Synthesis of glycoconjugate polymer carrying globotriaose as artificial multivalent ligand for Shiga toxin-producing Escherichia coli O157: H7

Carbohydrate Polymers

Volumn 57, Issue 4, 2004, Pages 441-450

  Miyagawa, Atsushi ^a,b   Kurosawa, Hidehiro ^a   Watanabe, Toshiyuki ^a   Koyama, Tetsuo ^a   Terunuma, Daiyo ^a   Matsuoka, Koji ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

Author keywords

Carbohydrates; Escherichia coli; Globotriaose; Glycoconjugate polymer; Radical polymerization; Shiga toxins

Indexed keywords

GLOBOTRIAOSE; GLYCOCONJUGATE POLYMER; RADICAL POLYMERIZATIONS; SHIGA TOXINS;

CARBOHYDRATES; ESCHERICHIA COLI; MONOMERS; POLYMERIZATION; PROTEINS; SYNTHESIS (CHEMICAL);

POLYMERS;

ESCHERICHIA COLI;

EID: 4344563028     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2004.06.001     Document Type: Article

References (24)

1. Arya P., Kutterer K.M.K., Qin H., Roby J., Barnes M.L., Lin S., Lingwood C.A., Peter M.G. α Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosyl ceramide. Bioorganic and Medical Chemistry. 7:1999;2823-2833.
2. Austin P.W., Hardy F.E., Buchanan J.G., Baddiley J. 3,4,6-Tetra-O-benzyl- D-galactosyl chloride and its use in the synthesis of a- and b-D-galactopyranosides. Journal of the Chemical Society. 1965;1419-1424.
3. Bast D.J., Banerjee L., Clark C., Read R.J., Brunton J.L. The identification of three biologically relevant globotriaosyl ceramide receptor binding sites on the Verotoxin 1 B subunit. Molecular Microbiology. 32:1999;953-960.
4. k trisaccharide. The Journal of Organic Chemistry. 64:1999;9153-9163.
5. k-antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin. Bioorganic and Medical Chemistry. 7:1999;2053-2062.
6. Gestwicki J.E., Cairo C.W., Strong L.E., Oetjen K.A., Kiessling L.L. Influencing receptor-ligand binding mechanisms with multivalent ligand architecture. Journal of the American Chemical Society. 124:2002;14922-14933.
7. Kitov P.I., Sadowska J.M., Mulvey G., Armstrong G.D., Ling H., Pannu N.S., Read R.J., Bundle D.R. Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands. Nature. 403:2000;669-672.
8. Koto S., Morishima N., Miyata Y., Zen S. Preparation of 2,3,4,6-tetra-O-benzyl-D-mannose. Bulletin of the Chemical Society of Japan. 49:1976;2639-2640.
9. Lee R.T., Lee Y.C. Synthesis of 3-(2-aminoethylthio)propyl glycosides. Carbohydrate Research. 37:1974;193-201.
10. Lee Y.C., Lee R.T. Carbohydrate-protein interactions: basis of glycobiology. Accounts of Chemical Research. 28:1995;321-327.
11. 3. Biochemistry. 37:1998;1777-1788.
12. Matsuoka K., Nishimura S.-I. Synthetic glycoconjugates. 5. Polymeric sugar ligands available for determining the binding specificity of lectins. Macromolecules. 28:1995;2961-2968.
13. Matsuoka K., Terabatake M., Esumi Y., Terunuma D., Kuzuhara H. Synthetic assembly of trisaccharide moieties of globotriaosyl ceramide using carbosilane dendrimers as cores. A new type of functional glyco-material. Tetrahedron Letters. 40:1999;7839-7842.
14. Mylvaganam M., Lingwood C.A. Adamantyl globotriaosyl ceramide: a monovalent soluble mimic which inhibits verotoxin binding to its glycolipid receptor. Biochemical and Biophysical Research Communications. 257:1999;391-394.
15. Nishikawa K., Matsuoka K., Kita E., Okabe N., Mizuguchi M., Hino K., Miyazawa S., Yamasaki C., Aoki J., Takashima S., Yamakawa Y., Nishijima M., Terunuma D., Kuzuhara H., Natori Y. A therapeutic agent with oriented carbohydrates for treatment of infections by Shiga toxin-producing Escherichia coli O157:H7. Proceedings of the National Academy of Sciences. 88:2002;7669-7674.
16. Nishimura S.-I., Furuike T., Matsuoka K., Maruyama K., Nagata K., Kurita K., Nishi N., Tokura S. Synthetic glycoconjugates. 4. Use of ω-(acrylamido)alkyl glycosides for the preparation of cluster glycopolymers. Macromolecules. 27:1994;4876-4880.
17. Ogawa T., Nakabayashi S., Kitajima T. Synthesis of hexasaccharide unit of a complex type of glycan chain of a glycoprotein. Carbohydrate Research. 114:1983;225-236.
18. Roy R. Syntheses and some applications of chemically defined multivalent glycoconjugates. Current Opinion in Structural Biology. 6:1996;692-702.
19. Roy R., Tropper F.D. Synthesis of antigenic carbohydrate polymers recognized by lectins and antibodies. Journal of the Chemical Society. Chemical Communications. 1988;1058-1060.
20. Soltyk A.M., MacKenzie C.R., Wolski V.M., Hirama T., Kitov P.I., Bundle D.R., Brunton J.L. A mutational analysis of the globotriaosyl ceramide-binding sites of verotoxin VT1. The journal of Biological Chemistry. 277:2002;5351-5359.
21. Takano T., Nakatsubo F., Murakami K. A facile allyl β-glycosylation in the presence of a benzyl protecting group, using boron trifuoride etherate. Carbohydrate Research. 203:1990;341-342.
22. Turnbull W.B., Stoddart J.F. Design and synthesis of glycodendrimers. Reviews in Molecular Biotechnology. 90:2002;231-255.
23. Watanabe M., Matsuoka K., Kita E., Igai K., Higashi N., Miyagawa A., Watanabe T., Yanoshita R., Samejima Y., Terunuma D., Natori Y., Nishikawa K. Oral therapeutic agents with highly clustered globotriose for treatment of shiga toxigenic Escherichia coli infections. Journal of Infectious Diseases. 360:2004;355-359.
24. van Seeventer P.B., van Dorst J.A.L.M., Siemerink J.F., Kamerling J.P., Vliegenthart J.F.G. Thiol addition to protected allyl glycosides: an improved method for the preparation of spacer-arm glycosides. Carbohydrate Research. 300:1997;369-373.