title: Synthesis of the core structure of the lipoteichoic acid of Streptococcus pneumoniae.
abstract: 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.
authors.affiliation: Fachbereich Chemie, Universität Konstanz, Fach 725, 78457 Konstanz, Germany.
authors.forename: Christian Marcus
authors.initials: CM
authors.lastname: Pedersen
authors.forename: Ignacio
authors.initials: I
authors.lastname: Figueroa-Perez
authors.forename: Joshodeep
authors.initials: J
authors.lastname: Boruwa
authors.forename: Buko
authors.initials: B
authors.lastname: Lindner
authors.forename: Artur J
authors.initials: AJ
authors.lastname: Ulmer
authors.forename: Ulrich
authors.initials: U
authors.lastname: Zähringer
authors.forename: Richard R
authors.initials: RR
authors.lastname: Schmidt
mesh_terms: D006017:Glycolipids / Q000737:chemistry; D057809:HEK293 Cells; D006801:Humans; D016209:Interleukin-8 / Q000097:blood / Q000187:drug effects; D008070:Lipopolysaccharides / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D013296:Streptococcus pneumoniae / Q000737:chemistry / Q000276:immunology*; D013682:Teichoic Acids / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D051195:Toll-Like Receptor 2 / Q000378:metabolism; D051197:Toll-Like Receptor 4 / Q000378:metabolism
chemical_list: D006017:Glycolipids; D016209:Interleukin-8; D008070:Lipopolysaccharides; D013682:Teichoic Acids; D051195:Toll-Like Receptor 2; D051197:Toll-Like Receptor 4; C009900:lipoteichoic acid