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Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida.

Publication ,  Journal Article
Wang, X; Ribeiro, AA; Guan, Z; McGrath, SC; Cotter, RJ; Raetz, CRH
Published in: Biochemistry
December 5, 2006

Francisella tularensis subsp. novicida U112 phospholipids, extracted without hydrolysis, consist mainly of phosphatidylethanolamine, phosphatidylglycerol, phosphatidylcholine, and two lipid A species, designated A1 and A2. These lipid A species, present in a ratio of 7:1, comprise 15% of the total phospholipids, as judged by 32Pi labeling. Although lipopolysaccharide is detectable in F. tularensis subsp. novicida U112, less than 5% of the total lipid A is covalently linked to it. A1 and A2 were analyzed by electrospray ionization and matrix-assisted laser desorption ionization mass spectrometry, gas chromatography/mass spectrometry, and NMR spectroscopy. Both compounds are disaccharides of glucosamine, acylated with primary 3-hydroxystearoyl chains at positions 2, 3, and 2' and a secondary palmitoyl residue at position 2'. Minor isobaric species and some lipid A molecules containing a 3-hydroxypalmitoyl chain in place of 3-hydroxystearate are also present. The 4'- and 3'-positions of A1 and A2 are not derivatized, and 3-deoxy-d-manno-octulosonic acid (Kdo) is not detectable. The 1-phosphate groups of both A1 and A2 are modified with an alpha-linked galactosamine residue, as shown by NMR spectroscopy and gas chromatography/mass spectrometry. An alpha-linked glucose moiety is attached to the 6'-position of A2. The lipid A released by mild acid hydrolysis of F. tularensis subsp. novicida lipopolysaccharide consists solely of component A1. F. tularensis subsp. novicida mutants lacking the arnT gene do not contain a galactosamine residue on their lipid A. Formation of free lipid A in F. tularensis subsp. novicida might be initiated by an unusual Kdo hydrolase present in the membranes of this organism.

Duke Scholars

Published In

Biochemistry

DOI

ISSN

0006-2960

Publication Date

December 5, 2006

Volume

45

Issue

48

Start / End Page

14427 / 14440

Location

United States

Related Subject Headings

  • Phospholipids
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Lipid A
  • Ions
  • Hydrolysis
  • Galactosamine
  • Francisella tularensis
  • Carbohydrate Conformation
  • Biochemistry & Molecular Biology
 

Citation

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Wang, X., Ribeiro, A. A., Guan, Z., McGrath, S. C., Cotter, R. J., & Raetz, C. R. H. (2006). Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida. Biochemistry, 45(48), 14427–14440. https://doi.org/10.1021/bi061767s
Wang, Xiaoyuan, Anthony A. Ribeiro, Ziqiang Guan, Sara C. McGrath, Robert J. Cotter, and Christian R. H. Raetz. “Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida.Biochemistry 45, no. 48 (December 5, 2006): 14427–40. https://doi.org/10.1021/bi061767s.
Wang X, Ribeiro AA, Guan Z, McGrath SC, Cotter RJ, Raetz CRH. Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida. Biochemistry. 2006 Dec 5;45(48):14427–40.
Wang, Xiaoyuan, et al. “Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida.Biochemistry, vol. 45, no. 48, Dec. 2006, pp. 14427–40. Pubmed, doi:10.1021/bi061767s.
Wang X, Ribeiro AA, Guan Z, McGrath SC, Cotter RJ, Raetz CRH. Structure and biosynthesis of free lipid A molecules that replace lipopolysaccharide in Francisella tularensis subsp. novicida. Biochemistry. 2006 Dec 5;45(48):14427–14440.
Journal cover image

Published In

Biochemistry

DOI

ISSN

0006-2960

Publication Date

December 5, 2006

Volume

45

Issue

48

Start / End Page

14427 / 14440

Location

United States

Related Subject Headings

  • Phospholipids
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Lipid A
  • Ions
  • Hydrolysis
  • Galactosamine
  • Francisella tularensis
  • Carbohydrate Conformation
  • Biochemistry & Molecular Biology