Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
Publication DOI: 10.1016/0040-4039(95)01433-0Journal NLM ID: 2984819RPublisher: Elsevier
Institutions: Department of Chemistry, Faculty of Science, Osaka University, Toyonaka, Osaka 560, Japan, Forschungsinstitut Borstel, Parkallee 22, 23845, Borstel, Germany
Synthesis of an analog of a biosynthetic precursor of lipid A containing four (S)-3-hydroxytetradecanoic acids was effected via an improved synthetic route to investigate the relationship between the bioactivity and the chirality of the 3-hydroxy fatty acid residues in lipid A. The S-analog inhibited endotoxin-induced interleukin-6 (IL-6) production from human peripheral whole blood cells more strongly than the natural-type biosynthetic precursor with (R)-hydroxy acids, a known antagonist of LPS-induced cytokine release in human peripheral blood mononuclear cells.
synthesis, biosynthetic, lipid A, precursor, antagonist, fatty acid, fatty acids, method
Structure type: oligomer
Location inside paper: p.7455, fig.1, E. coli lipid A, 1
Compound class: LPS, lipid A, glycolipid, phosphoglycolipid
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864
Methods: FAB-MS, NMR, TLC, chemical synthesis, chemical methods
Biological activity: cytokine induction activity
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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