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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Proteus mirabilis [ICD11: XN9ZF

]

The structure was elucidated in this paper
NCBI PubMed ID: 11082201
Publication DOI: 10.1046/j.1432-1033.2000.01793.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: rozala

biol.uni.lodz.pl
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Poland

The O-specific polysaccharide chains (O-antigens) of the lipopolysaccharides (LPSs) of Proteus mirabilis O48 and Proteus vulgaris O21 were found to have tetrasaccharide and pentasaccharide repeating units, respectively, interlinked by a glycosidic phosphate. Polysaccharides and an oligosaccharide were derived from the LPSs by various degradation procedures and studied by 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, H-detected 1H,13C and 1H,31P HMQC experiments. The following related structures of the repeating units of the O-antigens were established (top: Proteus mirabilis O48; bottom: Proteus vulgaris O21). The O-specific polysaccharide of P. vulgaris O21 has the same structure as that of Hafnia allvei 744 and PCM1194 [Petersson C., Jachymek, W., Klonowska, A., Lugowski, C., Niedziela, T. & Kenne, L. (1997) Eur. J. Biochem., 245, 668-675], except that the GlcN residue carries the N-acetyl rather than the N-[(R)-3-hydroxybutyryl] group. Serological investigations confirmed the close relatedness of the Proteus and Hafnia O-antigens studied.

Lipopolysaccharide, NMR, O-antigen, O-specific polysaccharide, Proteus, Proteus mirabilis, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose, Serological cross-reactivity

Structure type: polymer chemical repeating unit
Location inside paper: Fig.2
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_885822,SB_7

Methods: NMR-2D, EIA, ESI-MS, GLC, alkaline degradation, deamination, acid degradation, passive hemolysis test(PHT)
Biological activity: serological data

Related record ID(s): 107
NCBI Taxonomy refs (TaxIDs): 584
Reference(s) to other database(s): GTC:G44687OR, GlycomeDB:25062
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,4,2	Ac	175.9	23.1
0,2,3,4,3	Ac	175.3	21.3
0,2,3,4	aDGlcpN	99.2	53.2	74.2	68.3	71.9	65.0
0,2,3,2	Ac	175.9	23.1
0,2,3	aDGalpN	98.4	50.7	67.7	77.6	72.5	60.6
0,2,2	Ac	175.9	23.1
0,2	bDGlcpN	103.7	55.4	79.5	72.1	76.8	61.8
0	aDGalp	95.9	79.5	68.7	70.4	72.6	61.9
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,4,2	Ac	-	2.00
0,2,3,4,3	Ac	-	2.10
0,2,3,4	aDGlcpN	4.96	4.18	5.20	3.82	4.36	4.01-4.20
0,2,3,2	Ac	-	2.00
0,2,3	aDGalpN	5.43	4.26	3.93	4.07	3.91	3.68
0,2,2	Ac	-	2.00
0,2	bDGlcpN	4.68	3.81	3.72	3.63	3.40	3.70-3.86
0	aDGalp	5.78	3.80	3.92	4.00	4.07	3.70-3.85
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,2,3,4,2	Ac		23.1/2.00
0,2,3,4,3	Ac		21.3/2.10
0,2,3,4	aDGlcpN	99.2/4.96	53.2/4.18	74.2/5.20	68.3/3.82	71.9/4.36	65.0/4.01-4.20
0,2,3,2	Ac		23.1/2.00
0,2,3	aDGalpN	98.4/5.43	50.7/4.26	67.7/3.93	77.6/4.07	72.5/3.91	60.6/3.68
0,2,2	Ac		23.1/2.00
0,2	bDGlcpN	103.7/4.68	55.4/3.81	79.5/3.72	72.1/3.63	76.8/3.40	61.8/3.70-3.86
0	aDGalp	95.9/5.78	79.5/3.80	68.7/3.92	70.4/4.00	72.6/4.07	61.9/3.70-3.85
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,4,2	Ac		2.00
0,2,3,4,3	Ac		2.10
0,2,3,4	aDGlcpN	4.96	4.18	5.20	3.82	4.36	4.01 4.20
0,2,3,2	Ac		2.00
0,2,3	aDGalpN	5.43	4.26	3.93	4.07	3.91	3.68
0,2,2	Ac		2.00
0,2	bDGlcpN	4.68	3.81	3.72	3.63	3.40	3.70 3.86
0	aDGalp	5.78	3.80	3.92	4.00	4.07	3.70 3.85
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,4,2	Ac	175.9	23.1
0,2,3,4,3	Ac	175.3	21.3
0,2,3,4	aDGlcpN	99.2	53.2	74.2	68.3	71.9	65.0
0,2,3,2	Ac	175.9	23.1
0,2,3	aDGalpN	98.4	50.7	67.7	77.6	72.5	60.6
0,2,2	Ac	175.9	23.1
0,2	bDGlcpN	103.7	55.4	79.5	72.1	76.8	61.8
0	aDGalp	95.9	79.5	68.7	70.4	72.6	61.9
	P

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](O[C@H]2[C@@H](CO)O[C@H](O[C@H]3[C@H](O)[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]4OP([*])(=O)O)[C@@H]3NC(C)=O)[C@H](NC(C)=O)[C@H]2O)[C@H](NC(C)=O)[C@@H](OC(C)=O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Proteus vulgaris [ICD11: XN118

Lipopolysaccharide, NMR, O-antigen, O-specific polysaccharide, Proteus, Proteus mirabilis, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose, Serological cross-reactivity

Structure type: polymer chemical repeating unit
Location inside paper: Fig.2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192

Methods: NMR-2D, EIA, ESI-MS, GLC, alkaline degradation, deamination, acid degradation, passive hemolysis test(PHT)
Biological activity: serological data

Related record ID(s): 88, 21775
NCBI Taxonomy refs (TaxIDs): 585
Reference(s) to other database(s): GTC:G28341LC, GlycomeDB:25072
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,4,2	Ac	175.9	23.1
0,2,3,4	aDGlcpN	99.1	55.3	71.6	70.7	72.4	65.5
0,2,3,2	Ac	175.9	23.1
0,2,3,6	aDGlcp	100.0	72.4	74.5	70.7	73.4	62.5
0,2,3	aDGalpN	94.3	50.7	68.3	77.3	71.4	67.3
0,2,2	Ac	175.9	23.1
0,2	bDGalpN	103.8	52.2	75.9	65.0	76.7	61.6
0	aDGlcp	95.8	82.3	72.4	70.6	73.7	61.8
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,4,2	Ac	-	2.00
0,2,3,4	aDGlcpN	4.90	3.92	3.82	3.61	4.23	3.98-4.14
0,2,3,2	Ac	-	2.00
0,2,3,6	aDGlcp	4.80	3.55	3.62	3.43	3.60	3.62-3.84
0,2,3	aDGalpN	5.08	4.26	3.88	4.09	3.99	3.57-3.79
0,2,2	Ac	-	2.00
0,2	bDGalpN	4.67	4.06	3.73	4.03	3.59	3.73
0	aDGlcp	5.74	3.57	3.79	3.47	3.80	3.70-3.76
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,2,3,4,2	Ac		23.1/2.00
0,2,3,4	aDGlcpN	99.1/4.90	55.3/3.92	71.6/3.82	70.7/3.61	72.4/4.23	65.5/3.98-4.14
0,2,3,2	Ac		23.1/2.00
0,2,3,6	aDGlcp	100.0/4.80	72.4/3.55	74.5/3.62	70.7/3.43	73.4/3.60	62.5/3.62-3.84
0,2,3	aDGalpN	94.3/5.08	50.7/4.26	68.3/3.88	77.3/4.09	71.4/3.99	67.3/3.57-3.79
0,2,2	Ac		23.1/2.00
0,2	bDGalpN	103.8/4.67	52.2/4.06	75.9/3.73	65.0/4.03	76.7/3.59	61.6/3.73
0	aDGlcp	95.8/5.74	82.3/3.57	72.4/3.79	70.6/3.47	73.7/3.80	61.8/3.70-3.76
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,4,2	Ac		2.00
0,2,3,4	aDGlcpN	4.90	3.92	3.82	3.61	4.23	3.98 4.14
0,2,3,2	Ac		2.00
0,2,3,6	aDGlcp	4.80	3.55	3.62	3.43	3.60	3.62 3.84
0,2,3	aDGalpN	5.08	4.26	3.88	4.09	3.99	3.57 3.79
0,2,2	Ac		2.00
0,2	bDGalpN	4.67	4.06	3.73	4.03	3.59	3.73
0	aDGlcp	5.74	3.57	3.79	3.47	3.80	3.70 3.76
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,4,2	Ac	175.9	23.1
0,2,3,4	aDGlcpN	99.1	55.3	71.6	70.7	72.4	65.5
0,2,3,2	Ac	175.9	23.1
0,2,3,6	aDGlcp	100.0	72.4	74.5	70.7	73.4	62.5
0,2,3	aDGalpN	94.3	50.7	68.3	77.3	71.4	67.3
0,2,2	Ac	175.9	23.1
0,2	bDGalpN	103.8	52.2	75.9	65.0	76.7	61.6
0	aDGlcp	95.8	82.3	72.4	70.6	73.7	61.8
	P

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](O[C@H]2[C@@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O[C@H](O[C@@H]3[C@@H](NC(C)=O)[C@H](O[C@@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4OP([*])(=O)O)O[C@H](CO)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize