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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
Publication DOI: 10.1134/S0026261711010164
Journal NLM ID: 0376652
Publisher: Moskva: Izdatelstvo Nauka
Correspondence: streshinskaya

mail.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia, All-Russian Collection of Microorganisms, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Institute of Ecology and Genetics of Microorganisms, Ural Division Russian Academy of Sciences Perm Russia

A comparative study of the structures of carbohydrate-containing cell wall polymers isolated from the strains of the Bacillus subtilis group was performed by means of chemical and NMR spectroscopic meth ods. Polymers of different structure were revealed, namely, 1,3-poly(glycerol phosphates) with β-glucopyranose in Bacillus subtilis strains VKM B-520, VKM B-723, and VKM B-763 (= VKM B-911); 1,5-poly(ribitol phosphate) with α-glucopyranose in B. subtilis strains VKM B-722 and VKM B-922 (the structure is reported for the first time); and simultaneously two polymers in B. subtilis VKM B-761, 1,5-poly(ribitol phosphate) with β-glucopyranose and the disaccharide 1-phosphate polymer with the following repeating unit: -6)-α-D-Galp-(1-P-4)-gB-D-GlcpNAc-(1-, in which the hydroxyls at C3 and C6 of glucosamine residues are partially O-acetylated (the structure is reported for the first time). Heterogeneity of the B. subtilis group is con firmed by variations in the structure and composition of the cell wall polymers. The cell surface polymers are useful for discrimination of closely related bacilli strains and are cell wall marker components that may be an indispensable element of the Bacillus subtilis group taxonomy along with the genomosystematic methods.

NMR spectroscopy, cell wall, teichoic acid, Bacillus subtilis, taxonomy, disaccharide 1-phosphate polymer

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.24, table 4(polymer), p.28, table 5
Trivial name: teichoic acid, cell wall disaccharide 1-phosphate polymer
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_7

Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, paper chromatography, NMR-1D, electrophoresis, RNA sequencing

Related record ID(s): 26355, 26476, 26477, 26478, 26479, 26480, 26482, 26483, 26484, 26485, 26486, 26487, 26488, 26489, 26490, 26491, 26492
NCBI Taxonomy refs (TaxIDs): 1423
Reference(s) to other database(s): GTC:G67129GK
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,6,2	Ac	176.8	23.5
0,6,3	40%Ac	174.8	21.8
0,6,6	60%Ac	174.8	21.8
0,6	bDGlcpN	101.7	55.3	75.9	73.2	73.9	64.6
0	aDGalp	97.2	69.7	70.6	70.2	71.3	68.6
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,6,2	Ac	-	2.01
0,6,3	40%Ac	-	2.15
0,6,6	60%Ac	-	2.12
0,6	bDGlcpN	4.89	3.90	5.17	4.37	3.81	4.40-4.52
0	aDGalp	5.46	3.82	3.82	3.97	4.11	3.81-3.93
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,6,2	Ac		23.5/2.01
0,6,3	40%Ac		21.8/2.15
0,6,6	60%Ac		21.8/2.12
0,6	bDGlcpN	101.7/4.89	55.3/3.90	75.9/5.17	73.2/4.37	73.9/3.81	64.6/4.40-4.52
0	aDGalp	97.2/5.46	69.7/3.82	70.6/3.82	70.2/3.97	71.3/4.11	68.6/3.81-3.93
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,6,2	Ac		2.01
0,6,3	40%Ac		2.15
0,6,6	60%Ac		2.12
0,6	bDGlcpN	4.89	3.90	5.17	4.37	3.81	4.40 4.52
0	aDGalp	5.46	3.82	3.82	3.97	4.11	3.81 3.93
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,6,2	Ac	176.8	23.5
0,6,3	40%Ac	174.8	21.8
0,6,6	60%Ac	174.8	21.8
0,6	bDGlcpN	101.7	55.3	75.9	73.2	73.9	64.6
0	aDGalp	97.2	69.7	70.6	70.2	71.3	68.6
	P

There is only one chemically distinct structure:

*O[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC[C@H]2O[C@H](OP(*)(=O)O)[C@H](O)[C@@H](O)[C@H]2O)[C@H](NC(C)=O)[C@H]1OC(C)=O

SVG MW SMILES 3D mol Ionize