Crystal and molecular structure of a histo-blood group antigen involved in cell adhesion: The Lewis x trisaccharide

Glycobiology

Volumn 6, Issue 5, 1996, Pages 537-542

  Pérez, Serge ^a   Mouhous Riou, Nadine ^a   Nifant'ev, Nikolay E ^b   Tsvetkov, Yury E ^b   Bachet, Bernard ^c   Imberty, Anne ^d  

^a CEMAGREF   (France)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c UNIVERSITÉ PIERRE ET MARIE CURIE   (France)

^d CNRS   (France)

Author keywords

Carbohydrate carbohydrate interactions; Cell adhesion; Histo blood group; Lewis x; Trisaccharide

Indexed keywords

ANTIGEN; TRISACCHARIDE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CELL ADHESION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HUMAN; HUMAN CELL; NORMAL HUMAN; PRIORITY JOURNAL;

EID: 0029801233     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/6.5.537     Document Type: Article

References (33)

1. N2 substitution. Carbohydr. Res., 201, 69-77.
2. Aspinall, G.O., Monteiro, M.A., Pang, H., Walsh, E.J. and Moran, A.P. (1994) O antigen chains in the lipopolysaccharide of H.pylori. Carbohydr. Lett., 1, 151-156
3. Bird, J.M. and Kimber, S.J. (1984) Oligosaccharides containing fucose linked α(1-3) and α(1-4) to N-acetylglucosmaine cause decompaction of mouse morulae. Dev. Biol., 104, 449-460.
4. Biswas, M. and Rao, V.S.R. (1980) Conformational studies on the ABH and Lewis blood group oligosaccharides. Biopolymers, 19, 1555-1565.
5. Clausen, H. and Hakomori, S.-I. (1989) ABH and related histo-blood group antigens: immunochemical differences in carrier isotypes and their distribution. Vox. Sang., 56, 1-20.
6. Dean, B., Oguchi, H., Cai, S., Otsuji, E., Tasgiro, K. Hakomori, S.-i. and Toyokuniu, T. (1993) Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors. Carbohydr. Res., 245, 175-192.
7. Eggens, J., Fenderson, B., Toyokuni, T., Dean, B., Stroud, M. and Hakamori, S. (1989) Specific interaction between Lex and Lex determinants. A possible basis for cell recogniaon in preimplantation embryos and in embryonal carcinoma cells. J. Biol Chem , 264, 9476-9484.
8. Feizi, T. (1985) Demonstration by monoclonal antibodies that carbohydrate structures of glycoproteins and glycolipids are onco-developmental antigens. Nature, 314, 53-57.
9. Fenderson, B., Zehavi, U. and Hakomori, S. (1984) A multivalent lacto-N-fuco pentaose III-lysyllysine conjugate decompacts preimplantation mouse embryos, while the free oligosaccharide is ineffective. J. Exp. Med., 160, 1591-1596.
10. Hakomori, S. (1989) Aberrant glycosylation in tumors and tumor-associated carbohydrate antigens. Adv. Cancer Res. 52, 257-331.
11. Hakomori, S.-I., Nudelman, E., Levery, S., Solter, D. and Knowles, B.B (1981) The hapten structure of a developmentally regulated glycolipid antigen (SSEA-1) isolated from human erythrocytes and adenocarcinoma. Biochem. Biophys. Res. Commun., 100, 1578-1586.
12. Henry, S., Oriol, R. and Samuelsson, B. (1995) Lewis-histo-blood group system and associated secretory phenotypes. Vox Sang., 69, 166-182.
13. Ichikawa, Y., Lin, Y.-C., Dumas, D.P., Shen, G.-J., Garcia-Junceda, E., Williams, M.A., Bayer, R., Ketcham, C., Walker, L.E., Paulson, J.C. and Wong, C.-H. (1992) Chemical-enzymatic synthesis and conformational analysis of sialyl Lewis x and derivatives. J. Am. Chem. Soc. 114, 9283-9298.
14. Imberty, A., Mikros, E., Koca, J., Mollicone, R., Oriol, R. and Pérez, S. (1995) Computer simulation of histo-blood group oligosaccharides energy maps of all constituting disaccharides and potential energy surfaces of 14 ABH and Lewis carbohydrate antigens. Glycoconj. J., 12, 331-349.
15. International Tables for X-Ray Crystallography (1974) Vol. 4. Kyoch Press, Birmingham.
16. Jeffrey, G A. and Saenger, W. (1991) Hydrogen Bonding in Biological Structures. Springer-Verlag, Berlin.
17. x expression. Glycoconj. J., 11, 238-248.
18. Lasky, L.A. (1992) Selectins: interpreters of cell-specific carbohydrate information during inflammation Science, 258, 964-969.
19. Lemieux, R.U. Bock, K., Delbaere, L.T.J., Koto, S. and Rao, V.S. (1980) The conformations of oligosaccharides related to the ABH and Lewis human blood group determinants. Can. J. Chem., 58, 631-653.
20. Miller, K.E., Mukhopadhyay, C., Cagas, P. and Bush, C.A. (1992) Solution structure of the Lewis x oligosaccharide determined by NMR spectroscopy and molecular dynamics simulations. Biochemistry, 31, 6703-6709.
21. Nivant'ev, N.E., Backmowsky, L.V. and Kochetkov, N.K. (1988) Synthesis of derivatives of 2-amino-2-deoxy-4-O-(α and β-D-galactopyranosyl)-D-glucose. Carbohydr. Res., 174, 61-72.
22. Nivant'ev, N.E., Khatuntseva, E.A., Shashkov, A.S. and Bock, K. (1995) Carbohydr. Lett., 2, 399-406.
23. Ogawa, T., Beppu, K. and Nakabayashi, S. (1981) Trimethylsilyl trifluorometh-anesulfonate as an effective catalyst of glycoside synthesis. Carbohydr. Res., 93, c6-c9
24. Oriol, R. (1995) ABO, Hh, Lewis, and secretion. Serology, genetics, and tissue distribution. In Cartron, J.P. and Rouger, P. (eds.), Blood Cell Biochemistry, Vol. 6. Plenum, New York, pp. 161-171.
25. Pérez, S., Imberty, A. and Carver, J.P. (1994) Molecular modeling: an essential component in the structure determination of olgiosaccharides and polysaccharides. Adv. Comput. Biol., 1, 146-202
26. Pozsgay, V. and Jennings, H.J. (1987) A new method for the synthesis of O-glycosides from S-glycosides. J. Org. Chem., 52, 4635-4637.
27. Schwartz, D.E., Lee, H.H., Carver, J.P. and Krepinsky, J.J. (1985) Synthesis of model oligosaccharides of biological significance. 4. Synthesis of a fucosylated N,N′-diacetychitobioside and related oligosaccharides. Can. J. Chem. 63, 1073-1079.
28. Solter, D. and Knowles, B.B. (1978) Monoclonal antibodies defining a stage specific mouse embryonic antigen. Proc. Natl. Acad. Sci. USA, 75, 5565-5569.
29. Thogersen, H., Lemieux, R.U., Bock, K. and Meyer, B. (1982) Further justification for the exo-anomeric effect. Conformational analysis based on nuclear magnetic resonance spectroscopy of oligosaccharides. Can. J. Chem., 60, 44-57.
30. x as repeating unit. Eur. J. Biochem., 225, 467-482.
31. Varki, A. (1994) Selectin ligands. Proc. Natl. Acad. Sci. USA, 91, 7390-7397.
32. Velupillai, P. and Harn, D.A. (1994) Oligosaccharide specific induction of interleukin 10 production by B220+ cells from schistosome-infected mice: a mechanism for regulation of CD4+ T-cell subsets. Proc. Natl. Acad. Sci. USA, 91, 18-22.
33. Yvelin, F., Zhang, Y.-M., Mallet, J.M., Robert, F., Jeannin, Y. and Sinay, P. Carbohydr. Lett. 1, 475-482.