A convenient and efficient synthesis of SLeX analogs

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 2938-2945

  Hayashi, Masaji ^a   Tanaka, Masashi ^a   Itoh, Masanori ^a   Miyauchi, Hiroshi ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; GLYCOSIDE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CELL ADHESION; CELL STRAIN HL 60; HUMAN; HUMAN CELL; REACTION ANALYSIS;

EID: 0029996792     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960125f     Document Type: Article

References (45)

1. (a) Phillips, M. L.; Nudeman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130.
2. (b) Walz, G.; Aruffo, A.; Kolanus, W,; Bevilacqua, M.; Seed, B. Science 1990, 250, 1132.
3. (c) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, E. M. Cell 1990, 63, 475.
4. (d) Tiemyer, M.; Swiedler, S. J.; Ishihara, M.; Moreland, M.; Schweingruber, H.; Hirtzer, P.; Brandley, B. K. Proc. Natl. Acad. Sci U.S.A. 1991, 88, 1138.
5. (a) Polley, M. J.; Phillips, M. L.; Wayner, E.; Nudeman, E.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224.
6. (b) Zhou, Q.; Moore, K. L.; Smith, D. F.; Varki, A.; McEver, R.; Cummings, R. D. J. Cell. Biol. 1991, 115, 557.
7. (a) Paulson, J. C. In Adhesion: its role in inflammatory disease; Harlan, J., Liu, D., Eds.; W. H. Freeman: New York, 1992; Chapter 2, p 19.
8. (b) Bevilapua, M. P.; Nelson, R. M. J. Clin. Invest. 1993, 91, 379.
9. (c) Springer, T. A. Cell 1994, 76, 301 and reference therein.
10. (a) Butcher, E. C. Cell 1991, 67, 1033.
11. (b) Shimizu, Y.; Newman, W.; Tanaka, Y.; Shaw, S. Immunol. Today 1992, 13, 106.
12. Pytela, R.; Pierschbacher, M. D.; Ginsberg, M. H.; Plow, E. F; Ruoslahti, E. Science 1986, 231, 1559.
13. In preliminary in vivo studies, adminstration of SLeX showed a marked thrapeutic effect on P-selectin-dependent induced lung injuries (Mulligan, M. S.; Paulson, J. C.; DeFrees, S. A.; Zeng, Z.-L.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149) and on selectin-dependent myocardial reperfusion injuries (Buerke, M.; Weyrich, A. S.; Zheng, Z.; Gaeta, F. C. A.; Forest, M. J.; Lefer, A. M. J. Clin. Invest. 1994, 93, 1140).
14. In preliminary in vivo studies, adminstration of SLeX showed a marked thrapeutic effect on P-selectin-dependent induced lung injuries (Mulligan, M. S.; Paulson, J. C.; DeFrees, S. A.; Zeng, Z.-L.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149) and on selectin-dependent myocardial reperfusion injuries (Buerke, M.; Weyrich, A. S.; Zheng, Z.; Gaeta, F. C. A.; Forest, M. J.; Lefer, A. M. J. Clin. Invest. 1994, 93, 1140).
15. Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096.
16. Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivasatava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633.
17. (a) Tyrrell, D.; James, P.; Rao, N., Foxall, C.; Abbas, S.; Dasgupta, F.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372.
18. (b) DeFrees, S. A., Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549.
19. Nelson, R. M.; Dolich, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin Invest. 1993, 91, 1157.
20. 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.; Wong, C.-H. J. Am. Chem Soc. 1992, 114, 9283.
21. Purchased from Sigma Chemical Co.
22. Wen, D. X.; Livinigston, B. D.; Medrihdszky, K. F.; Kelm, S.; Burlingame, A. L.; Paulson, J. C. J. Biol. Chem. 1992, 267, 21011.
23. (a) Vann, W. F.; Silver, R. P.; Abeijon, C.; Chang, K.; Aaronson, W.; Sutton, A.; Finn, C. W.; Lindner, W.; Kotsatos, M. J. Biol. Chem. 1987, 262, 17556.
24. (b) Shames, S. L.; Simon, E. S.; Christpher, C. W.; Schmid, W.; Whitesides, G. M.; Yang, L.-L. Glycobiology 1991, 1, 187.
25. (a) Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G. J. Org. Chem. 1988, 53, 5629.
26. (b) Jansson, K.; Noori, G.; Magnusson, G. J. Org. Chem. 1990, 55, 3181.
27. Boullanger, P.; Banoub, J.; Descotes, G. Can. J. Chem. 1987, 65, 1343,
28. DeFrees, S. A. et al. have already found that allyloxycarbonyl group on the amino group of glucosamine derivatives does not interfere with enzymatic galactosylation (private communication).
29. Unverzagt, C.; Kunz, H.; Paulson, J. C. J. Am. Chem. Soc. 1990, 112, 9308.
30. For reviews of substrate specificity for GalT, see: (a) Wong, C.-H.; Ichikawa, Y.; Krach, T.; Narvor, C. G.-L.; Dumas, D. P.; Look, G. C. J. Am. Chem. Soc. 1991, 113, 8137. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
31. For reviews of substrate specificity for GalT, see: (a) Wong, C.-H.; Ichikawa, Y.; Krach, T.; Narvor, C. G.-L.; Dumas, D. P.; Look, G. C. J. Am. Chem. Soc. 1991, 113, 8137. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
32. For reports on substrate specificities of 2,3-ST, see: (a) Kunz, H.; Harrews, A. Liebigs Ann. Chem. 1982, 41. (b) Schmidt, R. R.; Zimmreman, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (c) Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. (d) Ito Y.; Paulson, J. C. J. Am Chem. Soc. 1993, 115, 1603.
33. For reports on substrate specificities of 2,3-ST, see: (a) Kunz, H.; Harrews, A. Liebigs Ann. Chem. 1982, 41. (b) Schmidt, R. R.; Zimmreman, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (c) Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. (d) Ito Y.; Paulson, J. C. J. Am Chem. Soc. 1993, 115, 1603.
34. For reports on substrate specificities of 2,3-ST, see: (a) Kunz, H.; Harrews, A. Liebigs Ann. Chem. 1982, 41. (b) Schmidt, R. R.; Zimmreman, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (c) Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. (d) Ito Y.; Paulson, J. C. J. Am Chem. Soc. 1993, 115, 1603.
35. For reports on substrate specificities of 2,3-ST, see: (a) Kunz, H.; Harrews, A. Liebigs Ann. Chem. 1982, 41. (b) Schmidt, R. R.; Zimmreman, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (c) Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. (d) Ito Y.; Paulson, J. C. J. Am Chem. Soc. 1993, 115, 1603.
36. This three-step procedure was developed by Ratcliffe, R. M. (private communication). See also. DeFrees, S. A.; Gaeta, F. C. A.; Gaudino, J. J.; Zheng, Z.; Hayashi, M. Int. Pat. 1994, WO 9426760; Chem. Abstr., 1994.
37. This three-step procedure was developed by Ratcliffe, R. M. (private communication). See also. DeFrees, S. A.; Gaeta, F. C. A.; Gaudino, J. J.; Zheng, Z.; Hayashi, M. Int. Pat. 1994, WO 9426760; Chem. Abstr., 1994.
38. Ramphal, J. Y.; Hiroshige, M.; Lou, B.; Guadino, J.; Hayashi, M.; Chen, S. M.; Chiang, L. C.; Gaeta, F. C. A.; DeFrees, S. A. J. Med. Chem., in press.
39. Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1991, 15, 872.
40. Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
41. Lubineau, A , Gallic, J. L.; Malleron, A. Tetrahedron Lett. 1987, 28, 5041.
42. For the evaluation method of inhibition of HL-60 adhesion to recombinant soluble human E-selectin, see: DeFrees, S. A.; Kosch, W.; Way, W.; Paulson, J. C.; Sabesan, S.; Halcomb, R. L.; Huang, D.-H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 66.
43. DeFrees, S. A. Private communication. See also: DeFrees, S. A.; Phillips, L.; Zalipsky, S.; Guo, L. Submitted
44. DeFrees, S. A. Private communication. See also: DeFrees, S. A.; Phillips, L.; Zalipsky, S.; Guo, L. Submitted
45. Rice, K. G. In Neoglycoconjugates: Preparation and Applications; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; Chapter 9, pp 285-321.