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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: 15155763
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: cwhitfie

uoguelph.ca
Institutions: Department of Microbiology, University of Guelph, Guelph, Ontario N1G 2W1

The type R3 core oligosaccharide predominates in the lipopolysaccharides from enterohemorrhagic E. coli isolates including O157:H7. The R3 core biosynthesis (waa) genetic locus contains two genes, waaD and waaJ, that are predicted to encode glycosyltransferases involved in completion of the outer core. Through determination of the structures of the lipopolysaccharide core in precise mutants and biochemical analyses of enzyme activities, WaaJ was shown to be a UDP-glucose:(galactosyl) LPS a-1,2-glucosyltransferase and WaaD a UDP-glucose:(glucosyl) LPS a-1,2-glucosyltransferase. The residue added by WaaJ was identified as the ligation site for O polysaccharide and this was confirmed by determination of the structure of the linkage region in serotype O157 lipopolysaccharide. The initial O157 repeat unit begins with a N-acetylgalactosamine residue in a -anomeric configuration, whereas the biological repeat unit for O157 contains a-linked N-acetylgalactosamine residues. With the characterization of WaaJ and WaaD, the activities of all of the enzymes encoded by the R3 waa locus are either known or predicted from homology data with a high level of confidence. However, when core oligosaccharide structure is considered, the origin of an additional a-1,3-linked N-acetylglucosamine residue in the outer core is unknown. The gene responsible for a non-stoichiometric a-1,7-linked N-acetylglucosamine substituent in the heptose (inner core) region was identified on the large virulence plasmids of E. coli O157 and Shigella flexneri serotype 2a. This is the first plasmid-encoded core oligosaccharide biosynthesis enzyme reported in E. coli.

Lipopolysaccharide, biosynthesis, gene, virulence, Escherichia coli O157:H7, core oligosaccharide, glycosyltransferases, plasmid

Structure type: oligomer
Location inside paper: Fig. 4, structure 4
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135394,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151528,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_983931,SB_192,SB_7,SB_86

Methods: 13C NMR, 1H NMR, EI-MS, methylation, NMR-2D, DNA sequencing, SDS-PAGE, MS/MS, composition analysis
Biosynthesis and genetic data: genetic data
Comments, role: oligosaccharide 4 isolated from N,O-deacylated E. coli CWG653 (serotype O157 wzy mutant) LPS by HPAEC

Related record ID(s): 9527, 9607, 9608, 9610
NCBI Taxonomy refs (TaxIDs): 83334
Reference(s) to other database(s): GlycomeDB:27591
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](N)[C@H](O[C@H]4[C@H](O)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O[C@@H]5[C@@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6N)[C@@H](O)[C@@H](CO)O[C@@H]5O[C@H]5[C@H](O)[C@@H](CO)O[C@H](O[C@@H]6[C@H](O)[C@@H](O[C@@H]7[C@H](O)[C@@H](O[C@@H]8[C@H](O[C@]9(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O9)C[C@](OC[C@H]9O[C@@H](OC[C@H]%10O[C@H](OP(=O)(O)O)[C@H](N)[C@@H](O)[C@@H]%10O)[C@H](N)[C@@H](O)[C@@H]9OP(=O)(O)O)(C(=O)O)O[C@@H]8[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]7OP(=O)(O)O)O[C@H]([C@@H](O)CO[C@H]7O[C@H]([C@@H](O)CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8N)[C@@H](O)[C@H](O)[C@@H]7O)[C@H]6O)[C@@H]5O)O[C@@H]4CO)O[C@H](CO)[C@@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O[C@H]2O[C@H](C)[C@@H](N)[C@H](O)[C@@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize