Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: pneumonia [ICD11:
CA40 
];
bacteremia [ICD11:
MA15.0 ];
meningitis [ICD11:
1D01 ];
infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
The structure was elucidated in this paperNCBI PubMed ID: 20878800Publisher: Vch Verlagsgesellschaft
Correspondence: richard.schmidt
uni-konstanz.de
Institutions: Fachbereich Chemie, Universitat Konstanz, Fach 725, 78457 Konstanz, Germany
Streptococcus pneumoniae LTA is a highly complex glycophospholipid that consists of nine carbohydrate residues: three glucose, two galactosamine and two 2-acetamino-4-amino-2,4,6-trideoxygalactose (AATDgal) residues that are each differently linked, one ribitol and one diacylated glycerol (DAG) residue. Suitable building blocks for the glucose and the AATDgal residues were designed and their synthesis is described in this paper. These building blocks permitted the successful synthesis of the core structure Glcβ(1-3)AATDgalβ(1-3)Glcα(1-O)DAG in a suitably protected form for further chain extension (1 b, 1 c) and as unprotected glycolipid (1 a) that was employed in biological studies. These studies revealed that 1 a as well as 1 lead to interleukin-8 release, however not via TLR2 or TLR4 as receptor.
synthesis, carbohydrates, Streptococcus pneumoniae, glycolipids, glycosidation, receptor recognition, total synthesis
Structure type: oligomer
Location inside paper: p.12628, scheme 1 and 1a
Trivial name: glycolipidic core
Contained glycoepitopes: IEDB_142345,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_176772,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, ESI-ICR-MS, chemical synthesis
Biological activity: the induction of innate immune responces
Synthetic data: chemical
Comments, role: rightmost part of the LTA structure (leftmost part see ID: 25382)
Related record ID(s): 25382
NCBI Taxonomy refs (TaxIDs): 1313
Show glycosyltransferases
NMR conditions: in CD3OD at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,2 lXMyr
1,3,4,3 bDGlcp 101.3 75.6 78.8 72.1 72.3 63.5
1,3,4,2 Ac ? 24.92
1,3,4 bDFucpN4N 106.6 55.8 63.3 50.5 70.3 22.5
1,3 aDGlcp 102.2 73.3 70.6 78.3 74.2 63.2
1 xDGro 64.5 73.6 67.9
lXMyr
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,2 lXMyr
1,3,4,3 bDGlcp 4.820 3.241 3.28 3.28 3.678 3.63-3.67
1,3,4,2 Ac - 2.04
1,3,4 bDFucpN4N 4.387 3.219 3.83 3.378 4.00 1.32
1,3 aDGlcp 4.816 3.529 3.390 3.352 3.61 3.69-3.71
1 xDGro 4.241-4.497 5.290 3.68-3.903
lXMyr
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,2 lXMyr
1,3,4,3 bDGlcp 101.3/4.820 75.6/3.241 78.8/3.28 72.1/3.28 72.3/3.678 63.5/3.63-3.67
1,3,4,2 Ac 24.92/2.04
1,3,4 bDFucpN4N 106.6/4.387 55.8/3.219 63.3/3.83 50.5/3.378 70.3/4.00 22.5/1.32
1,3 aDGlcp 102.2/4.816 73.3/3.529 70.6/3.390 78.3/3.352 74.2/3.61 63.2/3.69-3.71
1 xDGro 64.5/4.241-4.497 73.6/5.290 67.9/3.68-3.903
lXMyr
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,2 | lXMyr | |
| 1,3,4,3 | bDGlcp | 4.820 | 3.241 | 3.28 | 3.28 | 3.678 | 3.63
3.67 |
| 1,3,4,2 | Ac |
| 2.04 | |
| 1,3,4 | bDFucpN4N | 4.387 | 3.219 | 3.83 | 3.378 | 4.00 | 1.32 |
| 1,3 | aDGlcp | 4.816 | 3.529 | 3.390 | 3.352 | 3.61 | 3.69
3.71 |
| 1 | xDGro | 4.241
4.497 | 5.290 | 3.68
3.903 | |
| | lXMyr | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,2 | lXMyr | |
| 1,3,4,3 | bDGlcp | 101.3 | 75.6 | 78.8 | 72.1 | 72.3 | 63.5 |
| 1,3,4,2 | Ac | ? | 24.92 | |
| 1,3,4 | bDFucpN4N | 106.6 | 55.8 | 63.3 | 50.5 | 70.3 | 22.5 |
| 1,3 | aDGlcp | 102.2 | 73.3 | 70.6 | 78.3 | 74.2 | 63.2 |
| 1 | xDGro | 64.5 | 73.6 | 67.9 | |
| | lXMyr | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":101.3,"l":"1","c":[230,0,30]},{"s":75.6,"l":"2","c":[230,0,30]},{"s":78.8,"l":"3","c":[230,0,30]},{"s":72.1,"l":"4","c":[230,0,30]},{"s":72.3,"l":"5","c":[230,0,30]},{"s":63.5,"l":"6","c":[230,0,30]},{"s":24.92,"l":"2","c":[0,0,0]},{"s":106.6,"l":"1","c":[0,165,0]},{"s":55.8,"l":"2","c":[0,165,0]},{"s":63.3,"l":"3","c":[0,165,0]},{"s":50.5,"l":"4","c":[0,165,0]},{"s":70.3,"l":"5","c":[0,165,0]},{"s":22.5,"l":"6","c":[0,165,0]},{"s":102.2,"l":"1","c":[120,0,225]},{"s":73.3,"l":"2","c":[120,0,225]},{"s":70.6,"l":"3","c":[120,0,225]},{"s":78.3,"l":"4","c":[120,0,225]},{"s":74.2,"l":"5","c":[120,0,225]},{"s":63.2,"l":"6","c":[120,0,225]},{"s":64.5,"l":"1","c":[0,192,255]},{"s":73.6,"l":"2","c":[0,192,255]},{"s":67.9,"l":"3","c":[0,192,255]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
