Practical synthesis of fully protected globotriaose and its glycopolymers

Carbohydrate Polymers

Volumn 69, Issue 2, 2007, Pages 326-335

  Matsuoka, Koji ^a   Goshu, Yusuke ^a   Takezawa, Yutaka ^a   Mori, Tomonori ^a   Sakamoto, Jun Ichi ^a   Yamada, Akihiro ^a   Onaga, Tomotsune ^a   Koyama, Tetsuo ^a   Hatano, Ken ^a   Snyder, Philip W ^b   Toone, Eric J ^b   Terunuma, Daiyo ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b DUKE UNIVERSITY   (United States)

Author keywords

Globotriaose; Glycoclusters; Glycopolymers; Glycosides; Polymerization

Indexed keywords

AMIDES; CARBOHYDRATES; FREE RADICAL POLYMERIZATION; HOMOPOLYMERIZATION; MONOMERS; SYNTHESIS (CHEMICAL);

ACRYLAMIDES; GLOBOTRIAOSE; GLYCOCLUSTERS; GLYCOPOLYMERS; GLYCOSIDES;

BIOPOLYMERS;

EID: 34247220372     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2006.10.011     Document Type: Article

References (27)

1. Austin P.W., Hardy F.E., Buchanan J.G., and Baddiley J. 2,3,4,6-Tetra-O-benzyl-d-galactopyranosyl chloride and its use in synthesis of α- and β-d-galactopyranosides. Journal of the Chemical Society 1965 (1965) 1419-1424
2. Beith-Halahmi D., Flowers H.M., and Shapiro D. Synthesis of O-β-d-galactopyranosyl-(1 → 3)-O-β-d-galactopyranosyl-(1 → 4)-d-glucose. Carbohydrate Research 5 (1967) 25-30
3. Dubber M., and Lindhorst T.K. Synthesis of octopus glycosides: core molecules for the construction of glycoclusters and carbohydrate-centered dendrimers. Carbohydrate Research 310 (1998) 35-41
4. Jung K.-H., Hoch M., and Schmidt R.R. Selectively protected lactose and 2-azido lactose, building blocks for glycolipid synthesis. Liebigs Annalen Der Chemie 1989 (1989) 1099-1106
5. Kamath V.P., Yeske R.E., Gregson J.M., Ratcliffe R.M., Fang Y.R., and Palcic M.M. Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide. Carbohydrate Research 339 (2004) 1141-1146
6. Karmali M.A. Infection by verocytotoxin-producing Escherichia coli. Clinical Microbiology Reviews 2 (1989) 15-38
7. Kim W.-S., Hosono S., Sasai H., and Shibasaki M. Rare earth perchlorate catalized glycosidation of glycosyl fluorides with trimethylsilyl ethers. Tetrahedron Letters 36 (1995) 4443-4446
8. Kimura T., Xue F., Kobayashi T., Onoda T., and Yamamoto H. Trial production and evaluation of gel permeation chromatograph equipped with on-line distiller for mobile phase recycling. Polymer Journal 36 (2004) 205-208
9. Koike K., Sugimoto M., Sato S., Ito Y., Nakahara Y., and Ogawa T. Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide. Carbohydrate Research 163 (1987) 189-208
10. Lingwood C.A. Verotoxins and their glycolipid receptors. Advances in Lipid Research 25 (1993) 189-211
11. Lipták A., Jodál I., and Nánási P. Hydrogenolysis of benzylidene acetals: synthesis of benzyl 2,3,6,2′,3′,4′-hexa-O-benzyl-β-cellobioside, -maltoside, and -lactoside, benzyl 2,3,4,2′,3′,4′-hexa-O-benzyl-β-allolactoside, and benzyl 2,3,6,2′,3′,6′-hexa-O-benzyl-β-lactoside. Carbohydrate Research 52 (1976) 17-22
12. Matsuoka K., Nishimura S.-I., and Lee Y.C. Synthesis of bi-fluorescence-labeled lactoside: a substrate for continual assay of ceramide glycanase. Tetrahedron: Asymmetry 5 (1994) 2335-2338
13. Matsuoka K., and Nishimura S.-I. Synthetic glycoconjugates. 5. polymeric sugar ligands available for determining the binding specificity of lectins. Macromolecules 28 (1995) 2961-2968
14. Matsuoka K., Terabatake M., Esumi Y., Terunuma D., and Kuzuhara H. Synthetic assembly of trisaccharide moieties of globotriaosyl ceramide using carbosilane dendrimers as cores. a new type of functional glyco-materials. Tetrahedron Letters 40 (1999) 7839-7842
15. Matsuoka K., Terabatake M., Umino A., Esumi Y., Hatano K., Terunuma D., et al. Carbosilane dendrimers bearing globotriaoses: syntheses of globotrioasyl derivative and introduction into carbosilane dendrimers. Biomacromolecules 7 (2006) 2274-2283
16. Matsuoka K., Terabatake M., Esumi Y., Hatano K., Terunuma D., and Kuzuhara H. Carbosilane dendrimers bearing globotriaoses: construction of a series of carbosilane dendrimers bearing globotriaoses. Biomacromolecules 7 (2006) 2284-2290
17. Miyagawa A., Kurosawa H., Watanabe T., Koyama T., Terunuma D., and Matsuoka K. Synthesis of glycoconjugate polymer carrying globotriaose as artificial multivalent ligand for Shiga toxin-producing Escherichia coli O157: H7. Carbohydrate Polymers 51 (2004) 441-450
18. Nishikawa K., Matsuoka K., Kita E., Okabe N., Mizuguchi M., Hino K., et al. 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 of the United States of America. 99 (2002) 7669-7674
19. Nishikawa K., Matsuoka K., Watanabe M., Igai K., Hino K., Hatano K., et al. Identification of the optimal structure required for a Shiga toxin neutralizer with oriented carbohydrates to function in the circulation. Journal of Infectious Diseases 191 (2005) 2097-2105
20. 3). Liebigs Annalen Der Chemie 1992 (1992) 217-224
21. Richtmyer N.K. Benzyl heptaacetyl-β-lactoside. Journal of American Chemical Society 68 (1946) 1136-1137
22. Sandvig K. Shiga toxins. Toxicon 39 (2001) 1629-1635
23. Sarkar A.K., and Roy N. Synthesis of O-(β-d-glucopyranosyluronic acid)-(1 → 4)-O-β-d-galactopyranosy-(1 → 4)-d-glucopyranose. Carbohydrate Research 163 (1987) 285-288
24. Sarkar A.K., and Matta K.L. 2,3,4,6-Tetra-O-benzyl-β-d-galactopyranosyl phenyl sulfoxide as a glycosyl donor. Synthesis of some oligosaccharides containing an α-d-galactopyranosy group. Carbohydrate Research 233 (1992) 245-250
25. Takano T., Nakatsubo F., and Murakami K. A facile allyl β-glycosylation in the presence of a benzyl protecting group, using bron trifluoride etherate. Carbohydrate Research 203 (1990) 341-342
26. Watanabe M., Matsuoka K., Kita E., Igai K., Higashi N., Miyagawa A., et al. Oral therapeutic agents with highly clustered globotriose for treatment of Shiga toxigenic Escherichia coli infections. Journal of Infectious Diseases 189 (2004) 360-368
27. Watanabe M., Igai K., Matsuoka K., Miyagawa A., Watanabe T., Yanoshita R., et al. Structural analysis of the interaction between Shiga toxin B subunits and linear polymers bearing clustered globotriose residues. Infection and Immunity 74 (2006) 1984-1988