Synthesis of 3e- and 6e-monosulfated and 3e,6e-disulfated lewis x pentasaccharides, candidate ligands for human l-selectin

Journal of Carbohydrate Chemistry

Volumn 19, Issue 2, 2000, Pages 151-169

  Lubineau, André ^a   Alais, Jocelyne ^a   Lemoine, Remy ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034360645     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328300008544072     Document Type: Article

References (44)

1. J.M. Harlan, D.Y. Liu, "Adhesion: its Role in Inflammatory Diseases"; H.H. Freeman, New York, 1992.
2. M.P. Bevilacqua and R.M. Nelson, J. Clin. Invest., 379 (1993).
3. E.L. Berg, M.K. Robinson, O. Manson, E.C. Butcher and J.L. Magnani, J. Biol. Chem., 266, 14869 (1991).
4. M. Larkin, T. Ahern, M.S. Stoll, M. Shaffer, D. Sako, J. O'Brien, C.T. Yuen, A.M. Larson, R.A. Childs, K.M. Barone, P.R. Langer-Safer, A. Hasegawa, M. Kiso, G.R. Larsen and T. Feizi, Biol. Chem., 267, 13661 (1992).
5. J.L. Magnani, Glycobiology, 1, 318 (1991)
6. C.T. Yuen, K. Bezouska, J. O'Brien, M. Stoll, R. Lemoine, A. Lubineau, M. Kiso, A. Hasegawa, N.J. Bockovich, K.C. Nicolaou and T. Feizi, J. Biol. Chem., 269, 1595 (1994).
7. P.J. Green, C.T. Yuen, R.A. Childs, W. Chai, M. Miyasaka, R. Lemoine, A. Lubineau, B. Smith, H. Ueno, K.C. Nicolaou and T. Feizi, Glycobiology, 5, 29 (1995)
8. J. Reignier, H. Sellak, R. Lemoine, A. Lubineau, G.M. Mazmanian, H. Detruit, A. Chapelier, P. Herve and the Paris-Sud University lung transplantation group, J. Appl. Physiol., 82, 1058 (1997).
9. S. Hemmerich and S.D. Rosen, Biochemistry, 33, 4830 (1994).
10. C. Galustian, A.M. Lawson, S. Komba, H. Ishida, M. Kiso and T. Feizi, Biochem. Biophys. Res. Commun., 240, 748 (1997).
11. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
12. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
13. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
14. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
15. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
16. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
17. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
18. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
19. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
20. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
21. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
22. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
23. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
24. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
25. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
26. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
27. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
28. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
29. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
30. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
31. x derivatives have already been prepared: K.C. Nicolaou, N.J. Bockovich and D.R. Carcanague, J. Am. Chem. Soc., 115, 8843 (1993); P.R. Scudder, K. Shailubhai, K.L. Duffin, P.R. Streeter and G.S. Jacob, Glycobiology, 4, 929 (1994); R.K. Jain, R. Vig, R. Rampai, E.V. Chandrasekaran and K.L. Matta, J. Am. Chem. Soc., 116, 12123 (1994); S. Numomura, M. Iida, M. Numata, M. Sugimoto and T. Ogawa, Carbohydr. Res., 263, cl (1994); E.V. Chandrasekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 34, 2925 (1995); R. Vig, R.K. Jain and K.L. Matta, Carbohydr. Res., 266, 279 (1995); A. Hasegawa, K. Ito, H. Ishida and M. Kiso, J. Carbohydr. Chem., 14, 353 (1995); H. Maeda, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 369 (1995); H. Maeda, K. Ito, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 14, 387 (1995); W.J. Sanders, T.R. Katsumoto, C.R. Bertozzi, S.D. Rosen and L. Kiessling, Biochemistry, 35, 14862 (1996); G. V. Reddy, R.K. Jain, R.D. Locke and K.L. Matta. Carbohydr. Res., 280, 261 (1996); M. Yoshida, Y. Kawakami, H. Ishida, M. Kiso and A. Hasegawa, J. Carbohydr. Chem., 15, 399 (1996); S. Komba, H. Ishida, M. Kiso and A. Hasegawa, Carbohydr. Res., 285, Cl (1996); T. Tsukida, M. Yoshida, K. Kurokawa, Y. Nakai, t. Achiha, T. Kiyoi and H. Kondo, J. Org. Chem., 62, 6876 (1997); K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita and Y. Hiramatsu, J. Med. Chem., 40, 455 (1997); A. Koenig, R. Jain, R. Vig, K.E. Norgard-Sumnicht, K.L. Matta and A. Varki, Glycobiology, 7, 79 (1997); B. Huang, R.D. Locke, R.K. Jain and K.L. Matta, Bioorg. Med. Chem. Lett., 7, 1157 (1997); R. Roy, W.K.C. Park, D. Zanini, C. Foxall and O.M.P. Srivastava, Carbohydr. Lett., 3, 259 (1997); Y. Zhang, A. Brodzky and P. Sinay, Tetrahedron: Asymmetry, 9, 2451 (1998); W.J. Sanders, E.J. Gordon, O. Dwir, P.J. Beck, R. Alon and L.L. Kiessling, J. Biol. Chem., 274, 5271 (1999). S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi and M. Kiso, Angew. Chem. Int. Ed., 38, 1131 (1999).
32. E.V. Chandra, Sekaran, R.K. Jain, R.D. Larsen, K. Wlasichuk, R.A. DiCioccio and K.L. Matta, Biochemistry, 35, 8925 (1996).
33. S. Sato, Y. Ito, T. Nukada, Y. Nakahara and T. Ogawa, Carbohydr. Res., 167, 197 (1987).
34. G. Balavoine, S. Berteina, A. Gref, J.-C. Fischer and A. Lubineau, J. Carbohydr. Chem., 14, 1237 (1995).
35. A. Lubineau, J. Le Gallic and R. Lemoine, Bioorg. Med. Chem., 2, 1143 (1994).
36. H. Lönn, Carbohydr. Res., 139, 105 (1985).
37. P.H. Amvam-Zollo and P. Sinaÿ, Carbohydr. Res., 150, 199 (1986).
38. T. Fukuyama, A.A. Laird and L.M. Hotchkiss, Tetrahedron Lett., 26, 6291 (1985); J. Peyton III, P.S. Callery, A.T. Shulgin and N. Castagnoli Jr., J. Org. Chem., 41, 3627 (1976).
39. T. Fukuyama, A.A. Laird and L.M. Hotchkiss, Tetrahedron Lett., 26, 6291 (1985); J. Peyton III, P.S. Callery, A.T. Shulgin and N. Castagnoli Jr., J. Org. Chem., 41, 3627 (1976).
40. H. Paulsen and M. Paal, Carbohydr. Res., 137, 39 (1985).
41. B. Classon, P.J. Garegg and B. Samuelsson, Acta Chem. Scand. B, 38, 4192 (1984).
42. A. Lubineau and R. Lemoine, Tetrahedron Lett., 35, 8795 (1994); B. Guilbert, N.J. Davis, Melanie Pearce, R.T. Aplin and S.L. Flitsch, Tetrahedron: Asymmetry, 5, 2163 (1994).
43. A. Lubineau and R. Lemoine, Tetrahedron Lett., 35, 8795 (1994); B. Guilbert, N.J. Davis, Melanie Pearce, R.T. Aplin and S.L. Flitsch, Tetrahedron: Asymmetry, 5, 2163 (1994).
44. C. Galustian, A. Lubineau, C. Le Narvor, M. Kiso, G. Brown and T. Feizi, J. Biol. Chem., 274, 18213 (1999).