Preparation of a lipid a derivative that contains a 27-hydroxyoctacosanoic acid moiety.
[structure: see text] A general synthetic strategy for long-chain omega-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between omega-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for the preparation of lipid A derivatives of Rhizobium sin-1, which have the ability to inhibit the E. coli LPS-dependent synthesis of tumor necrosis factor by human monocytes.
Santhanam
Balaji
B
Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Road, Athens, Georgia 30602, USA.
Boons
Geert-Jan
GJ
D004926:Escherichia coli / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009000:Monocytes / Q000378:metabolism; D012231:Rhizobium / Q000737:chemistry / Q000378:metabolism; D000079424:Tumor Necrosis Factor Inhibitors
D006880:Hydroxy Acids; D008050:Lipid A; D008070:Lipopolysaccharides; D000079424:Tumor Necrosis Factor Inhibitors; C059845:27-hydroxyoctacosanoic acid