Self and nonself recognition with bacterial and animal glycans, surveys by synthetic chemistry

Methods in Enzymology

Volumn 478, Issue C, 2010, Pages 323-342

  Fujimoto, Yukari ^a   Tanaka, Katsunori ^a   Shimoyama, Atsushi ^a   Fukase, Koichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE RECRUITMENT DOMAIN PROTEIN 15; DIAMINOPIMELIC ACID; DISACCHARIDE; GLYCAN; GLYCOCONJUGATE; GLYCOPROTEIN; INTERLEUKIN 6; LIPID A DERIVATIVE; LIPOPOLYSACCHARIDE; MURAMYL DIPEPTIDE; PEPTIDE; PEPTIDOGLYCAN; SIALIC ACID;

ANIMAL CELL; BACTERIUM; BIOLOGICAL ACTIVITY; BLOOD; BOOK; CELL CULTURE; CELL SURFACE; CHEMISTRY; CONTROLLED STUDY; ESCHERICHIA COLI; GLYCOSYLATION; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HELICOBACTER PYLORI; HUMAN; HUMAN CELL; IMMUNE SYSTEM; IN VIVO STUDY; INFLAMMATION; INNATE IMMUNITY; MOLECULAR EVOLUTION; MOUSE; NONHUMAN; PORPHYROMONAS GINGIVALIS; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RABBIT; RECOGNITION; STRUCTURE ACTIVITY RELATION;

ANIMALIA; BACTERIA (MICROORGANISMS); HELICOBACTER PYLORI; NEGIBACTERIA; POSIBACTERIA;

EID: 77956294598     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(10)78016-2     Document Type: Chapter

References (38)

1. 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., et al. An essential role for NOD1 in host recognition of bacterial peptidoglycan containing diaminopimelic acid. Nat. Immunol. 2003, 4:702-707.
2. Chen W.C., Completo G.C., Paulson J.C. Targeting of human B lymphoma with cytotoxic liposomes containing glycan ligands of CD22. Glycobiology 2008, 18:963.
3. Elliott S., Lorenzini T., Asher S., Aoki K., Brankow D., Buck L., Busse L., Chang D., Fuller J., Grant J., Hernday N., Hokum M., et al. Enhancement of therapeutic protein in vivo activities through glycoengineering. Nat. Biotechnol. 2003, 21:414-421.
4. Fujimoto Y., Adachi Y., Akamatsu M., Fukase Y., Kataoka M., Suda Y., Fukase K., Kusumoto S. Synthesis of lipid A and its analogues for investigation of the structural basis for their bioactivity. J. Endotoxin Res. 2005, 11:341-347.
5. Fujimoto Y., Iwata M., Imakita N., Shimoyama A., Suda Y., Kusumoto S., Fukase K. Synthesis of immunoregulatory Helicobacter pylori lipopolysaccharide partial structures. Tetrahedron Lett. 2007, 48:6577-6581.
6. Girardin S.E., Boneca I.G., Carneiro L.A., Antignac A., Jehanno M., Viala J., Tedin K., Taha M.K., Labigne A., Zahringer U., Coyle A.J., DiStefano P.S., et al. Nod1 detects a unique muropeptide from gram-negative bacterial peptidoglycan. Science 2003, 300:1584-1587.
7. Girardin S.E., Boneca I.G., Viala J., Chamaillard M., Labigne A., Thomas G., Philpott D.J., Sansonetti P.J. Nod2 is a general sensor of peptidoglycan through muramyl dipeptide (MDP) detection. J. Biol. Chem. 2003, 278:8869-8872.
8. Hirai M., Minematsu H., Kondo N., Oie K., Igarashi K., Yamazaki N. Accumulation of liposome with Sialyl Lewis X to inflammation and tumor region: Application to in vivo bio-imaging. Biochem. Biophys. Res. Commun. 2007, 353:553-558.
9. Inamura S., Fukase K., Kusumoto S. Synthetic study of peptidoglycan partial structures. Synthesis of tetrasaccharide and octasaccharide fragments. Tetrahedron Lett. 2001, 42:7613-7616.
10. Inamura S., Fujimoto Y., Kawasaki A., Shiokawa Z., Woelk E., Heine H., Lindner B., Inohara N., Kusumoto S., Fukase K. Synthesis of peptidoglycan fragments and evaluation of their biological activity. Org. Biomol. Chem. 2006, 4:232-242.
11. 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., et al. Host recognition of bacterial muramyl dipeptide mediated through NOD2. Implications for Crohn's disease. J. Biol. Chem. 2003, 278:5509-5512.
12. Kamerling J.P., Boons G.J., Lee Y.C., Suzuki A., Taniguchi N., Voragen A.G.J. Analysis of glycans, polysaccharide functional properties & biochemistry of glycoconjugate glycans, carbohydrate-mediated interactions. Comprehensive Glycoscience, From Chemistry to Systems Biology, Vol II & III 2007, Elsevier, UK.
13. Kaneko T., Goldman W.E., Mellroth P., Steiner H., Fukase K., Kusumoto S., Harley W., Fox A., Golenbock D., Silverman N. Monomeric and polymeric gram-negative peptidoglycan but not purified LPS stimulate the Drosophila IMD pathway. Immunity 2004, 20:637-649.
14. Kaneko Y., Nimmerjahn F., Ravetch J.V. Anti-inflammatory activity of immunoglobulin G resulting from Fc sialylation. Science 2006, 313:670-673.
15. Kawasaki A., Karasudani Y., Otsuka Y., Hasegawa M., Inohara N., Fujimoto Y., Fukase K. Synthesis of diaminopimelic acid-containing peptidoglycan fragments and tracheal cytotoxin (TCT) for investigation of their biological functions. Chem. Eur. J. 2008, 14:10318-10330.
16. Kusumoto S., Fukase K. Synthesis of endotoxic principle of bacterial lipopolysaccharide and its recognition by the innate immune systems of hosts. Chem. Rec. 2006, 6:333-343.
17. Kusumoto S., Fukase K., Oikawa M. The chemical synthesis of lipid A. Endotoxin Health Dis. 1999, 243-256.
18. Kusumoto S., Fukase K., Fujimoto Y. Chemical synthesis of bacterial lipid A. Microb. Glycobiol.: Struct. Relevance Appl. 2009, 415-427.
19. Lee Y.C., Townsend R.R., Hardy M.R., Lonngren J., Arnarp J., Haraldsson M., Lonn H. Binding of synthetic oligosaccharides to the hepatic Gal/GalNAc lectin. Dependence on fine structural features. J. Biol. Chem. 1983, 258:199-202.
20. Magalhaes J.G., Philpott D.J., Nahori M.A., Jehanno M., Fritz J., Le Bourhis L., Viala J., Hugot J.P., Giovannini M., Bertin J., Lepoivre M., Mengin-Lecreulx D., et al. Murine Nod1 but not its human orthologue mediates innate immune detection of tracheal cytotoxin. EMBO Rep. 2005, 6:1201-1207.
21. Morell A.G., Irvine R.A., Sternlieb I., Scheinberg I.H., Ashwell G. Physical and chemical studies on ceruloplasmin V. Metabolic studies on sialic acid-free ceruloplasmin in vivo. J. Biol. Chem. 1968, 243:155-159.
22. Nakagawa T., Uozumi N., Nakano M., Mizuno-Horikawa Y., Okuyama N., Taguchi T., Gu J., Kondo A., Taniguchi N., Miyoshi E. Fucosylation of N-glycans regulates the secretion of hepatic glycoproteins into bile ducts. J. Biol. Chem. 2006, 281:29797-29806.
23. Ogawa T., Asai Y., Sakai Y., Oikawa M., Fukase K., Suda Y., Kusumoto S., Tamura T. Endotoxic and immunobiological activities of a chemically synthesized lipid A of Helicobacter pylori strain 206-1. FEMS Immunol. Med. Microbiol. 2003, 36:1-7.
24. Park E.I., Mi Y., Unverzagt C., Gabius H.J., Baenziger J.U. The asialoglycoprotein receptor clears glycoconjugates terminating with sialic acid alpha 2, 6GalNAc. Proc. Natl. Acad. Sci. USA 2005, 102:17125-17129.
25. Raetz C.R., Whitfield C. Lipopolysaccharide endotoxins. Annu. Rev. Biochem. 2002, 71:635-700.
26. Sakai Y., Oikawa M., Yoshizaki H., Ogawa T., Suda Y., Fukase K., Kusumoto S. Synthesis of Helicobacter pylori lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group. Tetrahedron Lett. 2000, 41:6843-6847.
27. Sato M., Furuike T., Sadamoto R., Fujitani N., Nakahara T., Niikura K., Monde K., Kondo H., Nishimura S. Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity. J. Am. Chem. Soc. 2004, 126:14013-14022.
28. Schleifer K.H., Kandler O. Peptidoglycan types of bacterial cell walls and their taxonomic implications. Bacteriol. Rev. 1972, 36:407-477.
29. Stenbak C.R., Ryu J.H., Leulier F., Pili-Floury S., Parquet C., Herve M., Chaput C., Boneca I.G., Lee W.J., Lemaitre B., Mengin-Lecreulx D. Peptidoglycan molecular requirements allowing detection by the Drosophila immune deficiency pathway. J. Immunol. 2004, 173:7339-7348.
30. Suda Y., Tochio H., Kawano K., Takada H., Yoshida T., Kotani S., Kusumoto S. Cytokine-inducing glycolipids in the lipoteichoic acid fraction from Enterococcus hirae ATCC 9790. FEMS Immunol. Med. Microbiol. 1995, 12:97-112.
31. Takada H., Kotani S. Vol: I Molecular Biochemistry and Cellular Biology 1992, CRC Press, Boca Raton.
32. Tanaka K., Fukase K. PET (positron emission tomography) imaging of biomolecules using metal-DOTA complexes: A new collaborative challenge by chemists, biologists, and physicians for future diagnostics and exploration of in vivo dynamics. Org. Biomol. Chem. 2008, 6:815-828.
33. Tanaka K., Masuyama T., Hasegawa K., Tahara T., Mizuma H., Wada Y., Watanabe Y., Fukase K. A submicrogram-scale protocol for biomolecule-based PET imaging by rapid 6Π-azaelectrocyclization: visualization of sialic acid dependent circulatory residence of glycoproteins. Angew. Chem. Int. Ed. 2008, 47:102-105.
34. Tanaka K., Minami K., Tahara T., Fujii Y., Siwu E.R.O., Nozaki S., Onoe H., Yokoi S., Koyama K., Watanabe Y., Fukase K. Electrocyclization-based labeling allows efficient in vivo imaging of cellular trafficking. ChemMedChem 2010, 5:841-845.
35. Varki A., Angata T. Siglecs-The major subfamily of I-type lectins. Glycobiology 2006, 16:1R-27R.
36. Vyas S.P., Singh A., Sihorkar V. Ligand-receptor-mediated drug delivery: An emerging paradigm in cellular drug targeting. Crit. Rev. Ther. Drug Carrier Syst. 2001, 18:1-76.
37. Yano T., Mita S., Ohmori H., Oshima Y., Fujimoto Y., Ueda R., Takada H., Goldman W.E., Fukase K., Silverman N., Yoshimori T., Kurata S. Autophagic control of listeria through intracellular innate immune recognition in Drosophila. Nat. Immunol. 2008, 9:908-916.
38. Yoshizaki H., Fukuda N., Sato K., Oikawa M., Fukase K., Suda Y., Kusumoto S. First total synthesis of the Re-type lipopolysaccharide. Angew. Chem. Int. Ed. Engl. 2001, 40:1475-1480.