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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Citrobacter [ICD11: XN0FZ

]

The structure was elucidated in this paper
NCBI PubMed ID: 7744044
Publication DOI: 10.1111/j.1432-1033.1995.0299l.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Max-Planck-Institut fur Medizinische Forschung, Heidelberg, Germany

Sugar analysis of the O-specific polysaccharide produced by Citrobacter serotype O41 revealed the presence of a hexasaccharide repeating unit, which includes the unusual 3-amino-N-(D-3'-hydroxybutyryl)-3,6-dideoxy-D-galactosyl residue (Fuc3NAcyl). The structure of the repeating unit was determined by extensive use of homo- and heteronuclear two-dimensional NMR spectroscopy, including the application of long-range 1H-13C correlation experiments and NOE studies to establish the sequence of sugar units. Indentification of the Glc β1→2 Fuc3NAcyl β1→6 GlcNAc α1→ sequence at the non-reducing terminus establishes the biological repeating unit of this O-specific polysaccharide as: →2 Glc β1→ Fuc3NAcyl β1→6 GlcNAc α1→ (Glc α1→2) 4Gal β1→3 GalNAc β1→. This structure is similar to that found for the O-specific polysaccharide isolated from Hafnia alvei strain 1211 [Katzenellenbogen, E., Romanowska, E., Dabrowski, U. & Dabrowski, J. (1991) Eur. J. Biochem. 200, 401-407], which differs in having an acetyl substituent at O4 of the Fuc3NAcyl residue and a branch point of GalNAc α substituted by Glc β at O3; these differences are responsible for the only weak serological cross-reactivity of the two strains.

Lipopolysaccharide, 6-dideoxy-D-galactose, endotoxin, Citrobacter, 3-amino-N-(D-3'-hydroxybutyryl)-3

Structure type: polymer biological repeating unit
Location inside paper: p.299, p.301, p.304
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_147450,IEDB_151531,IEDB_153217,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_88

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D
Biosynthesis and genetic data: genetic data

Related record ID(s): 124717
NCBI Taxonomy refs (TaxIDs): 544
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,6,2	bDGlcp	101.39	82.28	71.17	71.12	76.98	62.23
3,4,6,3	lR3HOBut	174.62	45.59	65.78	23.19
3,4,6	bDFucp3N	103.65	74.37	55.61	71.37	72.75	16.17
3,4,2	Ac	175.04	22.13
3,4	aDGlcpN	99.63	54.94	71.12	69.65	71.97	68.92
3,2	aDGlc?	97.10	72.56	73.60	70.45	72.67	61.69
3	bDGalp	104.58	73.60	71.58	78.62	76.29	60.92
2	Ac	175.51	23.54
	bDGalpN	103.16	52.55	80.06	68.81	75.31	62.05


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,6,2	bDGlcp	4.687	3.436	3.461	3.36	3.38	3.71-3.90
3,4,6,3	lR3HOBut	-	2.442-2.706	4.306	1.281
3,4,6	bDFucp3N	4.537	3.866	4.229	3.628	3.863	1.242
3,4,2	Ac	-	2.087
3,4	aDGlcpN	4.846	3.926	3.842	3.918	4.321	3.918-4.069
3,2	aDGlc?	5.353	3.504	3.776	3.389	3.998	3.72-3.82
3	bDGalp	4.710	3.80	3.80	3.961	3.746	3.73-3.78
2	Ac	-	2.048
	bDGalpN	4.700	4.008	3.958	4.134	3.668	3.72-3.88


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,6,2	bDGlcp	101.39/4.687	82.28/3.436	71.17/3.461	71.12/3.36	76.98/3.38	62.23/3.71-3.90
3,4,6,3	lR3HOBut		45.59/2.442-2.706	65.78/4.306	23.19/1.281
3,4,6	bDFucp3N	103.65/4.537	74.37/3.866	55.61/4.229	71.37/3.628	72.75/3.863	16.17/1.242
3,4,2	Ac		22.13/2.087
3,4	aDGlcpN	99.63/4.846	54.94/3.926	71.12/3.842	69.65/3.918	71.97/4.321	68.92/3.918-4.069
3,2	aDGlc?	97.10/5.353	72.56/3.504	73.60/3.776	70.45/3.389	72.67/3.998	61.69/3.72-3.82
3	bDGalp	104.58/4.710	73.60/3.80	71.58/3.80	78.62/3.961	76.29/3.746	60.92/3.73-3.78
2	Ac		23.54/2.048
	bDGalpN	103.16/4.700	52.55/4.008	80.06/3.958	68.81/4.134	75.31/3.668	62.05/3.72-3.88

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,6,2	bDGlcp	4.687	3.436	3.461	3.36	3.38	3.71 3.90
3,4,6,3	lR3HOBut		2.442 2.706	4.306	1.281
3,4,6	bDFucp3N	4.537	3.866	4.229	3.628	3.863	1.242
3,4,2	Ac		2.087
3,4	aDGlcpN	4.846	3.926	3.842	3.918	4.321	3.918 4.069
3,2	aDGlc?	5.353	3.504	3.776	3.389	3.998	3.72 3.82
3	bDGalp	4.710	3.80	3.80	3.961	3.746	3.73 3.78
2	Ac		2.048
	bDGalpN	4.700	4.008	3.958	4.134	3.668	3.72 3.88

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,6,2	bDGlcp	101.39	82.28	71.17	71.12	76.98	62.23
3,4,6,3	lR3HOBut	174.62	45.59	65.78	23.19
3,4,6	bDFucp3N	103.65	74.37	55.61	71.37	72.75	16.17
3,4,2	Ac	175.04	22.13
3,4	aDGlcpN	99.63	54.94	71.12	69.65	71.97	68.92
3,2	aDGlc?	97.10	72.56	73.60	70.45	72.67	61.69
3	bDGalp	104.58	73.60	71.58	78.62	76.29	60.92
2	Ac	175.51	23.54
	bDGalpN	103.16	52.55	80.06	68.81	75.31	62.05

There are 2 chemically distinct structures. Please, select:

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

SVG MW SMILES 3D mol Ionize