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 ]
NCBI 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: polymer chemical repeating unit ; n=1-8
Location inside paper: p.12628, scheme 1, 1
Aglycon: (1->6)glycolipidic core (ID 25382)
Trivial name: lipoteichoic acid (LTA)
Contained glycoepitopes: IEDB_114703,IEDB_115009,IEDB_116046,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_140624,IEDB_141109,IEDB_141582,IEDB_141584,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_241118,IEDB_885822,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: leftmost part of the LTA structure (rightmost part see ID: 25798)
Related record ID(s): 25798
NCBI Taxonomy refs (TaxIDs): 1313
Show glycosyltransferases
There is only one chemically distinct structure:
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