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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: infection due to Enterococcus faecalis [ICD11: XN2H4

]

The structure was elucidated in this paper
NCBI PubMed ID: 22551470
Publication DOI: 10.1016/j.carres.2012.03.031
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Z. Kaczyński <zbyszek

chem.univ.gda.pl>
Institutions: Center for Infectious Diseases and Travel Medicine, Department of Medicine, University Medical Center Freiburg, Hugstetter Strasse 55, D-79106 Freiburg i. Br., Germany

Wall teichoic acid (WTA) was isolated from Enterococcus faecalis 12030, a clinical isolate and biofilm-producing strain, and analyzed using compositional chemical methods, nuclear magnetic resonance spectroscopy, and mass spectrometry. The repeating units of WTA were composed of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-galactose, 2-acetamido-2-deoxy-D-glucose, D-ribitol, and phosphate in a molar ratio 1:2:1:1:1:1, and had the structure given below.

NMR, structure, polysaccharide, Enterococcus faecalis, wall teichoic acid

Structure type: oligomer
Location inside paper: p.109, table 2
Compound class: teichoic acid
Contained glycoepitopes: IEDB_114703,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_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, sugar analysis, 31P NMR, ESI-MS, GLC, chemical methods, GPC, HF treatment
Comments, role: OS odtained after dephosphorylation of the wall teichoic acid.

Related record ID(s): 27337
NCBI Taxonomy refs (TaxIDs): 1169282
Reference(s) to other database(s): GTC:G28540EY
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
1,3,6,3	bDGalp	106.08	71.96	73.82	69.99	73.44	62.25
1,3,6,2	Ac
1,3,6	bDGalpN	103.18	52.52	80.95	68.50	76.35	62.25
1,3,2	Ac
1,3	aDGlcpN	95.27	54.71	72.17	71.08	72.04	69.41
1,6	aDGlcp	99.47	72.55	74.33	70.87	73.15	61.79
1	bDGalp	104.07	70.66	78.29	66.14	74.11	67.92
	xDRib-ol	71.97	71.71	72.98	72.17	63.71


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
1,3,6,3	bDGalp	4.459	3.531	3.611	3.909	3.843	3.757-3.757
1,3,6,2	Ac
1,3,6	bDGalpN	4.552	4.044	3.911	4.237	3.666	3.757-3.757
1,3,2	Ac
1,3	aDGlcpN	5.031	3.945	3.821	3.522	4.065	3.830-4.109
1,6	aDGlcp	4.959	3.567	3.697	3.424	3.746	3.761-3.864
1	bDGalp	4.493	3.641	3.712	4.086	3.912	3.755-3.944
	xDRib-ol	3.930-4.040	3.999	3.747	3.821	3.655-3.815


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
1,3,6,3	bDGalp	106.08/4.459	71.96/3.531	73.82/3.611	69.99/3.909	73.44/3.843	62.25/3.757-3.757
1,3,6,2	Ac
1,3,6	bDGalpN	103.18/4.552	52.52/4.044	80.95/3.911	68.50/4.237	76.35/3.666	62.25/3.757-3.757
1,3,2	Ac
1,3	aDGlcpN	95.27/5.031	54.71/3.945	72.17/3.821	71.08/3.522	72.04/4.065	69.41/3.830-4.109
1,6	aDGlcp	99.47/4.959	72.55/3.567	74.33/3.697	70.87/3.424	73.15/3.746	61.79/3.761-3.864
1	bDGalp	104.07/4.493	70.66/3.641	78.29/3.712	66.14/4.086	74.11/3.912	67.92/3.755-3.944
	xDRib-ol	71.97/3.930-4.040	71.71/3.999	72.98/3.747	72.17/3.821	63.71/3.655-3.815

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
1,3,6,3	bDGalp	4.459	3.531	3.611	3.909	3.843	3.757 3.757
1,3,6,2	Ac
1,3,6	bDGalpN	4.552	4.044	3.911	4.237	3.666	3.757 3.757
1,3,2	Ac
1,3	aDGlcpN	5.031	3.945	3.821	3.522	4.065	3.830 4.109
1,6	aDGlcp	4.959	3.567	3.697	3.424	3.746	3.761 3.864
1	bDGalp	4.493	3.641	3.712	4.086	3.912	3.755 3.944
	xDRib-ol	3.930 4.040	3.999	3.747	3.821	3.655 3.815

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
1,3,6,3	bDGalp	106.08	71.96	73.82	69.99	73.44	62.25
1,3,6,2	Ac
1,3,6	bDGalpN	103.18	52.52	80.95	68.50	76.35	62.25
1,3,2	Ac
1,3	aDGlcpN	95.27	54.71	72.17	71.08	72.04	69.41
1,6	aDGlcp	99.47	72.55	74.33	70.87	73.15	61.79
1	bDGalp	104.07	70.66	78.29	66.14	74.11	67.92
	xDRib-ol	71.97	71.71	72.98	72.17	63.71

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize