Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Bacillus cereus [ICD11:
XN8PY 
]
The structure was elucidated in this paperNCBI PubMed ID: 21784857Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: yann.guerardel
univ-lille1.fr
Institutions: Universite de Lille1, Unite de Glycobiologie Structurale et Fonctionnelle, F-59650 Villeneuve d'Ascq, France
Bacterial species from the Bacillus genus, including Bacillus cereus and Bacillus anthracis, synthesize secondary cell wall polymers (SCWP) covalently associated to the peptidoglycan through a phospho-diester linkage. Although such components were observed in a wide panel of B. cereus and B. anthracis strains, the effect of culture conditions or of bacterial growth state on their synthesis has never been addressed. Herein we show that B. cereus ATCC 14579 can synthesize not only one, as previously reported, but two structurally unrelated secondary cell wall polymers (SCWP) polysaccharides. The first of these SCWP, →4)[GlcNAc(β1-3)]GlcNAc(β1-6)[Glc(β1-3)][ManNAc(α1-4)]GalNA c(α1-4)ManNAc(β1→, although presenting an original sequence, fits to the already described the canonical sequence motif of SCWP. In contrast, the second polysaccharide was made up by a totally original sequence, →6)Gal(α1-2)(2-R-hydroxyglutar-5-ylamido)Fuc2NAc4N(α1-6)GlcNAc(β1→, which no equivalent has ever been identified in the Bacillus genus. In addition, we established that the syntheses of these two polysaccharides were differently regulated. The first one is constantly expressed at the surface of the bacteria, whereas the expression of the second is tightly regulated by culture conditions and growth states, planktonic, or biofilm.
cell wall polysaccharide, Biofilm, Bacillus cereus
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.31259,fig.8 Ne HF-PS
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_149549,IEDB_151531,IEDB_423151,IEDB_885813,IEDB_885822,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, GC-MS, HF solvolysis, sugar analysis, TLC, 31P NMR, mild acid hydrolysis, MALDI-TOF MS, NMR-1D, HR-MAS NMR, MALDI-MS/MS
Comments, role: Neutral (Ne) HF release polysaccharide from planktonic phase.
Related record ID(s): 26574
NCBI Taxonomy refs (TaxIDs): 226900Reference(s) to other database(s): GTC:G37330XD
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,6,2 Ac ? 23.62
4,6,3,2 Ac ? 23.62
4,6,3 bDGlcpN 96.6 57.0 75.8 72.1 77.4 62.4
4,6 bDGlcpN 102.5 56.4 80.3 73.6 75.4 62.4
4,2 Ac ? 23.62
4,3 bDGlcp 105.9 74.3 76.0 71.4 75.4 62.4
4,4,2 Ac ? 23.62
4,4 aDManpN 98.04 55.20 71.64 70.72 72.62 62
4 aDGalpN 98.5 49.72 77.08 75.20 71.3 68.60
2 Ac ? 23.62
bDManpN 100.93 49.63 75.8 70.1 76.3 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,6,2 Ac - 2.125
4,6,3,2 Ac - 2.064
4,6,3 bDGlcpN 4.521 3.592 3.480 3.298 3.473 3.66-3.99
4,6 bDGlcpN 4.471 3.721 3.721 3.721 3.55 3.66-3.99
4,2 Ac - 2.092
4,3 bDGlcp 4.428 3.139 3.473 3.350 3.55 3.66-3.99
4,4,2 Ac - 1.999
4,4 aDManpN 5.021 3.915 3.911 3.610 4.323 3.7-3.9
4 aDGalpN 5.588 4.551 3.956 4.258 4.086 3.636-3.907
2 Ac - 2.092
bDManpN 4.897 4.740 4.538 3.855 3.570 3.66-3.99
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,6,2 Ac 23.62/2.125
4,6,3,2 Ac 23.62/2.064
4,6,3 bDGlcpN 96.6/4.521 57.0/3.592 75.8/3.480 72.1/3.298 77.4/3.473 62.4/3.66-3.99
4,6 bDGlcpN 102.5/4.471 56.4/3.721 80.3/3.721 73.6/3.721 75.4/3.55 62.4/3.66-3.99
4,2 Ac 23.62/2.092
4,3 bDGlcp 105.9/4.428 74.3/3.139 76.0/3.473 71.4/3.350 75.4/3.55 62.4/3.66-3.99
4,4,2 Ac 23.62/1.999
4,4 aDManpN 98.04/5.021 55.20/3.915 71.64/3.911 70.72/3.610 72.62/4.323 62/3.7-3.9
4 aDGalpN 98.5/5.588 49.72/4.551 77.08/3.956 75.20/4.258 71.3/4.086 68.60/3.636-3.907
2 Ac 23.62/2.092
bDManpN 100.93/4.897 49.63/4.740 75.8/4.538 70.1/3.855 76.3/3.570 62.4/3.66-3.99
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,6,2 | Ac |
| 2.125 | |
| 4,6,3,2 | Ac |
| 2.064 | |
| 4,6,3 | bDGlcpN | 4.521 | 3.592 | 3.480 | 3.298 | 3.473 | 3.66
3.99 |
| 4,6 | bDGlcpN | 4.471 | 3.721 | 3.721 | 3.721 | 3.55 | 3.66
3.99 |
| 4,2 | Ac |
| 2.092 | |
| 4,3 | bDGlcp | 4.428 | 3.139 | 3.473 | 3.350 | 3.55 | 3.66
3.99 |
| 4,4,2 | Ac |
| 1.999 | |
| 4,4 | aDManpN | 5.021 | 3.915 | 3.911 | 3.610 | 4.323 | 3.7
3.9 |
| 4 | aDGalpN | 5.588 | 4.551 | 3.956 | 4.258 | 4.086 | 3.636
3.907 |
| 2 | Ac |
| 2.092 | |
| | bDManpN | 4.897 | 4.740 | 4.538 | 3.855 | 3.570 | 3.66
3.99 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,6,2 | Ac | ? | 23.62 | |
| 4,6,3,2 | Ac | ? | 23.62 | |
| 4,6,3 | bDGlcpN | 96.6 | 57.0 | 75.8 | 72.1 | 77.4 | 62.4 |
| 4,6 | bDGlcpN | 102.5 | 56.4 | 80.3 | 73.6 | 75.4 | 62.4 |
| 4,2 | Ac | ? | 23.62 | |
| 4,3 | bDGlcp | 105.9 | 74.3 | 76.0 | 71.4 | 75.4 | 62.4 |
| 4,4,2 | Ac | ? | 23.62 | |
| 4,4 | aDManpN | 98.04 | 55.20 | 71.64 | 70.72 | 72.62 | 62 |
| 4 | aDGalpN | 98.5 | 49.72 | 77.08 | 75.20 | 71.3 | 68.60 |
| 2 | Ac | ? | 23.62 | |
| | bDManpN | 100.93 | 49.63 | 75.8 | 70.1 | 76.3 | 62.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":23.62,"l":"2","c":[0,0,0]},{"s":23.62,"l":"2","c":[0,0,0]},{"s":96.6,"l":"1","c":[0,0,225]},{"s":57,"l":"2","c":[0,0,225]},{"s":75.8,"l":"3","c":[0,0,225]},{"s":72.1,"l":"4","c":[0,0,225]},{"s":77.4,"l":"5","c":[0,0,225]},{"s":62.4,"l":"6","c":[0,0,225]},{"s":102.5,"l":"1","c":[230,0,30]},{"s":56.4,"l":"2","c":[230,0,30]},{"s":80.3,"l":"3","c":[230,0,30]},{"s":73.6,"l":"4","c":[230,0,30]},{"s":75.4,"l":"5","c":[230,0,30]},{"s":62.4,"l":"6","c":[230,0,30]},{"s":23.62,"l":"2","c":[0,0,0]},{"s":105.9,"l":"1","c":[0,165,0]},{"s":74.3,"l":"2","c":[0,165,0]},{"s":76,"l":"3","c":[0,165,0]},{"s":71.4,"l":"4","c":[0,165,0]},{"s":75.4,"l":"5","c":[0,165,0]},{"s":62.4,"l":"6","c":[0,165,0]},{"s":23.62,"l":"2","c":[0,0,0]},{"s":98.04,"l":"1","c":[120,0,225]},{"s":55.2,"l":"2","c":[120,0,225]},{"s":71.64,"l":"3","c":[120,0,225]},{"s":70.72,"l":"4","c":[120,0,225]},{"s":72.62,"l":"5","c":[120,0,225]},{"s":62,"l":"6","c":[120,0,225]},{"s":98.5,"l":"1","c":[0,192,255]},{"s":49.72,"l":"2","c":[0,192,255]},{"s":77.08,"l":"3","c":[0,192,255]},{"s":75.2,"l":"4","c":[0,192,255]},{"s":71.3,"l":"5","c":[0,192,255]},{"s":68.6,"l":"6","c":[0,192,255]},{"s":23.62,"l":"2","c":[0,0,0]},{"s":100.93,"l":"1","c":[220,0,180]},{"s":49.63,"l":"2","c":[220,0,180]},{"s":75.8,"l":"3","c":[220,0,180]},{"s":70.1,"l":"4","c":[220,0,180]},{"s":76.3,"l":"5","c":[220,0,180]},{"s":62.4,"l":"6","c":[220,0,180]}])
The spectrum also has 5 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
