Selective protection of 2-azido-lactose and in situ ferrier rearrangement during glycosylation: Synthesis of a dimeric lewis x fragment

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3585-3588

  Wang, An ^a   Auzanneau, France Isabelle ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FERRIER REARRANGEMENT GLYCOSYLATION; GLYCOSYL ACCEPTORS; IN SITU FERRIER REARRANGEMENT;

ANTIGENS; CARBOHYDRATES; DIMERS; IN SITU PROCESSING; SYNTHESIS (CHEMICAL);

GLYCOSYLATION;

2 AZIDOLACTOSE; CANCER VACCINE; CARBOHYDRATE ANTIGEN; LACTOSE; TRISACCHARIDE; TUMOR ANTIGEN; UNCLASSIFIED DRUG;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; DRUG DESIGN; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; VACCINE PRODUCTION;

ANTIGENS, CD15; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CHEMISTRY, ORGANIC; DIMERIZATION; GALACTOSE; GLYCOSYLATION; LACTOSE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA;

EID: 34247607100     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062541y     Document Type: Article

References (34)

1. Hakomori, S.-I.; Jeanloz, R. W. J. Biol. Chem. 1964, 239, 3606-3607.
2. Hakomori, S.-I.; Koscielak, J.; Bloch, K. J.; Jenaloz, R. W. J. Immunol. 1967, 98, 31-38.
3. Hakomori, S.-I. Adv. Cancer Res. 1989, 52, 257-331.
4. Hakomori, S.-I.; Zhang, Y. Chem. Biol. 1997, 4, 97-104.
5. Hakomori, S.-I. Acta Anat. 1998, 161, 79-90.
6. Toyokuni, T.; Singhal, A. K. Chem. Soc. Rev. 1995, 231-242.
7. King, C. A.; Stevenson, F. K. Chem. Ind. 1997, 7, 266-269.
8. Livingston, P. O.; Ritter, G. J.; Oettegen, H. F.; Old, L. J. U.S. Patent 5,102,663, 1992.
9. Slovin, S. F.; Ragupathi, G.; Alduri, S.; Ungers, G.; Terry, K.; Kim. S.; Spassova, M.; Bornmann, W. G.; Fazzari, M.; Dantis, L.; Olkiewicz, K.; Lloyd, K. O.; Livingston, P. O.; Danishefsky, S. J.; Scher, H. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 5710-5715.
10. Dube, D. H.; Bertozzi, C. Nat. Rev. Drug Discovery 2005, 4, 477-488.
11. Fukushi, Y.; Hakomori, S.-I.; Nudelman, E.; Cochran, N. J. Biol. Chem. 1984, 259, 4681-4685.
12. Fukushi, Y.; Hakomori, S.-I.; Shepard, T. J. Exp. Med. 1984, 159, 506-520.
13. Fukushi, Y.; Kannagi, R.; Hakomori, S.-I.; Shepard, T.; Kulander, B. G.; Singer, J. W. Cancer Res. 1985, 45, 3711-3717.
14. Lemieux, R. U.; Ratcliffe, R. M. U.S. Patent 4,195,174, 1980.
15. Beth-Halami, D.; Flowers, H. M.; Shapiro, D. Carbohydr. Res. 1967, 5, 25-30.
16. Hasegawa, A.; Fushimi, K.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1993, 12, 1203-1216.
17. Mukhopadhyay, B.; Field, R. A. Carbohydr. Res. 2003, 338, 2149-2152.
18. Jung, K. H.; Hoch, M.; Schmidt, R. R. Liebigs Ann. Chem. 1989, 1099-1106.
19. La Ferla, B.; Prosperi, D.; Lay, L.; Russo, G.; Panza, L. Carbohydr. Res. 2002, 337, 1333-1342.
20. (a) Jiang, L.; Chan, T.-H. J. Org. Chem. 1998, 63, 6035-6038.
21. (b) Sato, K.-I.; Seki, H.; Yoshitomo, A.; Nanaumi, H.; Takai, Y.; Ishido, Y. J. Carbohydr. Chem. 1998, 17, 703-727.
22. Nashed, E. M.; Glaudemans, C. P. J. J. Org. Chem. 1987, 52, 5255-5260.
23. (a) Hannelore, H. V.; Brandstetter, H.; Zbiral, E. Helv. Chim. Acta 1978, 61, 1832-1841.
24. (b) Sim, M. M.; Kondo, H.; Wong, C-H. J. Am. Chem. Soc. 1993, 115, 2260-2267.
25. (c) Lin, C.-C; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826-6840.
26. Lemieux, R. U.; Takeda, T.; Chung, B. Y. ACS Symp. Ser. 1976, 39, 90-113.
27. Grundler, G.; Schmidt, R. R. Carbohydr. Res. 1985, 135, 203-218.
28. Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570-575.
29. Ferrier, R. J.; Sankey, G. H. J. Chem. Soc. C 1966, 2345-2349.
30. Silva, M. M.; Cleophax, J.; Benicio, A. A.; Almeida, M. V.; Delaumeny, J.-M.; Machado, A. S.; Gero, S. D. Synlett 1996, 8, 764-766.
31. Maranduba, A.; Veyrieres, A. Carbohydr. Res. 1986, 151, 105-119.
32. Lonn, H. Carbohydr. Res. 1985, 139, 105-113.
33. La Ferla, B.; Lay, L.; Russo, G.; Panza, L. Tetrahedron: Asymmetry 2000, 11, 3647-3651.
34. La Ferla, B.; Prosperi, D.; Lay, L.; Russo, G.; Panza, L. Carbohydr. Res. 2002, 337, 1333-1342.