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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: polymer chemical repeating unit
Location inside paper: p. 1175, table 1, p.1176, polymer A
Trivial name: poly(glycosyl 1-phosphate)
Compound class: cell wall polysaccharide, teichoic acid
Contained glycoepitopes: IEDB_114703,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_591403,IEDB_841282

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

Related record ID(s): 26455, 26456, 26457, 26458, 26459
NCBI Taxonomy refs (TaxIDs): 1423
Reference(s) to other database(s): GTC:G26626ZE
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,4,2	Ac	176.4	23.9
0,4	bDGlcpN	102.8	57.2	75.4	71.3	77.3	62.6
0	x?Rib-ol	68.2	72.4	72.5	81.0	66.4
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,4,2	Ac	-	2.09
0,4	bDGlcpN	4.77	3.78	3.59	3.49	3.59	3.79-3.95
0	x?Rib-ol	4.02-4.11	4.00	3.94	4.17	4.00-4.17
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,4,2	Ac		23.9/2.09
0,4	bDGlcpN	102.8/4.77	57.2/3.78	75.4/3.59	71.3/3.49	77.3/3.59	62.6/3.79-3.95
0	x?Rib-ol	68.2/4.02-4.11	72.4/4.00	72.5/3.94	81.0/4.17	66.4/4.00-4.17
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,4,2	Ac		2.09
0,4	bDGlcpN	4.77	3.78	3.59	3.49	3.59	3.79 3.95
0	x?Rib-ol	4.02 4.11	4.00	3.94	4.17	4.00 4.17
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,4,2	Ac	176.4	23.9
0,4	bDGlcpN	102.8	57.2	75.4	71.3	77.3	62.6
0	x?Rib-ol	68.2	72.4	72.5	81.0	66.4
	P

There are 2 chemically distinct structures. Please, select:

*OC[C@H](O)[C@H](O)[C@@H](COP(*)(=O)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize