Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

Carbohydrate Research

Volumn 338, Issue 10, 2003, Pages 1045-1054

  Asnani, Ari ^a   Auzanneau, France Isabelle ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Lewis X analogues; Oligosaccharide synthesis; Reversed phase HPLC; Thiophenyl glycosides

Indexed keywords

ANTIBODIES; ANTIGENS; PROTEINS; SYNTHESIS (CHEMICAL);

IMMUNOGENS;

GLUCOSE;

2,4,6 TRI O ACETYL 4 O (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ALLYL 2,6 DI O BENZOYL 4 O (2,6 DI O BENZOYL 3,4 O ISOPROPYLIDENE BETA DEXTRO GALACTOPYRANOSYL) 3 O [3,4 O ISOPROPYLIDENE 2 O (4 METHOXYBENZYL) ALPHA LEVO FUCOPYRANOSYL] BETA DEXTRO GLUCOPYRANOSIDE; ALLYL 3 O (4 O ACETYL 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL) 2,6 DI O BENZOYL 4 O (2,6 DI O BENZOYL 3,4 O ISOPROPYLIDENE BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO GLUCOPYRANOSIDE; ALLYL 3 O ALPHA LEVO FUCOPYRANOSYL 4 O BETA DEXTRO GALACTOPYRANOSYL BETA DEXTRO GLUCOPYRANOSIDE; ALLYL 4 O BETA DEXTRO GALACTOPYRANOSYL 3 O ALPHA LEVO RHAMNOPYRANOSYL BETA DEXTRO GLUCOPYRANOSIDE; ANTIBODY; ANTIGEN; BROMIDE; CARRIER PROTEIN; FUCOSE; GLUCOSE; N ACETYLGLUCOSAMINE; PHENYL 2,3,4 TRI O ACETYL 1 THIO BETA LEVO FUCOPYRANOSIDE; PHENYL 2,3,4 TRI O ACETYL 1 THIO BETA LEVO RHAMNOPYRANOSIDE; PHENYL 2,6 DI O BENZOYL 4 O (2,6 DI O BENZOYL 3,4 O ISOPROPYLIDENE BETA DEXTRO GALACTOPYRANOSYL) 3 O [3,4 O ISOPROPYLIDENE 2 O (4 METHOXYBENZYL) ALPHA LEVO FUCOPYRANOSYL] 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 3 O (4 O ACETYL 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL) 2,6 DI O BENZOYL (2,6 DI O BENZOYL 3,4 O ISOPROPYLIDENE BETA DEXTRO GALACTOPYRANOSYL) 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 3,4 O ISOPROPYLIDENE 2 O (4 METHOXYBENZYL) 1 THIO BETA LEVO FUCOPYRANOSIDE; PHENYL 4 O ACETYL 2,3 O ISOPROPYLIDINE 1 THIO BETA LEVO RHAMNOPYRANOSIDE; RHAMNOSE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ANTIGEN BINDING; ARTICLE; CHEMICAL ANALYSIS; DEPROTECTION REACTION; DONOR; DRUG CONJUGATION; DRUG PURIFICATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0037403608     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00053-3     Document Type: Article

References (36)

1. Hakomori S.-I. Adv. Cancer Res. 52:1989;257-331.
2. Hakomori S.-I., Zhang Y. Chem. Biol. 4:1997;97-104.
3. Hakomori S.-I. Acta Anat. 161:1998;79-90.
4. Danishefsky S.J., Allen J.R. Angew. Chem., Int. Ed. Engl. 39:2000;837-863.
5. Wang Z.G., Williams L.J., Zhang X.-F., Zatorski A., Kudryashov V., Ragupathi G., Spassova M., Bornmann W., Slovin S.F., Scher H.I., Livingston P.O., Lloyd K.O., Danishefsky S.J. Proc. Natl. Acad. Sci. USA. 97:2000;2719-2724.
6. 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.I. Proc. Natl. Acad. Sci. USA. 96:1999;5710-5715.
7. Toyokuni T., Singhal A.K. Chem. Soc. Rev. 1995;231-242.
8. King C.A., Stevenson F.K. Chem. Ind. 7:1997;266-269.
9. Livingston, P.O.; Ritter, G.J.; Oettegen, H.F.; Old, L.J. US Patent 5,102,663, 1992.
10. Fukushi Y., Hakomori S.-I., Nudelman E., Cochran N. J. Biol. Chem. 259:1984;4681-4685.
11. Fukushi Y., Hakomori S.-I., Shepard T. J. Exp. Med. 159:1984;506-520.
12. Fukushi Y., Kannagi R., Hakomori S.-I., Shepard T., Kulander B.G., Singer J.W. Cancer Res. 45:1985;3711-3717.
13. Itzkowitz S.H., Yuan M., Fukushi Y., Palekar A., Phelps P.C., Shamsuddin A.M., Trump B.T., Hakomori S.-I., Kim Y.S. Cancer Res. 46:1986;2627-2632.
14. Nakasaki H., Mitomi T., Noto T., Ogoshi K., Hanaue H., Tanaka Y., Makuuchi H., Clausen H., Hakomori S.-I. Cancer Res. 49:1989;3662-3669.
15. Zhang S., Zhang H.S., Cordon-Cardo C., Reuter V.E., Singhal A.K., Lloyd K.O., Livingston P.O. Int. J. Cancer. 73:1997;50-56.
16. Auzanneau F.-I., Pinto B.M. Bioorg. Med. Chem. 4:1996;2003-2010.
17. Zhu T., Boons G.-J. J. Am. Chem. Soc. 122:2000;10222-10223. and references cited therein.
18. Windmüller R., Schmidt R.R. Tetrahedron Lett. 35:1994;7927-7930. and references cited therein.
19. Terada T., Simada H., Ishida H., Kiso M., Hasegawa A. J. Carbohydr. Chem. 17:1998;519-534.
20. Tsukida T., Yoshida M., Kurokawa K., Nakai Y., Achiba T., Kiyoi T., Kondo H. J. Org. Chem. 62:1997;6876-6881.
21. Yoshida M., Kiyoi T., Tsukida T., Kondo H. J. Carbohydr. Chem. 17:1998;673-681.
22. Fraser Reid B., Wu Z., Udodong U.E., Ottosson H. J. Org. Chem. 55:1990;6068-6070.
23. Fischer E., Delbrück K. Ber. 42:1909;1476-1482.
24. Purves C.B. J. Am. Chem. Soc. 51:1929;3619-3627.
25. Tropper F.D., Andersson F.O., Grand-Maître C., Roy R. Synthesis. 1991;734-736.
26. Hasegawa A., Fushimi K., Ishida H., Kiso M. J. Carbohydr. Chem. 12:1993;1203-1216.
27. Kahne, D.E.; Loebach, J.; Yan, L.; Liang, Int. Patent Application WO 97/35202, 1997.
28. Kim S.-H., Augeri D., Yang D., Kahne D. J. Org. Chem. 116:1994;1766-1775.
29. Pozgay V., Jennings H. J. Org. Chem. 53:1988;4042-4052.
30. Ferrier R.J., Furneaux R.H. Carbohydr. Res. 52:1976;63-68.
31. Bock K., Pedersen C. J. Chem. Soc., Perkin Trans. 2. 1974;293-297.
32. Auzanneau F.-I., Bundle D.R. Can. J. Chem. 71:1993;534-548.
33. Nashed M.A., Musser J.H. Carbohydr. Res. 250:1993;C1-C4.
34. Bartek J., Müller R., Kosma P. Carbohydr. Res. 308:1998;259-273.
35. Gordon A.J., Ford R.A. A Chemist's Companion. 1972;429-436 John Wiley & Sons Inc, New York.
36. Kartha K.P.R., Jennings H.R. J. Carbohydr. Chem. 9:1990;777-781.