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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: urinary tract infections (UTI) [ICD11: GC08

]; infectious gastroenteritis [ICD11: 1A40.Z

]

The structure was elucidated in this paper
NCBI PubMed ID: 20471004
Publication DOI: 10.1016/j.carres.2010.04.005
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: A.A. Parhomchuk <lina_chuk

mail.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

The O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O12. Its structure was studied by sugar analysis using GLC of the alditol acetates and (S)-2-octyl glycosides, methylation analysis, Smith degradation, and (1)H and (13)C NMR spectroscopy, including 2D (1)H-(1)H COSY, TOCSY, ROESY, (1)H-(13)C HSQC, and HMBC experiments. It was found that the polymer is a neutral heteropolysaccharide and has a branched heptasaccharide repeating unit with the following structure: (formula, see text).

Lipopolysaccharide, O-antigen, Providencia alcalifaciens, polysaccharide structure

Structure type: oligomer
Location inside paper: p.1237, OS1
Contained glycoepitopes: IEDB_114709,IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391963,IEDB_141584,IEDB_141794,IEDB_143260,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation
Comments, role: O-polysaccharide after first Smith degradation; NMR for NAc are 1H 2.02-13; 13C 23.7-4.6 (CH3) and 174.5-76.2 (CO).

Related record ID(s): 25376, 25796
NCBI Taxonomy refs (TaxIDs): 126385
Reference(s) to other database(s): GlycomeDB:38080
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,2	Ac
2,3,4	bDGalpN	104.4	54.1	72.4	69.3	75.6	62.4
2,3	bDGalp	106.1	72.2	73.8	77.4	76.3	62.5
2,2	Ac
2	aDGalpN	100.2	50.4	78.0	70.2	72.4	62.5
	x?Thre-ol	62.2	81.1	72.5	63.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,2	Ac
2,3,4	bDGalpN	4.63	3.91	3.76	3.92	3.67	3.77
2,3	bDGalp	4.50	3.41	3.75	4.09	3.66	3.75-3.79
2,2	Ac
2	aDGalpN	5.03	4.36	4.06	4.20	4.14	3.77
	x?Thre-ol	3.80-3.83	3.75	3.93	3.65-3.70


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,4,2	Ac
2,3,4	bDGalpN	104.4/4.63	54.1/3.91	72.4/3.76	69.3/3.92	75.6/3.67	62.4/3.77
2,3	bDGalp	106.1/4.50	72.2/3.41	73.8/3.75	77.4/4.09	76.3/3.66	62.5/3.75-3.79
2,2	Ac
2	aDGalpN	100.2/5.03	50.4/4.36	78.0/4.06	70.2/4.20	72.4/4.14	62.5/3.77
	x?Thre-ol	62.2/3.80-3.83	81.1/3.75	72.5/3.93	63.7/3.65-3.70

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,2	Ac
2,3,4	bDGalpN	4.63	3.91	3.76	3.92	3.67	3.77
2,3	bDGalp	4.50	3.41	3.75	4.09	3.66	3.75 3.79
2,2	Ac
2	aDGalpN	5.03	4.36	4.06	4.20	4.14	3.77
	x?Thre-ol	3.80 3.83	3.75	3.93	3.65 3.70

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,2	Ac
2,3,4	bDGalpN	104.4	54.1	72.4	69.3	75.6	62.4
2,3	bDGalp	106.1	72.2	73.8	77.4	76.3	62.5
2,2	Ac
2	aDGalpN	100.2	50.4	78.0	70.2	72.4	62.5
	x?Thre-ol	62.2	81.1	72.5	63.7

There are 2 chemically distinct structures. Please, select:

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

SVG MW SMILES 3D mol Ionize