CSDB: Search results

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: polymer chemical repeating unit
Location inside paper: abstract
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_591403,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

Related record ID(s): 28660
NCBI Taxonomy refs (TaxIDs): 1169282
Reference(s) to other database(s): GTC:G65620PC
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,1,3,6,3	bDGalp	106.07	71.94	73.78	69.48	74.68	65.34
0,1,3,6,2	Ac
0,1,3,6	bDGalpN	103.14	52.51	81.03	69.65	76.38	62.37
0,1,3,2	Ac
0,1,3	aDGlcpN	95.17	54.73	72.54	71.08	71.91	69.12
0,1,6	aDGlcp	99.38	72.87	74.42	70.90	73.16	61.88
0,1	bDGalp	104.20	70.73	78.29	66.18	74.22	68.12
0	xDRib-ol	71.93	72.08	72.98	72.38	67.87
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,1,3,6,3	bDGalp	4.488	3.547	3.649	3.993	3.836	4.025-4.025
0,1,3,6,2	Ac	-	2.075
0,1,3,6	bDGalpN	4.544	4.057	3.924	4.228	3.677	3.746-3.810
0,1,3,2	Ac	-	2.087
0,1,3	aDGlcpN	5.037	3.937	3.834	3.542	4.055	3.850-4.104
0,1,6	aDGlcp	4.973	3.571	3.728	3.436	3.765	3.779-3.870
0,1	bDGalp	4.496	3.662	3.714	4.088	3.920	3.774-3.953
0	xDRib-ol	3.939-3.939	3.971	3.921	3.843	3.981-4.082
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,1,3,6,3	bDGalp	106.07/4.488	71.94/3.547	73.78/3.649	69.48/3.993	74.68/3.836	65.34/4.025-4.025
0,1,3,6,2	Ac	NMR TSV error 2: unequal length of 13C and 1H datasets
0,1,3,6	bDGalpN	103.14/4.544	52.51/4.057	81.03/3.924	69.65/4.228	76.38/3.677	62.37/3.746-3.810
0,1,3,2	Ac	NMR TSV error 2: unequal length of 13C and 1H datasets
0,1,3	aDGlcpN	95.17/5.037	54.73/3.937	72.54/3.834	71.08/3.542	71.91/4.055	69.12/3.850-4.104
0,1,6	aDGlcp	99.38/4.973	72.87/3.571	74.42/3.728	70.90/3.436	73.16/3.765	61.88/3.779-3.870
0,1	bDGalp	104.20/4.496	70.73/3.662	78.29/3.714	66.18/4.088	74.22/3.920	68.12/3.774-3.953
0	xDRib-ol	71.93/3.939-3.939	72.08/3.971	72.98/3.921	72.38/3.843	67.87/3.981-4.082
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,1,3,6,3	bDGalp	4.488	3.547	3.649	3.993	3.836	4.025 4.025
0,1,3,6,2	Ac		2.075
0,1,3,6	bDGalpN	4.544	4.057	3.924	4.228	3.677	3.746 3.810
0,1,3,2	Ac		2.087
0,1,3	aDGlcpN	5.037	3.937	3.834	3.542	4.055	3.850 4.104
0,1,6	aDGlcp	4.973	3.571	3.728	3.436	3.765	3.779 3.870
0,1	bDGalp	4.496	3.662	3.714	4.088	3.920	3.774 3.953
0	xDRib-ol	3.939 3.939	3.971	3.921	3.843	3.981 4.082
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,1,3,6,3	bDGalp	106.07	71.94	73.78	69.48	74.68	65.34
0,1,3,6,2	Ac
0,1,3,6	bDGalpN	103.14	52.51	81.03	69.65	76.38	62.37
0,1,3,2	Ac
0,1,3	aDGlcpN	95.17	54.73	72.54	71.08	71.91	69.12
0,1,6	aDGlcp	99.38	72.87	74.42	70.90	73.16	61.88
0,1	bDGalp	104.20	70.73	78.29	66.18	74.22	68.12
0	xDRib-ol	71.93	72.08	72.98	72.38	67.87
	P

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize