α-Gal oligosaccharides: Chemistry and potential biomedical application

Current Medicinal Chemistry

Volumn 6, Issue 2, 1999, Pages 155-164

  Janczuk, A ^a   Li, J ^a   Zhang, W ^a   Chen, X ^a   Chen, Y ^a   Fang, J ^a   Wang, J ^a   Wang, P G ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GAL OLIGOSACCHARIDE; INTEGRIN; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

CARBOHYDRATE ANALYSIS; CELL SURVIVAL; CONFORMATION; GRAFT REJECTION; IMMUNOTHERAPY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW; SYNTHESIS; XENOTRANSPLANTATION;

ANIMALS; ANTIGENS, HETEROPHILE; CARBOHYDRATE SEQUENCE; DISACCHARIDES; GALACTOSYLTRANSFERASES; GRAFT REJECTION; HUMANS; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; TRANSPLANTATION, HETEROLOGOUS;

EID: 0032980782     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (90)

1. (a) Platt, J. L. Nature 1998, 392, 11 (Supp).
2. (b) Rother R. P.; Squito, S. P. Cell 1996, 36, 185.
3. (c) Cooper, D.K.C.; Koren, E.; Oriol, R. Immunol. Rev. 1994, 141, 31.
4. (d) Galili, U. Immunol. Today 1993, 14, 480.
5. (e) Sandrin, M. S.; Vaughan, H. A.; McKenzie, I. F. C. Transplant. Rev. 1994, 8, 134.
6. (f) Samuelsson, B. E.; Rydberg, L.; Breimer, M. E.; Backer, A.; Gustavsson, M.; Holgersson, J.; Karlsson, E.; Uyterwaal, A. -C.; Cairns, T.; Welsh, K. Immunol. Rev. 1994, 141, 151.
7. (a) Cooper, D.K.C.; Koren, E.; Oriol, R. Immunol. Rev. 1994, 141, 31.
8. (b) Galili, U. Immunol. Today 1993, 14, 480.
9. (c) Sandrin, M. S.; Vaughan, H. A.; McKenzie, I. F. C. Transplant. Rev. 1994, 8, 134.
10. (d) Samuelsson, B. E.; Rydberg, L.; Breimer, M. E.; Backer, A.; Gustavsson, M.; Holgersson, J.; Karlsson, E.; Uyterwaal, A. -C.; Cairns, T.; Welsh, K. Immunol. Rev. 1994, 141, 151.
11. Rieben, R.; Von Allmen, E.; Korchagina, E.; Nydegger, U.; Neethling, F. A.; Kujundzic, M.; Koren, E.; Bovin, N.; Cooper, D. K. C. Xenotransplantation 1995, 2, 98.
12. (a) Taniguchi, S.; Neethling, F.A.; Korchagina, E.Y.; Bovin, N.; Ye, Y.; Kobayashi, T.; Niekrasz M.; Li, S.; Koren, E.; et al. Transplant 1996, 62(10), 1379-1384.
13. (b) Jaison, Paliakkara L.; Appukuttan, P.S., Indian J. Biochem. Biophys. 1992, 29(3), 266-270.
14. (a) Neethling, F.; Koren, E.; Ye, Y.; Richars, S.; Kujundzic, M.; Oriol, R.; Cooper, D. Transplant 1994, 57(6), 959-963.
15. (b) Nagasaka, T.; Kobayashi, T.; Muramastu, H.; Fujimoto, H.; Muramastu, T.; Takagi, H. Biochem. Biophys. Res. Commun. 1997, 232, 731-736.
16. (a) Lussow, A.R.; Buelow, R.; Pouletty, P. U.S. Patent 5,714,332.
17. (b) Wang, P.G. NIH Proposal.
18. (a) Nilsson, K. G. I. Modern Methods in Carbohydrate Synthesis, Khan, S.H.; O'Neill, R. A. Eds.; Harwood Acedemic Publisher: The Netheralands, 1996, pp518-547
19. (b) Fernandez-Mayorals, A. Top. Curr. Chem. 1997, 186,1.
20. (c) Murata, T.; Usui, T. Biosci. Biotech. 1997, 61, 1059.
21. (d) Crout, D.H. G.; Vic, G. Curr. Opin. Chem. Bio. 1998, 2, 98.
22. (a) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133.
23. (b) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 169.
24. (c) Vic, G.; Scigelova, M.; Hastings, J. J.; Howarth, O. W.; Crout, D. H. G. Chem. Commun. 1996, 1473.
25. (d) Mstsuo, I.; Fujimoto, H.; Isomura, M.; Ajisaka, K. Bioorg. Med. Chem. Lett. 1997, 7, 255.
26. Beyer, A. T.; Sadler, J. E.; Rearick, J. I.; Paulson, J. C.; Hill, R. L. Adv. Enzymol. 1981, 52, 24.
27. (a) Joziasse, D. H.; Shaper, J. H.; Eijnden, D. H.; Tunen, A. J. V.; Shaper, N. L. J. Biol.Chem. 1989, 264, 14290.
28. (b) Joziasse, D. H.; Shaper, N. L.; Salyer, L. S.; Eijnden, D. H.; Spoel, A. C.; Shaper, J. H. Eur. J. Biochem. 1990, 191, 75.
29. (c) Larsen, R. D.; Pajan, V. P.; Ruff, M. M.; Kukowska-Latallo, J.; Cummings, R. D.; Lowe, J. B. Proc. Natl. Acad. Sci. USA 1989, 86, 8227.
30. (d) Joziasse, D. H.; Shaper, N. L.; Kim, D.; Eijnden, D. H.; Shaper, J. H. J. Biol. Chem. 1992, 267, 5534.
31. (e) Strahan, K. M.; Gu, F.; Preece. A. F.; Gustavsson, I.; Andersson, L.; Gustafsson, K. Immunogenetics 1995, 41, 101.
32. (f) Henion, T. R.; Macher, B. A.; Anaraki, F.; Galili, U. Glycobiology 1994, 4, 193.
33. Fang, J.; Li, J.; Chen, X.; Zhang, Y.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc 1998, 120, 6635.
34. Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167.
35. Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618.
36. Hokke, C. H.; Zervosen, A.; Elling, L.; Joziasse, D. H.; Van Den Eijnden, D. H. Glycoconjugate Journal 1996, 13, 687.
37. (a) Wong, C. -H.; Haynie, S. L.; Whitesides, G. M. J. Org. Chem. 1982, 47, 5416.
38. (b) Auge, C.; Mathieu, C.; Merienne, C. Carbohydr. Res. 1986, 151, 147.
39. (c) Thiem, J.; Wiemann, T. Synthesis 1992, 141.
40. (d) Wong, C. -H.; Wang, R.; Ichihawa, Y. J. Org. Chem. 1992, 57, 4343.
41. (e) Zervosen, A.; Elling, L. J. Am. Chem. Soc. 1996, 118, 1836.
42. Abbas, S.; Matta, K. L. Carbohydr. Res. 1983, 123, 53.
43. Kunz, H.; Dombo, B. Angew. Chem. Int. Ed. Engl. 1988, 27, 711.
44. Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692.
45. (a) Jacquinet, J. -C.; Duchet, D.; Milat, M. -L.; Sinay, P. J. Chem. Soc. Perkin. I. 1981, 326.
46. (b) Koike, K.; Sugimoto, M.; Sato, S.; Ito, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1987, 163, 189.
47. (c) Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061.
48. (d) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67.
49. (e) Zhu, T.; Boons, G.-J. J. Chem. Soc. Perkin Trans. 1, 1998, 857.
50. Neethling, F.; Joziasse, D.; Bovin, N.; Cooper, D. K. C.; Oriol, R. Transplant. Int. 1996, 9, 98.
51. (a) Bock, K. Pure Appl. Chem., 1983, 55, 605.
52. (b) Cumming, D. A.; Carver, J. P. Biochemistry 1987, 26, 6676.
53. (c) Lemieux, R. U. Chem. Soc. Rev. 1989, 18, 347.
54. (d) Homans, S. W. Progr. NMR Spectrosc., 1990, 22, 55.
55. (e) Meyer, B. Top. Curr. Chem. 1990, 154, 141.
56. (f) Bush, C. A.; Cagas, P. in Advances in Biophysical Chemistry, Bush, C. A. Eds.; JAI Press, Greenwich, Connecticut 1992; p 149.
57. (g) Walker, S.; Murnick, J. Kahne, D. J. Am. Chem. Soc. 1993, 115, 7954.
58. (h) Peters, T.; Pinto, B. M. Curr. Opin. Strut. Biol., 1996, 6, 710.
59. (i) Poveda, A.; Jimenez-Barbero, J. Chem. Soc. Rev. 1998, 27, 133.
60. Piantinis, U.; Sorensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 104, 6800.
61. Braunschweiler, L.; Ernst, R. R. J. Magn. Reson. 1983, 53, 521.
62. Kessler, H.; Oschkinat, H.; Griesinger, C. J. Magn. Reson. 1986, 70, 106.
63. (a) Bax, A. J. Magn. Reson. 1984, 57, 314.
64. (b) Bax, A.; Ferretti, J. A.; Nashed, N.; Jerina, D. M. J. Org. Chem. 1985, 50, 3029.
65. (a) Muller, L. J. Am. Chem. Soc. 1979, 101, 4481.
66. (b) Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565.
67. (c) Cassels, F. J.; Fales, H. M.; London, J.; Carlson, R. W.; van Halbeek, H. J. Biol. Chem. 1990, 265, 14127.
68. (a) Haasnoot, C. A. G.; De Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
69. (b) Altona, C.; Hasnoot, C. A. G. Magn. Reson. Chem. 1980, 13, 417
70. (a) Ladam, P.; Gharbi-Benarous, J.; Piotto, M.; Delaforge, M.; Girault, J. P. Magn. Reson. Chem. 1994, 32, 1.
71. (b) Hricovíni, M.; Tvaroska, I.; Uhrin, D.; Batta, G. Y. J. Carbohydr. Chem. 1989, 8, 389.
72. (c) Jippo, T.; Kamo, O.; Nagayama, K. J. Magn. Reson. 1986, 66, 344.
73. Tvaroska, I.; Taravel, F. R. Adv. Carbohydr. Chem. Biochem. 1995, 51, 15.
74. Hricovini, M.; Tvaroska, I.; Hirsch, J. Carbohydr. Res. 1990, 198, 193.
75. (a) Von der Lieth, C.-W.; Kozar, T.; Hull, W. E. J. Mol. Struct. 1997, 395, 225.
76. (b) Woods, R. J. Glycoconjugate J. 1998, 15, 209.
77. Stuike-Prill, R.; Meyer, B. Eur. J. Biochem. 1990, 194, 903.
78. Peters, T.; Meyer, B.; Stuike-Prill, R.; Somorjai, R.; Brisson, J.-R. Carbohydr. Res. 1993, 238, 73.
79. (a) Junghemi, L.N.; Shepherd, T.A. Chem. Rev 1994, 94, 1553-1566
80. (b) Koppel, G.A. Bioconj. Chem. 1990, 1, 13.
81. Varner, J. A; Cheresha, D. A. Curr. Opin. Cell Biol. 1996, 8,724-730.
82. Hynes, R. O. Cell 1992, 69, 11-25.
83. Varner, J. A; Cheresha, D. A. Curr. Opin. Cell Biol. 1996, 8,724-730
84. (a) Brooks P.C.; Montgomery A.M.P.; rosenfeld M.; Reisfeld, R. A.; Hu, T.; Klier, G.; Cheresh, D. Cell 1994, 79, 1157-1164.
85. (b) Brooks, P.C.; Stromblad, S.; Klemke, R.; Visscher, D. J. Clin. Invest. 1995, 96, 1815-1822.
86. (c) Montgomery, A.M.P.; Reisfeld, R.A; Cheresh, D. A. Proc. Natl. Acad. Sci., USA 1994, 91, 8856-8860.
87. Clark, E.A; Brugge, J.S. Science 1995, 268, 233-239.
88. (a) Trikha, M.; Timar J.; Lundy S.; Szekeres, K.; Grignon D.; Poster A.T; Honn, K.V. Cancer Res. 1997, 57, 2522-2528.
89. Pasqualini, R.; Koivunen, E.; Ruoslahti, E. Nature Biotech 1997, 15, 542-546.
90. Arap, W.; Pasqualini, R.; Ruoslahti, E. Science 1998, 279, 377-380.