New synthesis and conformational analysis of lipid A: Biological activity and supramolecular assembly

Journal of Endotoxin Research

Volumn 5, Issue 1-2, 1999, Pages 46-51

  Fukase, Koichi ^a   Oikawa, Masato ^a   Suda, Yasuo ^a   Liu, Wen Chi ^a   Fukase, Yoshiyuki ^a   Shintaku, Tetsuya ^a   Sekljic, Harald ^a   Yoshizaki, Hiroaki ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIPID A; MEMBRANE LIPID;

BACTERIAL MEMBRANE; CONFERENCE PAPER; CONTROLLED STUDY; DRUG CONFORMATION; HYDROPHILICITY; ISOTOPE LABELING; LIPOGENESIS; MICELLE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT;

BACTERIA (MICROORGANISMS);

EID: 0032793077     PISSN: 09680519     EISSN: None     Source Type: Journal    
DOI: 10.1177/09680519990050012001     Document Type: Conference Paper

References (24)

1. Imoto M, Yoshimura H, Yamamoto M, Shimamoto T, Kusumoto S, Shiba T. Chemical synthesis of phosphorylated teraacyl disaccharide corresponding to a biosynthetic precursor of lipid A. Tetrahedron Lett 1984; 25: 2667.
2. Imoto M, Yoshimura H, Yamamoto M, Shimamoto T, Kusumoto S, Shiba T. Chemical synthesis of a biosynthetic precursor of Lipid A with a phosphoylated tetraacyl disaccharide structure. Bull Chem Soc Jpn 1987; 60: 2197.
3. Imoto M, Yoshimura H, Yamamoto M, Sakaguchi N, Kusumoto S, Shiba T. Total synthesis of Escherichia coli Lipid A. Tetrahedron Lett 1985; 26: 1545.
4. Imoto M, Yoshimura H, Shimamoto T, Sakaguchi N, Kusumoto S, Shiba T. Total synthesis of Escherichia coli Lipid A, the endotoxically active principle of cell-surface lipopolysaccharide. Bull Chem Soc Jpn 1987; 60: 2205.
5. Fukase K, Liu W-C, Suda Y et al. Synthesis of an analog of biosynthetic precursor 1a of lipid A by an improved method: A novel antagonist containing four (S)-3-hydroxy fatty acids. Tetrahedron Lett 1995; 41: 7455.
6. Liu W-C, Oikawa M, Fukase K et al. Enzymatic preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogues of lipid A containing the (S)-acid. Bull Chem Soc Jpn 1997; 70: 1441.
7. Oikawa M, Wada A, Yoshizaki H, Fukase K, Kusumoto S. New efficient synthesis of a biosynthetic precursor of Lipid A. Bull Chem Soc Jpn 1997; 70: 1435.
8. Fukase K, Fukase Y, Oikawa M, Liu W-C, Suda Y, Kusumoto S. Divergent synthesis and biological activities of lipid A analogues of shorter acyl chains. Tetrahedron 1998; 54: 4033.
9. 2. Synlett 1996; 1179.
10. Brade L, Holst O, Brade H. An artificial glycoconjugate containing the bisphosphorylated glucosamine disaccharide backbone of lipid A binds lipid A monoclonal antibodies. Infect Immun 1993; 61: 4514.
11. Ulmer AJ, Heine H, Feist W et al. Biological activity of synthetic phosphonooxyethyl analogs of lipid A and lipid A partial structures. Infect Immun 1992; 60: 3309
12. Kusama T, Soga T, Shioya E et al. Synthesis and antitumor activity of lipid A analogs having a phosphonooxyethyl group with α- or β-configuration at position 1. Chem Pharm Bull 1990; 38: 3366.
13. Kusama T, Soga T, Ono Y et al. Synthesis and biological activities of lipid A analogs: modification of a glycosidically bound group with chemically stable polar acidic groups and lipophilic groups on the disaccharide backbone with tetradecanoylglycyl groups. Chem Pharm Bull 1991; 39: 3244.
14. Liu W-C, Oikawa M, Fukase K, Suda Y, Kusumoto S. A divergent synthesis of lipid A and its chemically stable unnatural analogues. Bull Chem Soc Jpn 1999; 72: In press.
15. Fukase K, Fukase Y, Liu W-C, Hashimoto M, Suda Y, Oikawa M, Kusumoto S. Divergent synthesis and biological activities of lipid A analogues. 39th Symposium on the Chemistry of Natural Products, Sapporo (Japan), August 1997, Abstr. No. 67, p397.
16. 3H-labeled analogue of lipid A. Synlett 1996; 252.
17. Fukase K, Kirikae T, Liu W-C, Oikawa M, Kurosawa M, Suda Y, Kusumoto S. Submitted
18. 13C-labeled biosynthetic precursor of lipid A and its analogue with shorter acyl chains. Bull Chem Soc Jpn 1999; 72: in press.
19. Brandenburg K, Kusumoto S, Seydel U. Conformational studies of synthetic lipid A analogues and partial structures by infrared spectroscopy. Biochim Biophys Acta 1997; 183: 1329, and references therein.
20. Labischinski H, Barnickel G, Bradaczek H, Naumann D, Rietschel ETh, Giesbrecht P. High-state of order of isolated bacterial lipopolysaccharide and its possible contribution to the permeation barrier. J Bacteriol 1985; 162: 9.
21. Wang Y, Hollingsworth RI. An NMR spectroscopy and molecular mechanics study of the molecular basis for the supramolecular structir of lipopolysaccharides. Biochemistry 1996; 35: 5647.
22. Takayama K, Din ZZ, Mukerjce P, Cooke PH, Kirkland TN. Physicochemical properties of the lipopolysaccharide unit that activates B lymphocytes. J Biol Chem 1990; 265: 14023.
23. Detmers PA, Thieblemont N, Vasselon T, Pironkova R, Miller DS, Wright SD. Potential role of membrane internalization and vesicle fusion in adhesion of neutrophils in response to lipopolysaccharide and TNF. J Immunol 1996; 157: 5589.
24. Yang RB, Mark MR, Gray A et al. Toll-like receptor-2 mediates lipopolysaccharide-induced cellular signalling. Nature 1998: 395: 284.