Large scale synthesis of linker-modified sialyl Lewis(X), Lewis(X) and N-acetyllactosamine

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6341-6358

  Kretzschmar, Gerhard ^a   Stahl, Wilhelm ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; GLYCOSYLTRANSFERASE; LACTOSE; N ACETYLLACTOSAMINE; OLIGOSACCHARIDE; SELECTIN ANTAGONIST; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; FUCOSYLATION; ISOLATION PROCEDURE; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; REACTION ANALYSIS; SIALYLATION; STRUCTURE ANALYSIS;

EID: 0032482294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00294-4     Document Type: Article

References (60)

1. 1. Reviews: a) Mousa, S.A., Drugs of the Future, 1996, 21, 283-289;
2. b) Watson, S.R., Adhes. Recept. Ther. Targets. 1996, 61-73, Ed.: Horten, M.A., CRC Press, BocaRaton/Fla.;
3. c) Fukuda, M., Bio. Med. Chem., 1995, 3, 207-215;
4. d) Springer, T.A., Cell, 1994, 76, 301-314.
5. 2. a) Kannagi, R., Glycoconjugate J., 1997, 14, 577-584;
6. b) Renkonen, R., Mattila, P., Majuri, M.-L., Räbinä, J., Toppila, S., Renkonen, J., Hirvas, L., Niittymäki, J., Turunen, J.P., Renkonen, O., Pavonen, T., Glycoconjugate J., 1997, 14, 593-600;
7. c) McEver, R.P., Glycoconjugate J., 1997, 14, 585-591.
8. X-propanolamine # 06-002, 1.0 mg price US$ 1195.
9. 4. a) Wong, C.-H., Halcomb, R.L., Ichikawa, Y., Kajimoto, T., Angew. Chem. Int. Ed. Engl, 1995, 34, 412-432;
10. b) Wong, C.-H., Halcomb, R.L., Ichikawa, Y., Kajimoto, T., Angew. Chem. Int. Ed. Engl, 1995, 34, 521-546;
11. c) 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.,Wong, C.-H., J. Am. Chem. Soc., 1992, 114, 9283-9298.
12. 5. a) Kuznik, G., Hörsch, B., Kretzschmar, G., Unverzagt, C., Bioorg. Med. Chem. Lett., 1997, 7, 577-580;
13. b) Kretzschmar, G., Tetrahedron, 1998, 54, 3765-3780.
14. 6. Kretzschmar, G., Sprengard, U., Kunz, H., Bartnik, E., Schmidt, W.D., Toepfer, A., Hörsch, B., Krause, M., Seiffge, D., Tetrahedron, 1995, 51, 13015-13030.
15. 7. Sprengard, U., Schudok, M., Schmidt, W.D., Kretzschmar, G, Kunz, H., Angew. Chem. Int. Ed. Engl. 1996, 35, 321-324.
16. 8. Ratcliffe, M.R., Venot, A.P., Abbas, Z.S., Chembiomed Ltd, EP 0319253, priority from 2/12/1987, filed 30/11/1988, published 7/6/1989 (US 127905).
17. 9. a) Nicolaou, K.C., Hummel, C.W., Bockovich, N.J., Wong, C.-H., J. Chem. Soc., Chem. Commun., 1991, 870-872;
18. b) Nicolaou, K.C., Hummel, C.W., Iwabuchi, Y., J. Am. Chem. Soc., 1992, 114, 3126-3128;
19. c) Nicolaou, K.C., Caulfield, T.J., Kataoka, H., Stylianides, N.A., J. Am. Chem. Soc., 1990, 112, 3693-3695.
20. 10. a) Hasegawa, A., Ando, T., Kameyama, A., Kiso, M., Carbohydr. Res., 1992, 230, C1-C5;
21. b) Hasegawa, A., Ando, T., Kameyama, A., Kiso, M., J. Carbohydr. Chem., 1992, 11, 645-658;
22. c) Kameyama, A., Ishida, H., Kiso, M., Hasegawa, A., J. Carbohydr. Chem., 1991, 10, 549-560.
23. X-Glycosphingolipide, Konstanzer Dissertationen 359, Hartung-Gorre Verlag, Konstanz, 1992.
24. 12. a) Danishefsky, S.J., Gervay, J., Peterson, J.M., McDonald, F.E., Koseki, K., Oriyama, T., Griffith; D.A., Wong, C.-H., Dumas, D.P., J. Am. Chem. Soc., 1992, 114, 8329-8331;
25. b) Danishefsky, S.J., Gervay, J., Peterson, J.M., McDonald, F.E., Koseki, K., Oriyama, T., Griffith, D.A., Marseden, S.P., J. Am. Chem. Soc., 1995, 117, 1940-1953.
26. 13. Kondo, H., Ichikawa, Y., Wong, J. Am. Chem. Soc., 1992, 114, 8748-8750.
27. 14. Dekany, G., Wright, K., Toth, I., J. Carbohydr. Chem., 1997, 16, 983-999.
28. 15. a) Kretzschmar, G., Toepfer, A., Hüls, C., Krause, M., Tetrahedron, 1997, 53, 2485-2494 and ref. cited herein;
29. 14 releases trace amounts of polyanions being the most potent P-selectin antagonists reported to date.
30. 16. Yamazaki, F., Kitajima, T., Numata, T., Ito, Y., Ogawa, T., Carbohydr. Res., 1990, 201, 15-24.
31. 17. a) Hasegawa, A., Ohki, H., Nagahama, T., Ishida, H., Kiso, M., Carbohydr. Res., 1991, 121, 277-281;
32. b) Hasegawa, A., Nagahama, T., Ohki, H., Hotta, K., Ishida, H., Kiso, M., J. Carbohydr. Chem., 1991, 10, 493-498.
33. 18. Banoub, J., Chem. Rev., 1992, 92, 1167-1195.
34. 19. Kiso, M., Nishigushi, H., Murase, S., Hasegawa, A., Carbohydr. Res., 1981, 88, C5-C8.
35. 20. Lemieux, R.U., Takeda, T., Chung, B.Y., ACS Symp. Ser., 1976, 39, 90-115.
36. 21. Compound 5b was used likewise to prepare 1b. In addition, the whole sequence was performed using the 6-azidohexanol linker.
37. 22. a) Alais, J., Veyrieres, Carbohydr. Res., 1990, 207, 11-31;
38. b) Guilbert, B., Flitsch, S.L., J. Chem. Soc., Perkin Trans. I, 1994, 1181-1186.
39. 23. Paulsen, H., Paal, M., Carbohydr. Res., 1984, 135, 53-69.
40. 24. Chaplin, D., Crout, D.H.G., Bornemann, S., Hutchinson, Khan, R., J. Chem. Soc. Perkin Trans. I, 1992, 235-237.
41. 25. Sowell, C.G., Livesay, M.T., Johnson, D.A., Tetrahedron Lett., 1996, 37, 609-610.
42. 26. Fügedi, P., Garegg, P.J., Carbohydr. Res., 1986, 149, C9-C12.
43. 27. a) Garegg, P.J., Hultberg, H., Carbohydr. Res., 1981, 93, C10;
44. b) Garegg, P.J., Hultberg, H., Wallin, S., Carbohydr. Res., 1982, 108, 97;
45. c) Garegg, P.J., Classon, B., J. Carbohydr. Chem., 1989, 8, 5543-5551.
46. 28. a) Sprengard, U. Diplomarbeit, September 1993, Mainz/Germany;
47. b) Stahl, W., Sprengard, U., Kretzschmar, G., Kunz, H., Angew. Chem. Int. Ed. Engl., 1994, 33, 2096-2098;
48. c) Stahl, W., Sprengard, U., Kretzschmar, G., Schmidt, D.W., Kunz, H, J. Prakt. Chem., 1995, 337, 441-445.
49. 29. a) Numata, M., Sugimoto, M., Koike, K., Ogawa, T., Carbohydr. Res., 1987, 163, 209;
50. b) Gervay, J., Peterson, J.M., Oriyama, T., Danishefsky, S.J., J. Org. Chem., 1993, 58, 5465-5468;
51. c) Ray, A.K., Nielsson, U., Magnusson, G., J. Am. Chem. Soc., 1992, 114, 2256-2257.
52. 30. Martin, T.J., Brescello, R., Toepfer, A., Schmidt, R.R., Glycoconjugate J., 1993, 10, 16-25;
53. b) Kondo, H., Aoki, S., Ichikawa, Y., Halcomb, R.L., Ritzen, H., Wong, C.-H., J Org. Chem., 1994, 59, 864-877;
54. c) Sim, M.M., Kondo, H., Wong, C.-H., J. Am. Chem. Soc., 1993, 115, 2260-67.
55. 31. Alais, J., Veyrieres, A., Carbohydr. Res., 1981, 93, 164-165;
56. b) Jezo, I., Zemek, J., Chem. Zvesti, 1979, 33, 533-541.
57. 32. Tsukida, T., Yoshida, M., Kurokawa, K., Nakai, Y., Achiha, T., Kiyoi, T., Kondo, H., J. Org. Chem., 1997, 62, 6876-6881.
58. 33. Nashed, M.A., Musser, J.H., Carbohydr. Res., 1993, 250, C1-C4;
59. b) Singh, K., Fernandez-Mayoralas, A., Martin-lomas, M., J. Chem. Soc., Chem. Commun., 1994, 775-776.
60. 34. Hörsch, B., Ahlers, M., Kretzschmar, G., Bartnik, E., Seiffge, D., WO 9534-673, filed 16/06/1994.