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Taxonomic group: bacteria / Chlamydiae (Phylum: Chlamydiae)
Associated disease: infection due to Chlamydia trachomatis [ICD11: XN4Q4

]

The structure was elucidated in this paper
NCBI PubMed ID: 10358025
Publication DOI: 10.1074/jbc.274.24.16819
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: hbrade

fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, D-23845 Borstel, Germany

The lipopolysaccharide (LPS) of Chlamydia trachomatis L2 was isolated from tissue culture-grown elementary bodies using a modified phenol/water procedure followed by extraction with phenol/chloroform/light petroleum. From a total of 5 x 10(4) cm2 of infected monolayers, 22.3 mg of LPS were obtained. Compositional analysis indicated the presence of 3-deoxy-D-manno-oct-2-ulopyranosonic acid (Kdo), GlcN, phosphorus, and fatty acids in a molar ratio of 2.8:2:2.1:4.5. Matrix-assisted laser-desorption ionization mass spectrometry performed on the de-O-acylated LPS gave a major molecular ion peak at m/z 1781.1 corresponding to a molecule of 3 Kdo, 2 GlcN, 2 phosphates, and two 3-hydroxyeicosanoic acid residues. The structure of deacylated LPS obtained after successive treatment with hydrazine and potassium hydroxide was determined by 600 MHz NMR spectroscopy as Kdo α2→8 Kdo α2→4 Kdo α2→6 DGlcpN β1→6 DGlcpNα 1,4'-bisphosphate. These data, together with those published recently on the acylation pattern of chlamydial lipid A (Qureshi, N., Kaltashov, I., Walker, K., Doroshenko, V., Cotter, R. J., Takayama, K, Sievert, T. R., Rice, P. A., Lin, J.-S. L., and Golenbock, D. T. (1997) J. Biol. Chem. 272, 10594-10600) allow us to present for the first time the complete structure of a major molecular species of a chlamydial LPS

Lipopolysaccharide, structural, serotype, analysis, Chlamydia, Chlamydia trachomatis, structural analysis

Structure type: oligomer
Location inside paper: Fig.4
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_135394,IEDB_141807,IEDB_150760,IEDB_150908,IEDB_151531

Methods: 13C NMR, 1H NMR, NMR-2D, MALDI-MS
Biological activity: Chlamydia are obligatory intracellular bacteria causing acute and chronic infections in animals and humans. Chlamydia trachomatis is a predominant pathogen in sexually transmitted urogenital infections in developed countries and is considered as the major cause of secondary infertility in women resulting from tubal damage and occlusion.
Comments, role: de-O-acylated lipopolysaccharide from C. trachomatis L2

Related record ID(s): 4382
NCBI Taxonomy refs (TaxIDs): 813
Show glycosyltransferases

There is only one chemically distinct structure:

CCCCCCCCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO[C@]3(C(=O)O)C[C@@H](O[C@]4(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO[C@]5(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O5)O4)[C@@H](O)[C@@H]([C@H](O)CO)O3)[C@@H](OP(=O)(O)O)[C@H](O)[C@H]2NC(=O)C[C@H](O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize