Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Bacillus subtilis [ICD11:
XM4SG9 
]
The structure was elucidated in this paperNCBI PubMed ID: 24237149Publication DOI: 10.1134/S000629791310009XJournal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: potekhina56
mail.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, All-Russian Collection of Microorganisms, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, pr. Nauki 5, 142290, Pushchino, Moscow Region, Russia, fax: (495) 9394309
Disaccharide 1-phosphate polymers as well as teichoic acids of various structures have been found in the cell walls of the representatives of the Bacillus subtilis group, namely Bacillus subtilis subsp. spizizenii VKM B-720 and VKM B-916, B. subtilis VKM B-517, and Bacillus vallismortis VKM B-2653(T). Disaccharide 1-phosphate polymers are composed of repeating units of the following structure: -P-4)-β-D-GlcpNAc-(1→6)-α-D-Galp-(1-, the N-acetylglucosamine residues are partially acetylated at positions O3 and O6 (VKM B-720 and VKM B-916); -P-4)-β-D-Glcp-(1→6)-α-D-GlcpNAc-(1-, the glucopyranose residues are partially acetylated at positions O2 or O3 (VKM B-517); -P-6)-α-D-GlcpNH3(+)/α-D-GlcpNAc-(1→2)-α-D-Glcp-(1-, the N-acetylglucosamine residues are partially deacetylated (VKM B-2653(T)). The structures of the two last disaccharide 1-phosphate polymers have not been reported so far for Gram-positive bacteria. The teichoic acids in the studied strains are O-D-alanyl-1,5-poly(ribitol phosphates) substituted with β-D-glucopyranose (VKM B-517, VKM B-720, VKM B-916) or 2-acetamido-2-deoxy-β-D-glucopyranose (VKM B-2653(T)). The structures of the phosphate-containing polymers have been studied by chemical methods and by NMR spectroscopy.
NMR spectroscopy, teichoic acids, Bacillus subtilis, glycosyl 1-phosphate polymers, Bacillus subtilis subsp. spizizenii, Bacillus vallismortis
Structure type: oligomer
Location inside paper: table 1, polymer 2, disaccharide
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, acid hydrolysis, paper chromatography, NMR-1D, paper electrophoresis
Related record ID(s): 29323, 29728, 29729, 29730, 29731, 29732, 29733, 29734, 29735, 29737, 29738, 29740, 29741, 29742, 29743
NCBI Taxonomy refs (TaxIDs): 1423Reference(s) to other database(s): GTC:G82190PW
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6 bDGlcp 103.9 74.3 76.8 70.9 77.1 61.9
2 Ac 175.7 23.1-23.4
aDGlcpN 92.1 55.2 71.8 71.1 71.8 69.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6 bDGlcp 4.51 3.32 3.48 3.39 3.45 3.72-3.91
2 Ac - 2.05-2.06
aDGlcpN 5.19 3.87 3.76 3.57 4.01 3.90-4.16
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6 bDGlcp 103.9/4.51 74.3/3.32 76.8/3.48 70.9/3.39 77.1/3.45 61.9/3.72-3.91
2 Ac 23.1-23.4/2.05-2.06
aDGlcpN 92.1/5.19 55.2/3.87 71.8/3.76 71.1/3.57 71.8/4.01 69.8/3.90-4.16
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6 | bDGlcp | 4.51 | 3.32 | 3.48 | 3.39 | 3.45 | 3.72
3.91 |
| 2 | Ac |
| 2.05
2.06 | |
| | aDGlcpN | 5.19 | 3.87 | 3.76 | 3.57 | 4.01 | 3.90
4.16 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6 | bDGlcp | 103.9 | 74.3 | 76.8 | 70.9 | 77.1 | 61.9 |
| 2 | Ac | 175.7 | 23.1
23.4 | |
| | aDGlcpN | 92.1 | 55.2 | 71.8 | 71.1 | 71.8 | 69.8 |
|
There is only one chemically distinct structure:
Found 
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