Synthesis of sialyl- and sulfo-Lex/Lea analogs containing N-alkyl-1-deoxynojirimycin as potential selectin blockers

Journal of Carbohydrate Chemistry

Volumn 20, Issue 9, 2001, Pages 789-812

  Furui, Hiroyasu ^a,b   Ando Furui, Keiko ^a   Inagaki, Haruko ^a   Ando, Takayuki ^a   Ishida, Hideharu ^a   Kiso, Makoto ^a  

^a GIFU UNIVERSITY   (Japan)

^b KAGOME CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035527839     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108657     Document Type: Article

References (27)

1. Synthetic Studies on Sialoglycoconjugates, Part 122. For Part 121, see Ando, T.; Ishida, H.; Kiso, M. A highly efficient synthetic route to α(2→3)/α(2→6) disialyl Lewis a as a cancer associated carbohydrate antigen. J. Carbohydr. Chem. 2001, 20, in press.
2. Synthetic Studies on Sialoglycoconjugates, Part 122. For Part 121, see Ando, T.; Ishida, H.; Kiso, M. A highly efficient synthetic route to α(2→3)/α(2→6) disialyl Lewis a as a cancer associated carbohydrate antigen. J. Carbohydr. Chem. 2001, 20, in press.
3. a antigen. J. Biol. Chem. 1985, 260, 9388-9392.
4. Fukushima, K.; Hirota, M.; Terasaki, P.; Wakisaka, A.; Togashi, H.; Chia, D.; Suyama, N.; Fukushi, Y.; Nudelman, E.; Hakomori, S. Characterization of sialosylated Lewis X as a new tumor-associated antigen. Cancer Res. 1984, 44, 5279-5285.
5. Varki, A. Selectin ligands. Proc. Natl. Acad. Sci. USA 1994, 91, 7390-7397.
6. Kannagi, R. Carbohydrate-mediated cell adhesion involved in hematogenous metastasis of cancer. Glycoconjugate J. 1997, 14, 577-584.
7. Nakamori, S.; Furukawa, H.; Hiratsuka, M.; Iwanaga, T.; Imaoka, S.; Ishikawa, O.; Kabuto, T.; Sasaki, Y.; Kameyama, M.; Ishiguro, S.; Irimura, T. Expression of carbohydrate antigen sialyl Le(a): a new functional prognostic factor in gastric cancer. J. Clin. Oncol. 1997, 15, 816-825.
8. Sawada, N.; Ito, M.; Ishida, H.; Kiso, M. The first synthesis of glycan parts of lacto-ganglio- and neolactoganglio-series gangliosides. Tetrahedron Lett. 2001, 42, 1745-1747.
9. Komba, S.: Yamaguchi, M.; Ishida, H.; Kiso, M. 6-0-Sulfo de-N-acetylsialyl Lewis x as a novel high-affinity ligand for human L-selectin: Total synthesis and structural characterization. Biol. Chem. 2001, 382, 233-240.
10. Kameyama, A.; Ishida, H.; Kiso, M.; Hasegawa, A. Synthetic Studies on Sialoglyco-conjugates 22:Total synthesis of tumor-associated ganglioside, sialyl Lewis X. J. Carbohydr. Chem. 1991, 10, 549-560.
11. a. J. Carbohydr. Chem. 1994, 13, 641-654.
12. Hasegawa, A.; Kiso, M. Synthesis of sialyl Lewis X ganglioside and analogs. Methods Enzymol. 1994, 242, 158-173.
13. Ikami, T.; Ishida, H.; Kiso, M. Synthesis and biological activity of glycolipids, with a focus on gangliosides and sulfatide analogs. Methods Enzymol. 2000, 311, 547-568.
14. a epitopes recognized by selectins. Bioorg. Med. Chem. 1994, 2, 1295-1308.
15. Kiso, M.; Furui, H.; Ishida, H.; Hasegawa, A. Studies on selectin binding inhibitors: Synthesis of sialyl-Lewis X and sialyl-Lewis A epitope analogs containing 2-acetamido derivative of N-methyl-1-deoxynojirimycin. J. Carbohydr. Chem. 1996, 15, 1-14.
16. Ogawa, H.; Harada, Y.; Kyotani, Y.; Ueda, T.; Kitazawa, S.; Kandori, K.; Seto, T.; Ishiyama, K.; Kojima, M.; Ohgi, T.; Ezure, Y.; Kise, M. An efficient synthesis of sulfo Lewis x analog containing 1-deoxynojirimycin. J. Carbohydr. Chem. 1998, 17, 729-738.
17. Hasegawa, A.; Kiso, M. Design and synthesis of cell adhesion carbohydrate ligands/inhibitors. In Carbohydrates in Drug Design; Witczak, Z. J.; Nieforth, K. A. Eds.; Marcel Dekker, Inc.; New York, 1997; 137-155.
18. Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivasatava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Structure-function studies on selectin carbohydrate ligands. Modification to fucose, sialic acid and sulphate as a sialic acid replacement. Glycobiology 1993, 3, 633-639.
19. Yuen, C.-T.; Bezouska, K.; O'Brien, J.; Stoll, M.; Lemonie, R.; Lubineau, A.; Kiso, M.; Hasegawa, A.; Bockovich, J.; Nicolaou, K. C.; Feizi, T. Sulfated blood group Lewis a, a superior oligosaccharide ligand for human E-selectin. J. Biol. Chem. 1994, 269, 1595-1598.
20. Yoshida, M.; Suzuki, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Synthetic studies on sialoglycoconjugates 81:Synthesis of positional isomers of sialyl Lewis X epitope containing 1-deoxy-D-glucose in place of N-acetylglucosamine, and their inhibitory activity to selectin-mediated adhesion. J. Carbohydr. Chem. 1996, 15(2), 147-162.
21. Tanahashi, E.; Murase, K.; Shibuya, M.; Igarashi, Y.; Ishida, H.; Hasegawa, A.; Kiso, M. Synthetic studies on selectin ligands/inhibitors: A systematic synthesis of sulfatide and its higher congeners carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute. J. Carbohydr. Chem. 1997, 16(6), 831-858.
22. Kiso, M.; Katagiri, H.; Furui, H.; Hasegawa, A. Studies on 1-deoxynojirimycin-containing glycans: Synthesis of novel disaccharides related to lactose, lactosamine, and chitobiose. J. Carbohydr. Chem. 1992, 11, 627-644.
23. Kiso, M.; Ando, K.; Inagaki, H.; Ishida, H.; Hasegawa, A. Synthetic and structural studies of α-sialyl-(2→6) and α-sialyl-(2→3) 1-deoxynojirimycin derivatives potentially useful for biomedical applications. Carbohydr. Res. 1995, 272, 159-178.
24. Simanek, E. E.; McGarver, G. J.; Jablonowski, J. A.; Wong, C.-H. Selectin-carbohydrate interactions: from natural ligands to designed mimics. Chem. Rev. 1998, 98, 833-862.
25. Wada, Y.; Saito, T.; Matsuda, N.; Ohmoto, H.; Yoshino, K.; Ohashi, M.; Kondo, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Studies on selectin blockers. 2. Novel selectin blocker as potential therapeutics for inflammatory disorders. J. Med. Chem. 1996, 39, 2055-2059.
26. Tsukida, T.; Moriyama, H.; Kurokawa, K.; Achiha, T.; Inoue, Y.; Kondo, H. Studies on selectin blockers. 7. Structure-activity relationships of sialyl Lewis x mimetics based on modified Ser-Glu dipeptides. J. Med. Chem. 1998, 41, 4279-4287, and references therein.
27. Garegg, P. J.; Oscarson, S. A synthesis of 8-methoxycarbonyloct-1-yl O-α-D-galac-topyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)- 2-acetamido-2-deoxy-β-D-glucopyranoside. Carbohydr. Res. 1985, 136, 207-213.