Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Salmonella enterica [ICD11:
XN5VC 
]
NCBI PubMed ID: 10579826Journal NLM ID: 9716531Publisher: Washington, DC: American Chemical Society
Correspondence: dajohn
corixa.com
Institutions: Pharmaceutical Discovery Division, Ribi ImmunoChem Research, Inc., 553 Old Corvallis Road, Hamilton, Montana 59840, USA
The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLA) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toxoid vaccines, certain MLA derivatives enhance the production of tetanus toxoid-specific antibodies in mice.
synthesis, lipid, lipid A, activity, monophosphoryl lipid A, immunostimulants
Structure type: oligomer
Location inside paper: p.4640, compound 1
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, ELISA, chemical synthesis, chemical methods, biological assays, serological methods, HPLC, UV
Biological activity: biological activity data, induction of proinflammatory cytokines (TNF-α and IL-1β) in human peripheral monocytes
Related record ID(s): 31398
NCBI Taxonomy refs (TaxIDs): 70803
Show glycosyltransferases
There is only one chemically distinct structure:
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(later renamed to: Salmonella enterica ssp. enterica sv. Minnesota R595)