Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides
10.1128/jb.179.20.6453-6463.1997
Crossref journal-article
American Society for Microbiology
Journal of Bacteriology (235)
Abstract

The chemical structure of free lipid A isolated from rough- and smooth-form lipopolysaccharides (R-LPS and S-LPS, respectively) of the human gastroduodenal pathogen Helicobacter pylori was elucidated by compositional and degradative analysis, nuclear magnetic resonance spectroscopy, and mass spectrometry. The predominant molecular species in both lipid A components are identical and tetraacylated, but a second molecular species which is hexaacylated is also present in lipid A from S-LPS. Despite differences in substitution by acyl chains, the hydrophilic backbone of the molecules consisted of beta(1,6)-linked D-glucosamine (GlcN) disaccharide 1-phosphate. Because of microheterogeneity, nonstoichiometric amounts of ethanolamine-phosphate were also linked to the glycosidic hydroxyl group. In S-LPS, but not in R-LPS, the hydroxyl group at position 4' was partially substituted by another phosphate group. Considerable variation in the distribution of fatty acids on the lipid A backbone was revealed by laser desorption mass spectrometry. In tetraacyl lipid A, the amino group of the reducing GlcN carried (R)-3-hydroxyoctadecanoic acid (position 2), that of the nonreducing GlcN carried (R)-3-(octadecanoyloxy)octadecanoic acid (position 2'), and ester-bound (R)-3-hydroxyhexadecanoic acid was attached at position 3. Hexaacyl lipid A had a similar substitution by fatty acids, but in addition, ester-bound (R)-3-(dodecanoyloxy)hexadecanoic acid or (R)-3(tetradecanoyloxy)hexadecanoic acid was attached at position 3'. The predominant absence of ester-bound 4'-phosphate and the presence of tetraacyl lipid A with fatty acids of 16 to 18 carbons in length differentiate H. pylori lipid A from that of other bacterial species and help explain the low endotoxic and biological activities of H. pylori LPS.

Bibliography

Moran, A. P., Lindner, B., & Walsh, E. J. (1997). Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides. Journal of Bacteriology, 179(20), 6453–6463.

Authors 3
  1. A P Moran (first)
  2. B Lindner (additional)
  3. E J Walsh (additional)
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Dates
Type When
Created 8 years, 9 months ago (Nov. 10, 2016, 10:42 a.m.)
Deposited 2 months, 3 weeks ago (June 12, 2025, 6:21 a.m.)
Indexed 2 months ago (July 3, 2025, 4:45 a.m.)
Issued 27 years, 11 months ago (Oct. 1, 1997)
Published 27 years, 11 months ago (Oct. 1, 1997)
Published Print 27 years, 11 months ago (Oct. 1, 1997)
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@article{Moran_1997, title={Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides}, volume={179}, ISSN={1098-5530}, url={http://dx.doi.org/10.1128/jb.179.20.6453-6463.1997}, DOI={10.1128/jb.179.20.6453-6463.1997}, number={20}, journal={Journal of Bacteriology}, publisher={American Society for Microbiology}, author={Moran, A P and Lindner, B and Walsh, E J}, year={1997}, month=oct, pages={6453–6463} }