Synthesis of Lipopolysaccharide, Peptidoglycan, and Lipoteichoic Acid Fragments

Comprehensive Glycoscience: From Chemistry to Systems Biology

Volumn 1-4, Issue , 2007, Pages 685-711

  Kusumoto, S ^a   Fukase, K ^b   Fujimoto, Y ^b  

^a SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77955117161     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044451967-2/00018-0     Document Type: Chapter

References (96)

1. Ghuysen J.M., Hackenbeck B. Bacterial Cell Wall. New Comprehensive Biochemistry 1994, Elsevier, Amsterdam. R. Hackenbeck (Ed.).
2. Hancock I., Poxon I. Bacterial Cell Surface Techniques 1988, John Wiley & Sons, Chichester.
3. Akira S., Takeda K. Nat. Rev. Immunol. 2004, 4:499-511.
4. Dziarski R. Cell. Mol. Life. Sci. 2003, 60:1793-1804.
5. Ezekowitz R.A.B., Hoffmann J.A. Innate Immunity 2003, Humana Press.
6. Schleifer K.H., Kandler O. Bacteriol. Rev. 1972, 36:407-477.
7. Gale E.F., Cundliffe E., Erynolds P.E., Richmond N.H., Waring M.J. The Molecular Basis of Antibiotic Action 1981, Wiley. 2nd Ed.
8. Dziarski R. Mol. Immunol. 2004, 40:877-886.
9. Dezelee P., Bricas E. Biochemistry 1970, 9:823-831.
10. Bricas E. Survey of Synthetic Work in the Field of the Bacterial Cell Wall Peptides. The Chemistry of Polypeptides 1973, 205-235. Plenum, New York. P.G. Katsuoyannis (Ed.).
11. Freund J., McDermott K. Proc. Soc. Expt. Biol. 1942, 49:548-553.
12. Ellouz F., Adam A., Ciorubaru R., Lederer E. Biochim. Biophys. Res. Commun. 1974, 59:1317-1325.
13. Kotani S., Watanabe Y., Shimono T., Narita T., Kato K., Stewart-Tull D.E.S., Kinoshita F., Yokogawa K., Kawata S., Shiba T., Kusumoto S., Tarumi Y. Z. Immun.-Forsch. 1975, 149:302-319.
14. Merser C., Sinay P., Adam A. Biochim. Biophys. Res. Commun. 1975, 66:1316-1322.
15. Kusumoto S., Tarumi Y., Ikenaka K., Shiba T. Bull. Chem. Soc. Jpn. 1976, 49:533-539.
16. Kubasch N., Schmidt R.R. Eur. J. Org. Chem. 2002, 2710-2726.
17. Roychowdhury A., Wolfert M.A., Boons G.-J. ChemBioChem. 2005, 6:2088-2097.
18. Inamura S., Fukase K., Kusumoto S. Tetrahedron Lett. 2001, 42:7613-7616.
19. Inage M., Chaki H., Kusumoto S., Shiba T. Tetrahedron Lett. 1980, 21:3889-3892.
20. Kusumoto S., Yoshimura H., Imoto M., Shimamoto T., Shiba T. Tetrahedron Lett. 1985, 26:909-912.
21. Inamura S., Fujimoto Y., Kawasaki A., Shiokawa Z., Woelk E., Heine H., Lindner B., Inohara N., Kusumoto S., Fukase K. Org. Biomol. Chem. 2006, 4:232-242.
22. Inohara N., Chamaillard M., McDonald C., Nunez G. Ann. Rev. Biochem. 2005, 74:355-383.
23. Chamaillard M., Girardin S.E., Viala J., Philpott D.J. Cell Microbiol. 2003, 5:581-592.
24. Chamaillard M., Hashimoto M., Horie Y., Masumoto J., Qiu S., Saab L., Ogura Y., Kawasaki A., Fukase K., Kusumoto S., Valvano M.A., Foster S.J., Mak T.W., Nunez G., Inohara N. Nat. Immunol. 2003, 4:702-707.
25. Inohara N., Ogura Y., Fontalba A., Gutierrez O., Pons F., Crespo J., Fukase K., Inamura S., Kusumoto S., Hashimoto M., Foster S.J., Moran A.P., Fernandez-Luna J.L., Nunez G. J. Biol. Chem. 2003, 278:5509-5512.
26. Kitaura Y., Nakaguchi O., Takeno H., Okada S., Yonishi S., Hemmi K., Mori J., Senoh H., Mine Y., Hashimoto M. J. Med. Chem. 1982, 25:335-337.
27. Hemmi K., Takeno H., Okada S., Nakaguchi O., Kitaura Y., Hashimoto M. J. Am. Chem. Soc. 1981, 103:7026-7028.
28. Morrison D.C., Ryan J.L. Bacterial Endotoxic Lipopolysaccharide. Molecular Biochemical and Cellular Biology 1992, vol. 1. CRC Press, Boca Raton.
29. Brade H., Opal S.M., Vogel S.N., Morrison D.C. Endotoxin in Health and Disease 1999, Marcel Dekker, New York.
30. Nikaido H. Microbiol. Mol. Biol. Rev. 2003, 67:593-656.
31. Pffeifer R. Z. Hygiene 1892, 11:393-412.
32. Vaara M. Lipopolysaccharide and the Permeability of the Bacterial Outer Membrane. Endotoxin in Health and Disease 1999, 31-38. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
33. Westphal O., Lüderitz O. Z. Naturforsch. 1952, 7:548-555.
34. Rietschel E.T., Westphal O. Endotoxin: Historical Perspectives. Endotoxin in Health and Disease 1999, 1-31. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
35. Zähringer U., Lindner B., Rietschel E.Th. Chemical Structure of Lipid A: Recent Advance in Structural Analysis of Biologically Active Molecules. Endotoxin in Health and Disease 1999, 93-114. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
36. Zähringer U., Lindner B., Rietschel E.Th. Adv. Carbohydr. Chem. Biochem. 1994, 50:211-276.
37. Imoto M., Kusumoto S., Shiba T., Rietschel E.Th., Galanos C., Lüderitz O. Tetrahedron Lett. 1985, 26:907-908.
38. Imoto M., Yoshimura H., Yamamoto M., Shimamoto T., Kusumoto S., Shiba T. Bull. Chem. Soc. Jpn. 1987, 60:2197-2204.
39. Imoto M., Yoshimura H., Sakaguchi N., Kusumoto S., Shiba T. Tetrahedron Lett. 1985, 26:1545-1548.
40. Imoto M., Yoshimura H., Shimamoto T., Sakaguchi N., Kusumoto S., Shiba T. Bull. Chem. Soc. Jpn. 1987, 60:2205-2214.
41. Tai A., Nakahata M., Harada H., Izumi Y., Kusumoto S., Inage M., Shiba T. Chem. Lett. 1980, 1125-1126.
42. Galanos C., Lüderitz O., Rietschel E.Th., Westphal O., Brade H., Brade L., Freudenberg M., Schade U., Imoto M., Yoshimura H., Kusumoto S., Shiba T. Eur. J. Biochem. 1985, 148:1-5.
43. Kusumoto S., Fukase K., Oikawa M. The Chemical Synthesis of Lipid A. Endotoxin in Health and Disease 1999, 243-256. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
44. Liu W.-C., Oikawa M., Fukase K., Suda Y., Winarno H., Mori S., Hashimoto M., Kusumoto S. Bull. Chem. Soc. Jpn. 1997, 70:1441-1450.
45. Watanabe Y., Kodama Y., Ebysuya K., Ozaki S. Tetrahedron Lett. 1990, 31:255-256.
46. Noyori R., Ohkuma T., Kitamura M., Takaya H., Sayo N., Kumobayashi H., Akutagawa S. J. Am. Chem. Soc. 1987, 109:5856-5858.
47. Oikawa M., Kusumoto S. Tetrahedron: Asymm. 1995, 6:961-966.
48. Oikawa M., Wada A., Yoshizaki H., Fukase K., Kusumoto S. Bull. Chem. Soc. Jpn. 1997, 70:1435-1440.
49. Qureshi N., Mascagni P., Ribi E., Takayama K. J. Biol. Chem. 1985, 260:5271-5278.
50. Meyers K.R., Truchor A.T., Wald J., Hudson Y., Ulrich J.T. A Critical Determinant Lipid A Endotoxic Activity. Cellular and Molecular Aspects of Endotoxin Reactions 1990, vol. 1:145-156. Elsevier, Amsterdam. A. Nowotony, J.J. Spitzer, E.J. Ziegler (Eds.).
51. Johnson D.A., Keegan D.S., Sowell C.G., Livesay M.T., Johnson C.L., Taubner L.M., Harris A., Meyers K.R., Thompson J.D., Gustafson G.L., Rhodes M.J., Ulrich J.T., Ward J.R., Yorgensen Y.M., Cantrel J.L., Brookshire V.G. J. Med. Chem. 1999, 42:4640-4649.
52. Demchenko A.V., Wolfelt M.A., Santhanam B., Moore J.N., Boons G.-J. J. Am. Chem. Soc. 2003, 125:6103-6112.
53. Suda Y., Ogawa T., Kashihara W., Oikawa M., Shimoyama T., Hayashi T., Tamura T., Kusumoto S. J. Biochem. 1997, 121:1129-1133.
54. Sakai Y., Oikawa M., Yoshizaki H., Ogawa T., Suda Y., Fukase K., Kusumoto S. Tetrahedron Lett. 2000, 41:6843-6847.
55. Ogawa T., Asai Y., Sakai Y., Oikawa M., Fukase K., Suda Y., Kusumoto S., Tamura T. FEMS Immunol. Microbiol. 2003, 36:1-7.
56. Knirel Y.A., Dentovskaya S.V., Sentchenkova S.N., Shaikhutdinova R.Z., Kocharova N.A., Anisimov A.P. J. Endotoxin Res. 2006, 12:3-9.
57. Kawahara K., Tsukano H., Watanabe H., Lindner B., Matsuura M. Infect. Immun. 2002, 70:4092-4098.
58. Knirel Y.A., Lindner B., Vinogradov E.V., Kocharova N.A., Sentchenkova S.N., Shaikhutdinova R.Z., Dentovskaya S.V., Fursova N.K., Bakhteeva I.V., Titareva G.M., Balakhnov S.V., Holst O., Gremyakova T.A., Pier G.B., Anisimov A.P. Biochemistry 2005, 44:1731-1743.
59. Seydel U., Wiese A., Schrom A.B., Brandenburg K.A. Biophysical View on the Function and Activity of Endotoxin. Endotoxin in Health and Disease 1999, 195-219. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
60. Wang Y., Hollingworth R.I. Biochemistry 1996, 35:5647-5654.
61. Oikawa M., Shintaku T., Fukuda N., Seklijic H., Fukase Y., Yoshizaki H., Fukase K., Kusumoto S. Org. Biomol. Chem. 2004, 2:3557-3565.
62. Takada H., Kotani S. CRC Critical Rev. Microbiol. 1989, 16:477-523.
63. Akashi S., Nagai Y., Ogata H., Oikawa M., Fukase K., Kusumoto S., Kawasaki K., Nishijima M., Hayashi S., Kimoto M., Miyake K. Int. Immun. 2001, 13:1595-1599.
64. Kobayashi M., Saitoh S., Tanimura N., Takahashi K., Kawasaki K., Nishijima M., Fujimoto Y., Fukase K., Akashi-Takamura S., Miyake K. J. Immunol. 2006, 176:6211-6218.
65. Triantafilou M., Brandenburg K., Kusumoto S., Fukase K., Mackie A., Seydel U., Triantafilou K. Biochem. J. 2004, 381:527-536.
66. Triantafilou M., Triantafilou K. J. Endotoxin Res. 2005, 11:6-11.
67. Kusama T., Soga T., Shioya E., Nakayama K., Nakajima H., Osada Y., Ono Y., Kusumoto S., Shiba T. Chem. Pharm. Bull. 1990, 38:3366-3372.
68. Fukase K., Kirikae T., Kirikae F., Liu W.-C., Oikawa M., Suda Y., Kurosawa M., Fukase Y., Yoshizaki H., Kusumoto S. Bull. Chem. Soc. Jpn. 2001, 74:2189-2197.
69. Salimath P.V., Weckesser J., Strittmatter W., Mayer H. Eur. J. Biochem. 1983, 136:195-200.
70. Qureshi N., Honovich J.P., Hara H., Cotter R.J., Takayama K. J. Biol. Chem. 1988, 263:5502-5504.
71. Christ W.J., McGuiness P.D., Asano O., Wang Y., Mullarkey M.A., Perez M., Hawkins L.D., Blythe T.A., Dubuc G.R., Robidoux A.L. J. Am. Chem. Soc. 1994, 116:3637-3638.
72. Christ W.J., Asano O., Robidoux A.L., Perez M., Wang Y., Dubuc G.R., Gabin W.E., Hawkins L.D., McGuiness P.D., Mullarkey M.A., Lewis M.D., Kishi Y., Kawata T., Bristol J.R., Rose J.R., Rossignor D.P., Kobayashi S., Hashinuma I., Kimura A., Asakawa N., Katayama K., Yamatsu I. Science 1995, 268:80-83.
73. Zähringer U., Lindner B., Seydel U., Rietschel E.Th., Naoki H., Unger F.M., Imoto M., Kusumoto S., Shiba T. Tetrahedron Lett. 1985, 26:6321-6324.
74. Yoshizaki H., Fukuda N., Sato K., Oikawa M., Fukase K., Suda Y., Kusumoto S. Angew. Chem. Int. Ed. 2001, 40:1475-1480.
75. Imoto M., Kusumoto S., Shiba T. Tetrahedron Lett. 1987, 28:6235-6238.
76. Imoto M., Kusunose N., Matsuura Y., Kusumoto S., Shiba T. Tetrahedron Lett. 1987, 28:6277-6280.
77. van der Klein J.H., Boons G.J.P.H., Veeneman G.H., van Boom J.H. Tetrahedron Lett. 1989, 30:5477-5480.
78. Fischer W. Bacterial Phospholipids and Lipoteichoic Acid. Glycolipids, Phosphoglycolipids, and Sulfoglycolipids; Handbook of Lipid Research 1990, 123-234. Plenum, New York. M. Kates (Ed.).
79. Fischer W. Med. Microbiol. Immunol. 1994, 183:61-76.
80. Usami H., Yamamoto A., Sugawara Y., Hamada S., Yamamoto T., Kato K., Kokeguchi S., Takeda H., Kotani S. Br. J. Cancer 1987, 56:797-799.
81. Tsutsui O., Kokeguchi S., Matsumura T., Kato K. FEMS Microbiol. Immun. 1991, 76:211-218.
82. Oltvoort J.J., Kloosterman M., Constant A.A., van Boeckel A.A., van Boom J.H. Carbohydr. Res. 1984, 130:147-163.
83. Fukase K., Matsumoto T., Ito N., Yoshimura T., Kotani S., Kusumoto S. Bull. Chem. Soc. Jpn. 1992, 65:2643-2654.
84. Fukase K., Yoshimura T., Kotani S., Kusumoto S. Bull. Chem. Soc. Jpn. 1994, 67:473-482.
85. Fukase K., Tanaka H., Torii S., Kusumoto S. Tetrahedron Lett. 1990, 31:389-392.
86. Fukase K., Yoshimura T., Hashida M., Kusumoto S. Tetrahedron Lett. 1991, 32:4019-4022.
87. Suda Y., Tochio H., Kawano K., Takada H., Yoshida T., Kotani S., Kusumoto S. FEMS Imunol. Med. Microbiol. 1995, 12:97-112.
88. Stadejmeier A., Morath S., Hartung T., Schmidt R.R. Angew. Chem. Int. Ed. 2003, 42:916-920.
89. Figueroa-Perez I., Stadejmeier A., Morath S., Hartung T., Schmidt R.R. Tetrahed. Asymm. 2005, 16:493-506.
90. Morath S., Stadelmaier A., Geyer A., Schmidt R.R., Hartung T. J. Exp. Med. 2002, 195:1635-1640.
91. Deoninger S., Stadejmeier A., von Aulock S., Morath S., Schmidt R.R., Hartung T. J. Immunol. 2003, 170:4134-4138.
92. Hashimoto M., Tawaratsumida K., Kariya H., Aoyama K., Tamura T., Suda T. Internat. Immunol. 2005, 18:355-362.
93. Hashimoto M., Tawaratsumida K., Kariya H., Kiyohara A., Suda Y., Kirikae F., Kirikae T., Goetz F. J. Immunol. 2006, 177:3162-3169.
94. Takada H., Kotani S. Immunopharmacological Activities of Synthetic Muramyl-Peptides. Immunology of the Bacterial Cell Envelope 1985, 119-152. John Wiley and Sons, Chichester. D.E.S. Stewart-Tull, M. Davies (Eds.).
95. Raetz C.R.H., Whitfield C. Annu. Rev. Biochem. 2002, 71:635-700.
96. Raetz C.R.H., Garrett T.A., Reynolds C.M., Shaw W.A., Moore J.D., Smith D.C., Ribeiro A.A., Murphy R.C., Ulevitch R.J.C., Fearns D., Reichart C.K., Glass C., Benner S., Subramaniam R., Harkewicz R., Bowers-Gentry C., Buczynski M.W., Cooper J.A., Deems R.A., Dennis E.A. Lipid Res. 2006, 47:1097-1111.