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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 10671507
Publication DOI: 10.1074/jbc.275.7.4747
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: gibson

socrates.cgl.ucsf.edu
Institutions: Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Department of Microbiology, University of Iowa, Iowa City, Iowa 52242, Department of Microbiology, University of Oklahoma Health Sciences Center, Oklahoma City, Oklahoma 73104

Previously, we reported the expression of chimeric lipopolysaccharides (LPS) in Escherichia coli strain JM109 (a K-12 strain) transformed with plasmids containing Haemophilus influenzae lipooligosaccharide synthesis genes (lsg) (Abu Kwaik, Y., McLaughlin, R. E., Apicella, M. A., and Spinola, S. M. (1991) Mol. Microbiol. 5, 2475-2480). In this current study, we have analyzed the O-deacylated LPS and free oligosaccharides from three transformants (designated pGEMLOS-4, pGEMLOS-5, and pGEMLOS-7) by matrix-assisted laser desorption ionization, electrospray ionization, and tandem mass spectrometry techniques, along with composition and linkage analyses. These data show that the chimeric LPS consist of the complete E. coli LPS core structure glycosylated on the 7-position of the non-reducing terminal branch heptose with oligosaccharides from H. influenzae. In pGEMLOS-7, the disaccharide Gal 1→3 GlcNAc1→ is added, and in pGEMLOS-5, the structure is extended to Gal 1→4 GlcNAc 1→3 Gal 1→3 GlcNAc1→. PGEMLOS-5 LPS reacts positively with monoclonal antibody 3F11, an antibody that recognizes the terminal disaccharide of lacto-N-neotetraose. In pGEMLOS-4 LPS, the 3F11 epitope is apparently blocked by glycosylation on the 6-position of the terminal Gal with either Gal or GlcNAc. The biosynthesis of these chimeric LPS was found to be dependent on a functional wecA (formerly rfe) gene in E. coli. By using this carbohydrate expression system, we have been able to examine the functions of the lsg genes independent of the effects of other endogenous Haemophilus genes and expressed proteins.

Lipopolysaccharide, synthesis, Haemophilus, Haemophilus influenzae, lipopolysaccharides, Lipooligosaccharide, gene, strain, characterization, Escherichia, Escherichia coli

Structure type: oligomer
Location inside paper: Fig. 7
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130670,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391962,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_145003,IEDB_146664,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_167070,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_885811,IEDB_983931,SB_137,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_30,SB_7,SB_88

Methods: ESI-MS, MALDI-MS, MS/MS, composition analysis, linkage analysis
Biological activity: serological data
Biosynthesis and genetic data: genetic data
Comments, role: chimeric LPS from E. coli JM109 (K-12) transformed with plasmids containing Haemophilus influenzae LOS synthesis genes (lsg)

Related record ID(s): 4053, 4173, 4174, 4176, 4183
NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G50068GG, GlycomeDB:37717
Show glycosyltransferases

There are 2 chemically distinct structures. Please, select:

CC(=O)N[C@H]1C(OC[C@H]2OC(O[C@H]3[C@H](O)[C@@H](NC(C)=O)C(O[C@H]4[C@@H](O)[C@@H](CO)OC(O[C@H]5[C@H](O)[C@@H](CO)OC(OC[C@H](O)[C@H]6O[C@H](OC[C@H]7O[C@H](O[C@H]8[C@@H](O[C@@H]9[C@@H](O)[C@@H](O[C@@H]%10[C@H](O)[C@@H](O[C@@H]%11[C@H](O)[C@@H](O[C@H]%12[C@@H]([C@H](O)CO)OC(O)(C(=O)O)C[C@H]%12O)O[C@H]([C@@H](O)CO)[C@H]%11O)O[C@H]([C@@H](O)CO[C@H]%11O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]%11O)[C@H]%10O)O[C@H](CO[C@H]%10O[C@H](CO)[C@H](O)[C@H](O)[C@H]%10O)[C@H]9O)O[C@H](CO)[C@@H](O)[C@@H]8O)[C@H](O)[C@@H](O)[C@@H]7O)[C@@H](O)[C@@H](O)[C@@H]6O)[C@@H]5NC(C)=O)[C@@H]4O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize