Structural characterization of the lipid A component of pathogenic Neisseria meningitidis.
The lipid A component of meningococcal lipopolysaccharide was structurally characterized by using chemical modification methods, methylation analysis, 31P nuclear magnetic resonance, and laser desorption mass spectroscopy. It was shown that Neisseria meningitidis lipid A consists of a 1,4'-bisphosphorylated beta(1'----6)-linked D-glucosamine disaccharide (lipid A backbone), both phosphate groups being largely replaced by O-phosphorylethanolamine. This disaccharide harbors two nonsubstituted hydroxyl groups at positions 4 and 6', the latter representing the attachment site of the oligosaccharide portion in lipopolysaccharide. In addition, it is substituted by up to six fatty acid residues. In the major lipid A component, representing a hexaacyl species, the hydroxyl groups at positions 3 and 3' carry (R)-3-hydroxydodecanoic acid [12:0(3-OH)], whereas the amino groups at positions 2 and 2' are substituted by (R)-3-(dodecanoyloxy)tetradecanoic acid [3-O(12:0)-14:0]. A minor portion was present as a tetraacyl lipid A component lacking either dodecanoic acid (12:0) or 12:0 and 12:0(3-OH). N. meningitidis lipid A, therefore, significantly differs from Escherichia coli lipid A by the nature and locations of fatty acids and the substitution of O-phosphorylethanolamine for the nonglycosyl (4'-P) and glycosyl phosphate.
Kulshin
V A
VA
Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Germany.
Zähringer
U
U
Lindner
B
B
Frasch
C E
CE
Tsai
C M
CM
Dmitriev
B A
BA
Rietschel
E T
ET
D005227:Fatty Acids / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D008050:Lipid A / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009345:Neisseria meningitidis / Q000737:chemistry* / Q000472:pathogenicity; D009844:Oligosaccharides / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry
D005227:Fatty Acids; D008050:Lipid A; D009844:Oligosaccharides; D010710:Phosphates