27-Hydroxyoctacosanoic acid is a major structural fatty acyl component of the lipopolysaccharide of Rhizobium trifolii ANU 843.
A new hydroxylated, very long-chain fatty acid has been isolated and characterized from the lipopolysaccharide (LPS) of Rhizobium trifolii ANU 843. The lipid A of the organism was degraded by mild alkali and borohydride and the products methylated, peracetylated, and fractionated on a C18 reverse-phase column. The major lipid fraction was reduced with lithium triethylborohydride, methylated, peracetylated, and subjected to thin layer chromatography. The methylated peracetylated acid and the reduced diacetylated diol (1,27-dihydroxyoctacosane diacetate) were isolated and characterized by mass spectrometry and 1H NMR spectroscopy using homonuclear decoupling. The identity and linkage of the new fatty acid in the lipopolysaccharide was confirmed by 1H NMR spectroscopy of purified lipid A fractions and similar NMR studies of lipid A after acylation by phenylisocyanate. In the native LPS, the 27-hydroxy C-28 fatty acid is acylated at the 27-hydroxy position by other 3-hydroxy fatty acids. About 50% of the total fatty acid content of the LPS of R. trifolii ANU 843 is 27-hydroxyoctacosanoic acid. This oxyacyloxy structure involving 27-hydroxyoctacosanoic appears to be the major structural feature of the lipid A of this organism.
Hollingsworth
R I
RI
Department of Biochemistry, Michigan State University, East Lansing 48824-1319.
Carlson
R W
RW
D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D003485:Cyanates; D006880:Hydroxy Acids / Q000032:analysis / Q000302:isolation & purification*; D017953:Isocyanates; D008050:Lipid A / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008823:Micelles; D015394:Molecular Structure; D012231:Rhizobium / Q000032:analysis*
D003485:Cyanates; D006880:Hydroxy Acids; D017953:Isocyanates; D008050:Lipid A; D008823:Micelles; C059845:27-hydroxyoctacosanoic acid; C025319:phenyl isocyanate