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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.8116, fig.2,table 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_130659,IEDB_130670,IEDB_140088,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226811,IEDB_423153,IEDB_983931,SB_192

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
Comments, role: Structure of the main oligosaccharide from deacylated E. coli B LPS.

Related record ID(s): 12874, 13055, 13056, 13057
NCBI Taxonomy refs (TaxIDs): 83333
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,4	aXKdop	174.3	101.8	35.2	65.7	66.7	72.1	70.7	62.9
0,6,6,5,3,3,3	aDGlcp	99.3	71.8	73.0	69.4	71.7	60.3
0,6,6,5,3,3	aDGlcp	99.9	70.5	80.0	70.4	72.0	60.29
0,6,6,5,3,7,7	bDGlcpA	102.1	73.0	75.5	71.7	75.6	175.8
0,6,6,5,3,7	aXLDmanHepp	101.6	70.0	70.4	66.2	71.9	67.3	71.7
0,6,6,5,3	aXLDmanHepp	101.8	69.2	77.9	65.9	72.2	68.4	71.2
0,6,6,5,4	P
0,6,6,5	aXLDmanHepp	98.8	71.0	75.2	69.1	73.0	68.8	63.0
0,6,6	aXKdop	174.7	99.5	34.2	70.8	68.0	72.3	69.5	63.8
0,6	bDGlcpN	103.7	56.4	76.0	69.9	74.3	61.6
0	aDGlcpN	94.5	55.5	73.5	69.8	71.2	69.0
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,4	aXKdop	-	-	1.752-2.112	4.132	4.019	3.624	3.973	3.657-3.909
0,6,6,5,3,3,3	aDGlcp	5.321	3.501	3.714	3.398	3.968	3.742-3.797
0,6,6,5,3,3	aDGlcp	5.246	3.605	3.887	3.560	3.856	3.667-3.885
0,6,6,5,3,7,7	bDGlcpA	4.460	3.307	3.471	3.469	3.683	-
0,6,6,5,3,7	aXLDmanHepp	4.820	3.949	3.834	3.825	3.648	4.173	3.849-3.946
0,6,6,5,3	aXLDmanHepp	5.241	4.406	4.014	3.948	3.604	4.115	3.662-3.734
0,6,6,5,4	P
0,6,6,5	aXLDmanHepp	5.188	3.995	4.035	4.315	4.225	4.128	3.768-3.944
0,6,6	aXKdop	-	-	1.859-2.179	4.112	4.182	3.583	3.814	3.520-3.871
0,6	bDGlcpN	4.345	2.687	3.262	3.436	3.516	3.437-3.531
0	aDGlcpN	5.334	2.637	3.564	3.416	4.008	3.750-4.180
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
0,6,6,4	aXKdop			35.2/1.752-2.112	65.7/4.132	66.7/4.019	72.1/3.624	70.7/3.973	62.9/3.657-3.909
0,6,6,5,3,3,3	aDGlcp	99.3/5.321	71.8/3.501	73.0/3.714	69.4/3.398	71.7/3.968	60.3/3.742-3.797
0,6,6,5,3,3	aDGlcp	99.9/5.246	70.5/3.605	80.0/3.887	70.4/3.560	72.0/3.856	60.29/3.667-3.885
0,6,6,5,3,7,7	bDGlcpA	102.1/4.460	73.0/3.307	75.5/3.471	71.7/3.469	75.6/3.683	
0,6,6,5,3,7	aXLDmanHepp	101.6/4.820	70.0/3.949	70.4/3.834	66.2/3.825	71.9/3.648	67.3/4.173	71.7/3.849-3.946
0,6,6,5,3	aXLDmanHepp	101.8/5.241	69.2/4.406	77.9/4.014	65.9/3.948	72.2/3.604	68.4/4.115	71.2/3.662-3.734
0,6,6,5,4	P
0,6,6,5	aXLDmanHepp	98.8/5.188	71.0/3.995	75.2/4.035	69.1/4.315	73.0/4.225	68.8/4.128	63.0/3.768-3.944
0,6,6	aXKdop			34.2/1.859-2.179	70.8/4.112	68.0/4.182	72.3/3.583	69.5/3.814	63.8/3.520-3.871
0,6	bDGlcpN	103.7/4.345	56.4/2.687	76.0/3.262	69.9/3.436	74.3/3.516	61.6/3.437-3.531
0	aDGlcpN	94.5/5.334	55.5/2.637	73.5/3.564	69.8/3.416	71.2/4.008	69.0/3.750-4.180
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,4	aXKdop			1.752 2.112	4.132	4.019	3.624	3.973	3.657 3.909
0,6,6,5,3,3,3	aDGlcp	5.321	3.501	3.714	3.398	3.968	3.742 3.797
0,6,6,5,3,3	aDGlcp	5.246	3.605	3.887	3.560	3.856	3.667 3.885
0,6,6,5,3,7,7	bDGlcpA	4.460	3.307	3.471	3.469	3.683
0,6,6,5,3,7	aXLDmanHepp	4.820	3.949	3.834	3.825	3.648	4.173	3.849 3.946
0,6,6,5,3	aXLDmanHepp	5.241	4.406	4.014	3.948	3.604	4.115	3.662 3.734
0,6,6,5,4	P
0,6,6,5	aXLDmanHepp	5.188	3.995	4.035	4.315	4.225	4.128	3.768 3.944
0,6,6	aXKdop			1.859 2.179	4.112	4.182	3.583	3.814	3.520 3.871
0,6	bDGlcpN	4.345	2.687	3.262	3.436	3.516	3.437 3.531
0	aDGlcpN	5.334	2.637	3.564	3.416	4.008	3.750 4.180
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,4	aXKdop	174.3	101.8	35.2	65.7	66.7	72.1	70.7	62.9
0,6,6,5,3,3,3	aDGlcp	99.3	71.8	73.0	69.4	71.7	60.3
0,6,6,5,3,3	aDGlcp	99.9	70.5	80.0	70.4	72.0	60.29
0,6,6,5,3,7,7	bDGlcpA	102.1	73.0	75.5	71.7	75.6	175.8
0,6,6,5,3,7	aXLDmanHepp	101.6	70.0	70.4	66.2	71.9	67.3	71.7
0,6,6,5,3	aXLDmanHepp	101.8	69.2	77.9	65.9	72.2	68.4	71.2
0,6,6,5,4	P
0,6,6,5	aXLDmanHepp	98.8	71.0	75.2	69.1	73.0	68.8	63.0
0,6,6	aXKdop	174.7	99.5	34.2	70.8	68.0	72.3	69.5	63.8
0,6	bDGlcpN	103.7	56.4	76.0	69.9	74.3	61.6
0	aDGlcpN	94.5	55.5	73.5	69.8	71.2	69.0
	P

There is only one chemically distinct structure:

N[C@H]1[C@H](OC[C@H]2O[C@H](OP(=O)(O)O)[C@H](N)[C@@H](O)[C@@H]2O)O[C@H](CO[C@]2(C(=O)O)C[C@@H](O[C@]3(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O3)[C@@H](O[C@H]3O[C@H]([C@@H](O)CO)[C@@H](OP(=O)(O)O)[C@H](O[C@H]4O[C@H]([C@@H](O)CO[C@H]5O[C@H]([C@@H](O)CO[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O)[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]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@@H]([C@H](O)CO)O2)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize