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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: neonatal necrotising enterocolitis [ICD11: KB88

, Life stage: neonatal]; bacteremia [ICD11: MA15.0

]; septicemia [ICD11: MA15.Y

]; meningitis [ICD11: 1D01

]

The structure was elucidated in this paper
NCBI PubMed ID: 25498203
Publication DOI: 10.1016/j.carres.2014.11.015
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Y.A. Knirel <yknirel

gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, College of Life Sciences, Nankai University, Tianjin, China, Tianjin Biochip Corporation, TEDA, Tianjin 300457

Cronobacter spp. are emerging opportunistic human pathogens linked with life-threatening infections predominantly in neonates. O-Antigen (O-polysaccharide) is highly variable and plays an important role in virulence and niche adaptation. In this work, short-chain O-polysaccharides consisting on the average of 2-3 repeating units were obtained by mild acid or mild alkaline degradation of the lipopolysaccharides of C. dublinensis G3983 and G3977 and studied by composition analysis, Smith degradation, and (1)H and (13)C NMR spectroscopy. The following structures of the O-polysaccharides were established: [Formula: see text] where R indicates H in strain G3983 or ?-D-Glcp in strain G3977, d-Fuc3NAlaAc indicates 3-(N-acetyl-L-alanyl)amino-3,6-dideoxy-D-galactose. Both strains share the O-antigen gene cluster, which is identical to that of C. dublinensis O1 (Foodborne Pathog. Dis.2013, 10, 343-352). The assigned gene functions are in agreement with the O-antigen structure of C. dublinensis G3983, and the side-chain glucosylation of the O-antigen of C. dublinensis G3977 is evidently encoded elsewhere in the genome.

Lipopolysaccharide, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster, Cronobacter dublinensis

Structure type: fragment of a bigger structure
Location inside paper: p.135, chart 1, table 1 PS3983
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_140629,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_423115,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, GLC, mild acid hydrolysis, Smith degradation, mild alkaline degradation, NMR-1D, HPLC, GPC, analysis of genes
Comments, role: terminal non-reducing O-unit

Related record ID(s): 30582, 30909, 30910, 30911, 30912, 30913
NCBI Taxonomy refs (TaxIDs): 413497
Show glycosyltransferases

NMR conditions: in D2O at 303 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,4,3,2	Ac	175.1-175.8	22.7-23.5
3,4,4,4,3	xLAla?	176.6-176.7	51.0-51.2	18.1
3,4,4,4	aDFucp3N	100.9	67.4	52.6	71.7	68.4	16.4
3,4,4	bDGalp	104.4	72.0	73.2	78.0	76.8	61.3
3,4	aDGlcp
3	bDGlcp
2	Ac
	bDGalpN


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,4,3,2	Ac	-	2.01-2.05
3,4,4,4,3	xLAla?	-	4.33-4.36	1.38-1.40
3,4,4,4	aDFucp3N	4.87	3.79	4.18	3.77	4.53	1.14
3,4,4	bDGalp	4.48	3.65	3.75	3.99	3.76	3.76-3.89
3,4	aDGlcp
3	bDGlcp
2	Ac
	bDGalpN


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,4,4,3,2	Ac		22.7-23.5/2.01-2.05
3,4,4,4,3	xLAla?		51.0-51.2/4.33-4.36	18.1/1.38-1.40
3,4,4,4	aDFucp3N	100.9/4.87	67.4/3.79	52.6/4.18	71.7/3.77	68.4/4.53	16.4/1.14
3,4,4	bDGalp	104.4/4.48	72.0/3.65	73.2/3.75	78.0/3.99	76.8/3.76	61.3/3.76-3.89
3,4	aDGlcp
3	bDGlcp
2	Ac
	bDGalpN

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,4,3,2	Ac		2.01 2.05
3,4,4,4,3	xLAla?		4.33 4.36	1.38 1.40
3,4,4,4	aDFucp3N	4.87	3.79	4.18	3.77	4.53	1.14
3,4,4	bDGalp	4.48	3.65	3.75	3.99	3.76	3.76 3.89
3,4	aDGlcp
3	bDGlcp
2	Ac
	bDGalpN

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,4,3,2	Ac	175.1 175.8	22.7 23.5
3,4,4,4,3	xLAla?	176.6 176.7	51.0 51.2	18.1
3,4,4,4	aDFucp3N	100.9	67.4	52.6	71.7	68.4	16.4
3,4,4	bDGalp	104.4	72.0	73.2	78.0	76.8	61.3
3,4	aDGlcp
3	bDGlcp
2	Ac
	bDGalpN

There is only one chemically distinct structure:

CC(=O)N[C@@H](C)C(=O)N[C@H]1[C@@H](O)[C@@H](C)O[C@H](O[C@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@@H](O[C@H]5[C@@H](O)[C@@H](CO)O[C@@H](O)[C@@H]5NC(C)=O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize