Chemoenzymatic synthesis and lectin binding properties of dendritic N-acetyllactosamine

Bioconjugate Chemistry

Volumn 8, Issue 2, 1997, Pages 187-192

  Zanini, Diana ^a   Roy, René ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING ENERGY; BIOSYNTHESIS; PROTEINS;

BINDING PROPERTIES; CARBOHYDRATE-PROTEIN INTERACTIONS; CHEMO-ENZYMATIC SYNTHESIS; DENDRITICS; LECTIN BINDING; MONOMERICS; MULTIVALENCY; N-ACETYLGLUCOSAMINE; SOLID PHASIS; VALENCIES;

DENDRIMERS;

ERYTHRINA CRISTAGALLI; SUIDAE; TRITICUM AESTIVUM;

EID: 0031104859     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970005u     Document Type: Article

References (35)

1. Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3, 97.
2. Toone, E. J. (1994) Structure and energetics of protein-carbohydrate complexes. Curr. Opin. Struct. Biol. 4, 719.
3. Lee, Y. C. (1992). Biochemistry of carbohydrate-protein interaction. FASEB J. 6, 3193.
4. (a) Roy, R., and Laferrière, C. A. (1988) Synthesis of antigenic coplymers of N-acetylneuraminic acid binding to wheat germ agglutinin and antibodies. Carbohydr. Res. 177, C1.
5. (b) Gamian, A., Chomik, M., Laferrière, C. A., and Roy, R. (1991) Inhibition of Influenza A virus hemagglutinin and induction of interferon by synthetic sialylated glycoconjugates. Can. J. Microbiol. 37, 233.
6. (c) Roy, R., Andersson, F. O., Harms, G., Kelm, S., and Schauer, R. (1992) Synthesis of esterase-resistant 9-O-acetylated polysialosides as inhibitors of Influenza C virus hemagglutinin. Angew. Chem., Int. Ed. Engl. 31, 1478.
7. (d) Byramova, N. E., Mochalova, L. V., Belyanchikov, I. M., Matrosovich, M. N., and Bovin, N. V. (1991) Synthesis of sialic acid pseudopolysaccharides by coupling of spacer connected Neu5Ac with activated polymer. J. Carbohydr. Chem. 10, 691.
8. (e) Sigal, G. B., Mammen, M., Dahmann, G., and Whitesides, G. M. (1996) Polyacrylamides bearing pendant alpha-sialoside groups strongly inhibit agglutination of erythrocytes by Influenza virus - the strong inhibition reflects enhanced binding through cooperative polyvalent interactions. J. Am. Chem. Soc. 118, 3789 and references cited therein.
9. (a) Roy, R., Zanini, D., Meunier, S., and Romanowska, A. (1993) Solid-phase synthesis of dendritic sialoside inhibitors of Influenza A virus haemagglutinin. J. Chem. Soc., Chem. Commun., 1869.
10. (b) Roy, R., Zanini, D., Meunier, S., and Romanowska, A. (1994) Synthesis and antigenic properties of sialic acid based dendrimers. ACS Symp. Ser. 560, 104.
11. Lee, R. T., and Lee, Y. C. (1994) in Neoglycoconjugates: Preparations and Applications (Y. C. Lee and R. T. Lee, Eds.) p 23, Academic Press, San Diego.
12. Ando, K., Kikugawa, K., and Beppu, M. (1994) Involvement of sialylated poly-N-acetyllactosaminyl sugar chains of band 3 glycoprotein on senescent erythrocytes in anti-band 3 autoantibody binding. J. Biol. Chem. 269, 19394.
13. X determinants. J. Biol. Chem. 264, 9476.
14. Kawakami, H., Ito, M., Miura, Y., and Hirano, H. (1994) Involvement of N-acetyllactosamine containing sugar structures in the liver metastasis of mouse colon carcinoma (colon 26) cells. J. Gastroenterol. Hepatol. 9, 567.
15. Fenouillet, E., Thibault, V., and Miquelis, R. (1995) On the relationship between completion of N-acetyllactosamine oligosaccharide units and iodine content of thyroglobulin: a reinvestigation. Endocrinology 136, 4204.
16. Melaugh, W., Phillips, N. J., Campagnari, A. A., Tullius, M. V., and Gibson, B. W. (1994) Structure of the major oligosaccharide from the liposaccharide of Hemophilus ducreyi strain 35000 and evidence for additional glycoforms. Biochemistry 33, 13070.
17. Panjwani, N., Zhao, Z., Ahmad, S., Yang, Z. T., Jungalwala, F., and Baum, J. (1995) Neolacto-glycosphingolipids, potential mediators of corneal epithelial cell migration. J. Biol. Chem. 270, 14015.
18. (a) Schuster, M., Wang, P., Paulson, J. C., and Wong, C.-H. (1994) Solid-phase chemical-enzymatic synthesis of glycopeptides and oligosaccharides. J. Am. Chem. Soc. 116, 1135.
19. (b) Unverzagt, C., Keim, S., and Paulson, J. C. (1994) Chemical and enzymatic synthesis of multivalent sialoglycopeptides. Carbohydr. Res. 251, 285,
20. (c) Nishimura, S.-I., Matsuoka, K., and Lee, Y. C. (1994) Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier. Tetrahedron Lett. 31. 5657 and references cited therein.
21. (a) Roy, R. (1996) Glycodendrimers: a new class of biopolymers. Polym. News 21, 226.
22. (b) Roy, R. (1996) Syntheses and some applications of chemically defined multivalent glycoconjugates. Curr. Opin. Struct. Biol. 6, 692.
23. (a) Ardoin, N., and Astruc, D. (1995) Molecular trees-from syntheses towards applications. Bull. Soc. Chim. Fr., 875.
24. (b) Issberner, J., Moors, R., and Vögtle, F. (1994) Dendrimers: from generations and functional groups to functions. Angew. Chem., Int. Ed. Engl. 33, 2413.
25. (c) Fréchet, J. M. J. (1994) Functional polymers and dendrimers: reactivity, molecular architecture, and interfacial energy. Science 263, 1710 and references cited therein.
26. (a) Wong, C.-H., Halcomb, R. L., Ichikawa, Y., and Kajimoto, T. (1995) Enzymes in organic synthesis: application to the problems of carbohydrate recognition (part 1). Angew. Chem., Int. Ed. Engl. 34, 412.
27. (b) Wong, C.-H., Halcomb, R. L., Ichikawa, Y., and Kajimoto, T. (1995) Enzymes in organic synthesis: application to the problems of carbohydrate recognition (part 2). Angew. Chem., Int. Ed. Engl. 34, 521.
28. Zanini, D., Park, W. K. C., and Roy, R. (1995) Synthesis of novel dendritic glycosides. Tetrahedron Lett. 36, 7383.
29. Unverzagt, C., Kunz, H., and Paulson, J. C. (1990) High efficiency synthesis of sialyloligosaccharides and sialoglycopeptides. J. Am. Chem. Soc. 112, 9308.
30. Lee, Y. C., and Lee, R. T. (1974) Synthesis of 3-(2-aminoethylthio)propyl glycosides. Carbohydr. Res. 37, 193.
31. Park, W. K. C. (1995) Design and synthesis of GM3-and lactose-containing multivalent conjugates. Ph.D. Thesis, University of Ottawa, Ottawa, ON.
32. Gottschalk, A., and Bhargava, A. S. (1972) in Glymproteins: Their Composition, Structure and Function (A. Gottschalk, Ed.) pp 821-829, Elsevier Publishing Co., New York.
33. Goldstein, I. J., and Poretz, R. D. (1986) Isolation, Physicochemical Characterization, and Carbohydrate-Binding Specificity of Lectins. In The Lectins Properties, Functions, and Applications in Biology and Medicine (I. E. Liener, N. Sharon, and I. J. Goldstein, Eds.) pp 103-115, Academic Press, Inc., Orlando.
34. Goldstein, I. J. and Poretz, R. D. (1986) Isolation, Physicochemical Characterization, and Carbohydrate-Binding Specificity of Lectins. In The Lectins Properties, Functions, and Applications in Biology and Medicine (I. E. Liener, N. Sharon, and I. J. Goldstein, Eds.) pp 160-163, Academic Press, Inc., Orlando.
35. Bhattacharyya, L., Haraldsson, M., Sharon, N., Lis, H., and Brewer F. (1989) Binding and precipitating activities of Erythrina lectins with complex type carbohydrates and synthetic cluster glycosides. A comparative study of the lectins from E. Coralludendron, E. Cristagalli, E. Flabelliformis, and E. Indica. Glycoconjugate J. 6, 141.