characterization of the O-antigenic Polysaccharide of the Lipopolysaccharide from Rhizobium etli Strain CE3
A UNIQUE O-ACETYLATED GLYCAN OF DISCRETE SIZE, CONTAINING 3-O-METHYL-6-DEOXY-L-TALOSE AND 2,3,4-TRI-O-METHYL-L-FUCOSE^*

Lennart S. Forsberg, U. Ramadas Bhat^§, and Russell W. Carlson^¶

From the  Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30602 and ^§ Miles-Cutter Laboratories, Berkeley, California 94701-1986

The O-antigenic polysaccharide of the Rhizobium etli CE3 lipopolysaccharide (LPS) was structurally characterized using chemical degradations (Smith degradation and -elimination of uronosyl residues) in combination with alkylation analysis, electrospray, and matrix-assisted laser desorption ionization-time of flight mass spectrometry, tandem mass spectrometry, and ¹H COSY and TOCSY nuclear magnetic resonance spectroscopy analyses of the native polysaccharide and the derived oligosaccharides. The polysaccharide was found to be a unique, relatively low molecular weight glycan having a fairly discrete size, with surprisingly little variation in the number of repeating units (degree of polymerization = 5). The polysaccharide is O-acetylated and contains a variety of O-methylated glycosyl residues, rendering the native glycan somewhat hydrophobic. The molecular mass of the major de-O-acetylated species, including the reducing end 3-deoxy-D-manno-2-octulosonic acid (Kdo) residue, is 3330 Da. The polysaccharide is comprised of a trisaccharide repeating unit having the structure 4)--D-GlcpA-(14)-[-3-O-Me-6-deoxy-Talp-(13)]--L-Fucp-(1. The nonreducing end of the glycan is terminated with the capping sequence -2,3,4-tri-O-Me-Fucp-(14)--D-GlcpA-(1, and the reducing end of the molecule consists of the non-repeating sequence 3)--L-Fucp-(13)--D-Manp-(13)--QuiNAcp-(14)--Kdop-(2, where QuiNAc is N-acetylquinovosamine (2-N-acetamido-2,6-dideoxyglucose). The reducing end Kdo residue links the O-chain polysaccharide to the core region oligosaccharide, resulting in a unique location for a Kdo residue in LPS, removed four residues distally from the lipid A moiety. Structural heterogeneity in the O-chain arises mainly from the O-acetyl and O-methyl substitution. Methylation analysis using trideuteriomethyl iodide indicates that a portion of the 2,3,4-tri-O-methylfucosyl capping residues, typically 15%, are replaced with 2-O-methyl- and/or 2,3-di-O-methylfucosyl residues. In addition, approximately 25% of the 3,4-linked branching fucosyl residues and 10% of the 3-linked fucosyl residues are 2-O-methylated. A majority of the glucuronosyl residues are methyl-esterified at C-6. These unique structural features may be significant in the infection process.

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