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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Enterobacter cloacae [ICD11: XN3YM

]

The structure was elucidated in this paper
NCBI PubMed ID: 23218327
Publication DOI: 10.1016/j.carbpol.2012.10.014
Journal NLM ID: 8307156
Publisher: Elsevier
Correspondence: Yizhen Wang <yzwang

zju.edu.cn>; yzwang321

zju.edu.cn
Institutions: College of Animal Science, Zhejiang University, Key Laboratory of Animal Nutrition and Feed Science, Ministry of Agriculture (East China), Zhejiang Provincial Laboratory of Feed and Animal Nutrition, Hangzhou, China

A novel high molecular weight (1.1 × 10(6)Da) exopolysaccharide (EPS) produced by Enterobacter cloacae Z0206 strain was isolated by column chromatography. Complete hydrolysis of the EPS followed by gas chromatography mass spectrometry (GC-MS) and high performance liquid chromatography (HPLC) analyses showed that the EPS is composed of L-fucose, D-glucose, D-galactose, D-glucuronic acid and pyruvic acid in the approximate molar ratio of 2:1:3:1:1. Partial acid hydrolysis of the purified EPS followed by gel permeation chromatography (GPC) yielded a hexasaccharide. A combination of chemical analysis coupled with mass spectrometry and 1D and 2D NMR spectroscopy applied to the oligosaccharide showed that the EPS comprises a heptasaccharide repeating unit.

hexasaccharide, NMR spectroscopy, structural analysis, mass spectrometry, Enterobacter cloacae Z0206

Structure type: oligomer
Location inside paper: p.508, fig.5, table 2
The structure in this paper was incorrect:

Original structure from CSDB record 3326

← originally published structure

Show legend

Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151528,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, partial acid hydrolysis, GC-MS, sugar analysis, ESI-MS, acid hydrolysis, Smith degradation, HPLC, GPC
Comments, role: hexasaccharide was obtained from partial acid hydrolysis of the EPS. Published considerations from NOESY support that bDGlcA substitutes C4, but not C3 of bDGlc; the same is reported in ref. [Verhoef et al., 2002]. The linkage position 3 between GlcpA and Glc was revised to 4 by CSDB staff, although it does not ideally fit the spectra too. The NMR signal of bDGlcA C1 (96.54) that seemed erroneous was removed by CSDB staff.

Related record ID(s): 3325
NCBI Taxonomy refs (TaxIDs): 550
Reference(s) to other database(s): GTC:G85866OW
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4	aDGalp	98.33	68.44	70.54	68.91	71.04	61.33
3,4	bDGlcpA	?	71.32	72.24	76.16	76.65	175.42
3	bDGlcp	103.86	73.31	76.36	75.40	76.07	61.38
4,4	bDGalp	102.76	73.83	69.81	68.91	69.47	60.62
4	aLFucp	100.44	69.18	72.51	78.49	67.59	15.35
	aLFucp	99.41	67.78	79.52	79.10	70.97	15.51


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4	aDGalp	5.420	3.730	3.892	3.893	4.195	3.620
3,4	bDGlcpA	4.532	3.452	3.640	3.708	3.345	-
3	bDGlcp	4.632	3.374	3.714	3.434	3.714	3.458-3.814
4,4	bDGalp	4.505	3.302	3.371	3.728	4.126	3.603
4	aLFucp	4.918	3.961	4.075	4.156	4.525	1.205
	aLFucp	5.268	3.880	3.880	3.737	3.761	1.247


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,4	aDGalp	98.33/5.420	68.44/3.730	70.54/3.892	68.91/3.893	71.04/4.195	61.33/3.620
3,4	bDGlcpA	?/4.532	71.32/3.452	72.24/3.640	76.16/3.708	76.65/3.345	
3	bDGlcp	103.86/4.632	73.31/3.374	76.36/3.714	75.40/3.434	76.07/3.714	61.38/3.458-3.814
4,4	bDGalp	102.76/4.505	73.83/3.302	69.81/3.371	68.91/3.728	69.47/4.126	60.62/3.603
4	aLFucp	100.44/4.918	69.18/3.961	72.51/4.075	78.49/4.156	67.59/4.525	15.35/1.205
	aLFucp	99.41/5.268	67.78/3.880	79.52/3.880	79.10/3.737	70.97/3.761	15.51/1.247

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4	aDGalp	5.420	3.730	3.892	3.893	4.195	3.620
3,4	bDGlcpA	4.532	3.452	3.640	3.708	3.345
3	bDGlcp	4.632	3.374	3.714	3.434	3.714	3.458 3.814
4,4	bDGalp	4.505	3.302	3.371	3.728	4.126	3.603
4	aLFucp	4.918	3.961	4.075	4.156	4.525	1.205
	aLFucp	5.268	3.880	3.880	3.737	3.761	1.247

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4	aDGalp	98.33	68.44	70.54	68.91	71.04	61.33
3,4	bDGlcpA	?	71.32	72.24	76.16	76.65	175.42
3	bDGlcp	103.86	73.31	76.36	75.40	76.07	61.38
4,4	bDGalp	102.76	73.83	69.81	68.91	69.47	60.62
4	aLFucp	100.44	69.18	72.51	78.49	67.59	15.35
	aLFucp	99.41	67.78	79.52	79.10	70.97	15.51

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@@H]2[C@H](C)O[C@@H](O)[C@@H](O)[C@@H]2O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](C(=O)O)[C@@H](O[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize