Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Bacillus subtilis [ICD11:
XM4SG9 
]
The structure was elucidated in this paperNCBI PubMed ID: 19961419Publication DOI: 10.1134/S0006297909120116Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: potekchina
hotbox.ru
Institutions: Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia
Cell walls of Bacillus subtilis VKM B-760 and VKM B-764 are characterized by heterogeneous composition of teichoic acids. Polymer I with structure -6)-β-D-Galp-(1→1)-sn-Gro-(3-P-, polymer II with structure -6)-α-D-Glcp-(1→1)-sn-Gro-(3-P-, and a small amount of unsubstituted 1,3-poly(glycerol phosphate) were detected in strain VKM B-760. Strain VKM B-764 contains an analogous set of teichoic acids, but a characteristic feature of polymer II is the presence of disubstituted glycerol residue with α-glucopyranose localization in the integral chain at C-1 hydroxyl and β-glucopyranose as a side branch at C-2 hydroxyl (polymer III): -6)-α-D-Glcp-(1→1)-[β-D-Glcp-(1→2)]-sn-Gro-(3-P-. The structures of polymer I in bacilli and polymer III in Gram-positive bacteria are described for the first time. Teichoic acids were studied by chemical methods and on the basis of combined analysis of one-dimensional 1H-, 13C-, and (31)P-NMR spectra, homonuclear two-dimensional (1)H/(1)H COSY, TOCSY, and ROESY, and heteronuclear two-dimensional (1)H/(13)C gHSQC- and HMQC-TOCSY experiments. Simultaneous presence of several different structure teichoic acids in the bacillus cell walls as well as chemotaxonomical perspectives of the application of these polymers as species-specific markers for members of the Bacillus genus is discussed.
NMR spectroscopy, cell wall, teichoic acids, Bacillus subtilis
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.1371, polymer I
Trivial name: teichoic acid
Compound class: cell wall polysaccharide, teichoic acid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_241118,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, NMR-1D, genetic methods, acid degradation
Biosynthesis and genetic data: genetic data
Related record ID(s): 23819, 24185, 24186, 24187, 24188
NCBI Taxonomy refs (TaxIDs): 1423Reference(s) to other database(s): GTC:G37566GP
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
0,1 aDGlcp 99.9 72.9 74.4 70.5 72.2 65.8
0 x?Gro 69.7 70.5 68.1
P
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
0,1 aDGlcp 4.93 3.58 3.76 3.53 3.79 4.04-4.15
0 x?Gro 3.63-3.83 4.10 3.98-4.01
P
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
0,1 aDGlcp 99.9/4.93 72.9/3.58 74.4/3.76 70.5/3.53 72.2/3.79 65.8/4.04-4.15
0 x?Gro 69.7/3.63-3.83 70.5/4.10 68.1/3.98-4.01
P
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 0,1 | aDGlcp | 4.93 | 3.58 | 3.76 | 3.53 | 3.79 | 4.04
4.15 |
| 0 | x?Gro | 3.63
3.83 | 4.10 | 3.98
4.01 | |
| | P | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 0,1 | aDGlcp | 99.9 | 72.9 | 74.4 | 70.5 | 72.2 | 65.8 |
| 0 | x?Gro | 69.7 | 70.5 | 68.1 | |
| | P | |
|
There is only one chemically distinct structure:
Found 
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