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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: infection due to Bacillus subtilis [ICD11: XM4SG9

]

The structure was elucidated in this paper
NCBI PubMed ID: 21514573
Publication DOI: 10.1016/j.carres.2011.03.034
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: G.M. Streshinskaya <streshinskaya

mail.ru>
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation

The cell wall of Bacillus subtilis VKM B-762 contains, along with 1,5-poly[4-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)ribitol phosphate], a novel type of glycopolymer involving three types of inter-monomeric bonds in the repeating unit, viz., amide, glycosidic and phosphodiester: [See figure in text]. Such a structural pattern of natural glycopolymers has been hitherto unknown. This polymer represents a novel type of teichoic acids.

cell wall, teichoic acid, Bacillus, Bacillus subtilis, NMR-spectroscopy

Structure type: oligomer
Location inside paper: p. 1175, table 1, glycoside A
Contained glycoepitopes: IEDB_114703,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531

Methods: 13C NMR, 1H NMR, deacetylation, NMR-2D, partial acid hydrolysis, HF solvolysis, 31P NMR, ESI-MS, composition analysis, peracetylation

Related record ID(s): 26345, 26456, 26457, 26458, 26459
NCBI Taxonomy refs (TaxIDs): 1423
Reference(s) to other database(s): GTC:G99772HB
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,2	Ac	176.3	23.6
4	bDGlcpN	102.8	57.3	75.2	71.3	77.2	62.1
	x?Rib-ol	64.1	73.1	73.0	82.5	62.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,2	Ac	-	2.05
4	bDGlcpN	4.71	3.73	3.59	3.47	3.47	3.76-3.93
	x?Rib-ol	3.83	3.80	3.88	3.98	3.72-3.84


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4,2	Ac		23.6/2.05
4	bDGlcpN	102.8/4.71	57.3/3.73	75.2/3.59	71.3/3.47	77.2/3.47	62.1/3.76-3.93
	x?Rib-ol	64.1/3.83	73.1/3.80	73.0/3.88	82.5/3.98	62.0/3.72-3.84

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
4,2	Ac		2.05
4	bDGlcpN	4.71	3.73	3.59	3.47	3.47	3.76 3.93
	x?Rib-ol	3.83	3.80	3.88	3.98	3.72 3.84

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
4,2	Ac	176.3	23.6
4	bDGlcpN	102.8	57.3	75.2	71.3	77.2	62.1
	x?Rib-ol	64.1	73.1	73.0	82.5	62.0

There are 2 chemically distinct structures. Please, select:

CC(=O)N[C@H]1[C@H](O[C@H](CO)[C@@H](O)[C@@H](O)CO)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize