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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: 23372159
Publication DOI: 10.1074/jbc.M112.445981
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: satish.raina

pg.gda.pl
Institutions: Leibniz-Center for Medicine and Biosciences, Parkallee 22, 23845 Borstel, Germany, Department of Microbiology, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland

It is well established that lipopolysaccharide (LPS) often carries nonstoichiometric substitutions in lipid A and in the inner core. In this work, the molecular basis of inner core alterations and their physiological significance are addressed. A new inner core modification of LPS is described, which arises due to the addition of glucuronic acid on the third heptose with a concomitant loss of phosphate on the second heptose. This was shown by chemical and structural analyses. Furthermore, the gene whose product is responsible for the addition of this sugar was identified in all Escherichia coli core types and in Salmonella and was designated waaH. Its deduced amino acid sequence exhibits homology to glycosyltransferase family 2. The transcription of the waaH gene is positively regulated by the PhoB/R two-component system in a growth phase-dependent manner, which is coordinated with the transcription of the ugd gene explaining the genetic basis of this modification. Glucuronic acid modification was observed in E. coli B, K12, R2, and R4 core types and in Salmonella. We also show that the phosphoethanolamine (P-EtN) addition on heptose I in E. coli K12 requires the product of the ORF yijP, a new gene designated as eptC. Incorporation of P-EtN is also positively regulated by PhoB/R, although it can occur at a basal level without a requirement for any regulatory inducible systems. This P-EtN modification is essential for resistance to a variety of factors, which destabilize the outer membrane like the addition of SDS or challenge to sublethal concentrations of Zn(2+).

oligosaccharide, Escherichia coli, glycosyltransferases, phosphoethanolamine, glucuronic acid, lipopolysaccharide (LPS), glycobiology

Structure type: oligomer
Location inside paper: p.8113, fig.1, glycoform I
Aglycon: (2->6) lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_130670,IEDB_133751,IEDB_136906,IEDB_137472,IEDB_140088,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_983931,SB_192,SB_7

Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, PCR, 31P NMR, ESI-MS, HPAEC, MALDI-MS, genetic methods, alkaline hydrolysis, extraction, transcription analysis, cloning, hydrazinolysis
Biosynthesis and genetic data: waaA, eptB, waaC,waaP,eptC, waaF,waaY, waaQ,waaG,waaB,waaO,waaR,waaU
Comments, role: glycoform I, proposed LPS structures from E. coli K12 in phosphate-limiting growth conditions.

Related record ID(s): 13055, 13056, 13057, 13058
NCBI Taxonomy refs (TaxIDs): 83333
Reference(s) to other database(s): GTC:G89391NP
Show glycosyltransferases

There is only one chemically distinct structure:

NCCOP(=O)(O)O[C@H](CO)[C@H]1O[C@@](O[C@@H]2C[C@](O)(C(=O)O)O[C@H]([C@H](O)CO)[C@@H]2O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](OP(=O)(O)OP(=O)(O)OCCN)[C@H](O[C@H]3O[C@H]([C@@H](O)CO[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](OP(=O)(O)O)[C@H](O[C@H]4O[C@H](CO[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@H]5O[C@H](CO[C@H]6O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@@H]3O)[C@@H]2O)(C(=O)O)C[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize