Synthesis of N-acetylglucosamine containing Lewis A and Lewis X building blocks based on N-tetrachlorophthaloyl protection - Synthesis of Lewis X pentasaccharide

Carbohydrate Research

Volumn 310, Issue 3, 1998, Pages 157-171

  Lay, Luigi ^a   Manzoni, Leonardo ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Disaccharide, Trisaccharide building blocks; Glycosylation; Lewis A; Lewis X; N tetrachlorophthaloyl; Protection; Trichloroacetimidates

Indexed keywords

DISACCHARIDE; N ACETYLGLUCOSAMINE; PENTASACCHARIDE; TRISACCHARIDE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; BREAST MILK; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; NONHUMAN; PRIORITY JOURNAL; PROTECTION;

ACETYLGLUCOSAMINE; ANTIGENS, CD15; CARBOHYDRATE SEQUENCE; DISACCHARIDES; LEWIS BLOOD-GROUP SYSTEM; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PHTHALIC ACIDS; TRISACCHARIDES;

EID: 0031689853     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00148-7     Document Type: Article

References (44)

1. S. Hakomori, Adv. Cancer Res., 52 (1989) 257-331; J. Biol. Chem., 265 (1990) 18713-18716; T. Feizi and R.A. Childs, Trends Biochem. Sci., (1985) 24- 29;
2. S. Hakomori, Adv. Cancer Res., 52 (1989) 257-331; J. Biol. Chem., 265 (1990) 18713-18716; T. Feizi and R.A. Childs, Trends Biochem. Sci., (1985) 24- 29;
3. S. Hakomori, Adv. Cancer Res., 52 (1989) 257-331; J. Biol. Chem., 265 (1990) 18713-18716; T. Feizi and R.A. Childs, Trends Biochem. Sci., (1985) 24-29;
4. J. Koscielak, Glycoconjugate J., 3 (1986) 95-108 .
5. R.R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 50 (1994) 21-123; H.G. Garg, K. von dem Bruch, and R.R. Schmidt, Adv. Carbohydr. Chem. Biochem., 50 (1994) 277-310, and references therein.
6. R.R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 50 (1994) 21-123; H.G. Garg, K. von dem Bruch, and R.R. Schmidt, Adv. Carbohydr. Chem. Biochem., 50 (1994) 277-310, and references therein.
7. R.U. Lemieux, T. Takeda, and B.Y. Chung, ACS Symp. Ser., 39 (1976) 90-115; J. Banoub, P. Boullanger, and D. Lafont, Chem. Rev., 92 (1992) 1167-1195; D. Lafont and P. Boullanger, J. Carbohydr. Chem., 11 (1992) 567-586, and references therein.
8. R.U. Lemieux, T. Takeda, and B.Y. Chung, ACS Symp. Ser., 39 (1976) 90-115; J. Banoub, P. Boullanger, and D. Lafont, Chem. Rev., 92 (1992) 1167-1195; D. Lafont and P. Boullanger, J. Carbohydr. Chem., 11 (1992) 567-586, and references therein.
9. R.U. Lemieux, T. Takeda, and B.Y. Chung, ACS Symp. Ser., 39 (1976) 90-115; J. Banoub, P. Boullanger, and D. Lafont, Chem. Rev., 92 (1992) 1167-1195; D. Lafont and P. Boullanger, J. Carbohydr. Chem., 11 (1992) 567-586, and references therein.
10. J.C. Castro-Palomino and R.R. Schmidt, Tetrahedron Lett., 36 (1995) 5343-5346.
11. W. Dullenkopf, J.C. Castro-Palomino, L. Manzoni, and R.R. Schmidt, Carbohydr. Res., 296 (1996) 135-147.
12. H. Paulsen and B. Helpap, Carbohydr. Res., 216 (1991) 289-313.
13. E. Meinjohanns, M. Meldal, H. Paulsen, and K. Bock, J. Chem. Soc., Perkin Trans 1 (1995) 405-415; K.J. Jensen, P.R. Hansen, D. Venugopal, and G. Barany, J. Am. Chem. Soc., 118 (1996) 3148- 3155.
14. E. Meinjohanns, M. Meldal, H. Paulsen, and K. Bock, J. Chem. Soc., Perkin Trans 1 (1995) 405- 415; K.J. Jensen, P.R. Hansen, D. Venugopal, and G. Barany, J. Am. Chem. Soc., 118 (1996) 3148-3155.
15. R.R. Schmidt, Angew. Chem., 98 (1986) 213-236; Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235; H. Paulsen, Angew. Chem., 94 (1982) 184; Angew. Chem. Int. Ed. Engl., 21 (1982) 155; Chem. Soc. Rev., (1984) 15.
16. R.R. Schmidt, Angew. Chem., 98 (1986) 213-236; Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235; H. Paulsen, Angew. Chem., 94 (1982) 184; Angew. Chem. Int. Ed. Engl., 21 (1982) 155; Chem. Soc. Rev., (1984) 15.
17. R.R. Schmidt, Angew. Chem., 98 (1986) 213-236; Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235; H. Paulsen, Angew. Chem., 94 (1982) 184; Angew. Chem. Int. Ed. Engl., 21 (1982) 155; Chem. Soc. Rev., (1984) 15.
18. R.R. Schmidt, Angew. Chem., 98 (1986) 213-236; Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235; H. Paulsen, Angew. Chem., 94 (1982) 184; Angew. Chem. Int. Ed. Engl., 21 (1982) 155; Chem. Soc. Rev., (1984) 15.
19. R.R. Schmidt, Angew. Chem., 98 (1986) 213-236; Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235; H. Paulsen, Angew. Chem., 94 (1982) 184; Angew. Chem. Int. Ed. Engl., 21 (1982) 155; Chem. Soc. Rev., (1984) 15.
20. A. Toepfer, W. Kinzy, and R.R. Schmidt, Liebigs Ann. Chem., (1994) 449-464; A. Toepfer and R.R. Schmidt, Tetrahedron Lett., 33 (1992) 5161-5164, and references therein.
21. A. Toepfer, W. Kinzy, and R.R. Schmidt, Liebigs Ann. Chem., (1994) 449-464; A. Toepfer and R.R. Schmidt, Tetrahedron Lett., 33 (1992) 5161-5164, and references therein.
22. N.M. Spijker, P. Westerduin, and C.A.A. van Boeckel, Tetrahedron, 48 (1992) 6297; Y. Matsuzaki, Y. Ito, Y. Nakahara, and T. Ogawa, Tetrahedron Lett., 34 (1993) 1061-1064; F.A.W. Kolman, J.W.G. Meisener, H.R.P. van Ritter, J.P. Kamerling, and J.F.G. Vliegenthart, J. Carbohydr. Chem., 13 (1994) 1.
23. N.M. Spijker, P. Westerduin, and C.A.A. van Boeckel, Tetrahedron, 48 (1992) 6297; Y. Matsuzaki, Y. Ito, Y. Nakahara, and T. Ogawa, Tetrahedron Lett., 34 (1993) 1061-1064; F.A.W. Kolman, J.W.G. Meisener, H.R.P. van Ritter, J.P. Kamerling, and J.F.G. Vliegenthart, J. Carbohydr. Chem., 13 (1994) 1.
24. N.M. Spijker, P. Westerduin, and C.A.A. van Boeckel, Tetrahedron, 48 (1992) 6297; Y. Matsuzaki, Y. Ito, Y. Nakahara, and T. Ogawa, Tetrahedron Lett., 34 (1993) 1061-1064; F.A.W. Kolman, J.W.G. Meisener, H.R.P. van Ritter, J.P. Kamerling, and J.F.G. Vliegenthart, J. Carbohydr. Chem., 13 (1994) 1.
25. J.S. Debenham, R. Madsen, C. Roberts, and B. Fraser-Reid, J. Am. Chem. Soc., 117 (1995) 3302-3303.
26. J.C. Castro-Palomino and R.R. Schmidt, Tetrahedron Lett., 36 (1995) 5343-5346; Liebigs Ann., (1996) 1623-1626.
27. J.C. Castro-Palomino and R.R. Schmidt, Tetrahedron Lett., 36 (1995) 5343-5346; Liebigs Ann., (1996) 1623-1626.
28. J. Debenham, Rodebaugh, and B. Fraser-Reid, Liebigs Ann., (1997) 791-802.
29. U.K. Saha, L.S. Griffith, J. Rademann, A. Geyer, and R.R. Schmidt, Carbohydr. Res., 304 (1997) 21-28.
30. x epitopes, see ref [9].; A. Toepfer and R.R. Schmidt, J. Carbohydr. Chem., 12 (1993) 809-822; R. Windmüller and R.R. Schmidt, Tetrahedron Lett., 35 (1994) 7927- 7930; J. Natunen, R. Niemela, L. Penttila, A. Seppo, T. Ruohtula, and O. Renkonen, Glycobiology, 4 (1994) 577; G. Hummel and R.R. Schmidt, Tetrahedron Lett., 38 (1997) 1173-1176, and references therein.
31. x epitopes, see ref [9].; A. Toepfer and R.R. Schmidt, J. Carbohydr. Chem., 12 (1993) 809-822; R. Windmüller and R.R. Schmidt, Tetrahedron Lett., 35 (1994) 7927-7930; J. Natunen, R. Niemela, L. Penttila, A. Seppo, T. Ruohtula, and O. Renkonen, Glycobiology, 4 (1994) 577; G. Hummel and R.R. Schmidt, Tetrahedron Lett., 38 (1997) 1173-1176, and references therein.
32. x epitopes, see ref [9].; A. Toepfer and R.R. Schmidt, J. Carbohydr. Chem., 12 (1993) 809-822; R. Windmüller and R.R. Schmidt, Tetrahedron Lett., 35 (1994) 7927- 7930; J. Natunen, R. Niemela, L. Penttila, A. Seppo, T. Ruohtula, and O. Renkonen, Glycobiology, 4 (1994) 577; G. Hummel and R.R. Schmidt, Tetrahedron Lett., 38 (1997) 1173-1176, and references therein.
33. x epitopes, see ref [9].; A. Toepfer and R.R. Schmidt, J. Carbohydr. Chem., 12 (1993) 809-822; R. Windmüller and R.R. Schmidt, Tetrahedron Lett., 35 (1994) 7927- 7930; J. Natunen, R. Niemela, L. Penttila, A. Seppo, T. Ruohtula, and O. Renkonen, Glycobiology, 4 (1994) 577; G. Hummel and R.R. Schmidt, Tetrahedron Lett., 38 (1997) 1173-1176, and references therein.
34. L. Manzoni, L. Lay, and R.R. Schmidt, J. Carbohydr. Chem., in press.
35. G. Zemplén, Ber. Dtsch. Chem. Ges., 60 (1927) 1555-1564.
36. R.R. Schmidt and M. Stumpp, Liebigs Ann. Chem., (1983) 1249-1256; P.H. Amvam-Zollo and P. Sinaÿ, Carbohydr. Res., 150 (1986) 199; S. Sato, Y. Ito, T. Nukuda, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 167 (1987) 197.
37. R.R. Schmidt and M. Stumpp, Liebigs Ann. Chem., (1983) 1249-1256; P.H. Amvam-Zollo and P. Sinaÿ, Carbohydr. Res., 150 (1986) 199; S. Sato, Y. Ito, T. Nukuda, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 167 (1987) 197.
38. R.R. Schmidt and M. Stumpp, Liebigs Ann. Chem., (1983) 1249-1256; P.H. Amvam-Zollo and P. Sinaÿ, Carbohydr. Res., 150 (1986) 199; S. Sato, Y. Ito, T. Nukuda, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 167 (1987) 197.
39. R. Windmüller, Dissertation, University of Konstanz, 1995; T. Eisele, R. Windmüller, and R.R. Schmidt, Carbohydr. Res., in press.
40. R. Windmüller, Dissertation, University of Konstanz, 1995; T. Eisele, R. Windmüller, and R.R. Schmidt, Carbohydr. Res., in press.
41. U. Greilich, R. Brescello, K-H. Jung, and R.R. Schmidt, Liebigs Ann., (1996) 663-672.
42. N.M. Spijker, C.A. Keuning, M. Hooglugt, G.H. Veeneman, and C.A.A. van Boeckel, Tetrahedron, 52 (1996) 5945-5960.
43. L. Lay, R. Windmüller, S. Reinhardt, and R.R. Schmidt, Carbohydr. Res., 303 (1997) 39-49.
44. O. Kanie, S.C. Crawley, M.A. Palcic, and O. Hindsgaul, Carbohydr. Res., 243 (1993) 139-164.