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Synthesis of the Core Structure of the Lipoteichoic Acid of Streptococcus pneumoniae
Author(s) -
Pedersen Christian Marcus,
FigueroaPerez Ignacio,
Boruwa Joshodeep,
Lindner Buko,
Ulmer Artur J.,
Zähringer Ulrich,
Schmidt Richard R.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001204
Subject(s) - lipoteichoic acid , residue (chemistry) , streptococcus pneumoniae , chemistry , glycolipid , biochemistry , stereochemistry , bacteria , biology , antibiotics , staphylococcus aureus , genetics
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.