Journal
EUROPEAN JOURNAL OF BIOCHEMISTRY
Volume 269, Issue 24, Pages 6112-6118Publisher
BLACKWELL PUBLISHING LTD
DOI: 10.1046/j.1432-1033.2002.03321.x
Keywords
Francisella tularensis; lipopolysaccharide; core; lipid A
Categories
Funding
- NIAID NIH HHS [R01 AI048474-05, R01 AI048474, AI48474] Funding Source: Medline
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The structure of the lipid A and core region of the lipopolysaccharide (LPS) from Francisella tularensis (ATCC 29684) was analysed using NMR, mass spectrometry and chemical methods. The LPS contains a beta-GlcN-(1-6)-GlcN lipid A backbone, but has a number of unusual structural features; it apparently has no substituent at O-1 of the reducing end GlcN residue in the lipid part in the major part of the population, no substituents at O-3 and O-4 of beta-GlcN, and no substituent at O-4 of the Kdo residue. The largest oligosaccharide, isolated after strong alkaline deacylation of NaBH4 reduced LPS had the following structure: [GRAPHICS] where Delta-GalNA-(1-3)-beta-QuiNAc represents a modified fragment of the O-chain repeating unit. Two shorter oligosaccharides lacking the O-chain fragment were also identified. A minor amount of the disaccharide beta-GlcN-(1-6)-alpha-GlcN-1-P was isolated from the same reaction mixture, indicating the presence of free lipid A, unsubstituted by Kdo and with phosphate at the reducing end. The lipid A, isolated from the products of mild acid hydrolysis, had the structure 2-N -(3-O-acyl(4) -acyl(2) )-beta-GlcN-(1-6)-2-N -acyl(1) -3-O-acyl(3) -GlcN where acyl(1) , acyl(2) and acyl(3) are 3-hydroxyhexadecanoic or 3-hydroxyoctadecanoic acids, acyl(4) is tetradecanoic or (minor) hexadecanoic acids. No phosphate substituents were found in this compound. OH-1 of the reducing end glucosamine, and OH-3 and OH-4 of the nonreducing end glucosamine residues were not substituted. LPS of F. tularensis exhibits unusual biological properties, including low endoxicity, which may be related to its unusual lipid A structure.
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