Synthesis of Aminoethyl Glycosides of the Carbohydrate Chains of Glycolipids Gb3, Gb4, and Gb5

Russian Journal of Bioorganic Chemistry

Volumn 29, Issue 4, 2003, Pages 372-381

  Cheshev, P E ^a   Khatuntseva, E A ^a   Gerbst, A G ^a   Tsvetkov, Yu E ^a   Shashkov, A S ^a   Nifantiev, N E ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Aminoethyl glycosides, glycosylation; Globosides; Glycolipids Gb3, Gb4, and Gb5

Indexed keywords

2 AZIDOETHYL (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) (1-4) (2,3,6 TRI O BENZOYL DEXTRO GALACTOPYRANOSYL) (1-4) 2,3,6 TRI O BENZOYL BETA DEXTRO GLUCOPYRANOSIDE; 2 AZIDOETHYL (3 O ACETYL 2,4,6 TRI O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) (1-4) (2,3,6 TRI O BENZOYL BETA DEXTRO GALACTOPYRANOSYL) (1-4) 2,3,6 TRI O BENZOYL BETA DEXTRO GLUCOPYRANOSIDE; 2 AZIDOETHYL 2,3,6 TRI O BENZOYL 4 O (2,3,6 TRI O BENZOYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO GLUCOPYRANOSIDE; 4 TRICHLOROACETAMIDOPHENYL 3,4,6 TRI O ACETYL 2 DEOXY 1 THIO 2 TRICHLOROACETAMIDO BETA DEXTRO GALACTOPYRANOSIDE; 4 TRICHLOROACETAMIDOPHENYL 4,6 DI O ACETYL 2 DEOXY 3 O (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 1 THIO 2 TRICHLOROACETAMIDO BETA DEXTRO GALACTOPYRANOSIDE; ACETIC ACID DERIVATIVE; AZIDE; CARBOHYDRATE; DICHLOROMETHANE; FLUOROFORM; GLUCOPYRANOSIDE; GLYCOLIPID; GLYCOSIDE; N IODOSUCCINIMIDE; PENTASACCHARIDE; SUCCINIMIDE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIFLUOROMETHANESULFONIC ACID METHYL ESTER; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEACETYLATION; GLYCOSYLATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0042711023     PISSN: 10681620     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1024905419008     Document Type: Article

References (20)

1. Kannagi, R., Levery, S.B., Ishingami, F., Hakomori, S.-I., Slevinsky, L.H., Knowles, B.B., and Solter, D., J. Biol. Chem., 1983, vol. 258, pp. 8934-8942.
2. Ohyama, C., Orikasa, S., Kawamura, S., Satoh, M., Saito, S., Fukushi, Y., Hakomori, S., and Levery, S.B., Cancer, 1995, vol. 76, pp. 1043-1050.
3. Naiki, M. and Marcus, D.M., Biochemistry, 1975, vol. 14, pp. 4837-4841.
4. Normark, S., Baga, M., Goransson, M., Lindberg, F.P., Lund, B., Norgren, M., and Uhlin, B.-E., Microbial Lectins and Agglutinins, Mirelman, D., Ed., New York: Whiley, 1986, pp. 113-143.
5. Nicolau, K.C., Caulfield, T., Kataoka, H., and Kumazawa, T., J. Am. Chem. Soc., 1988, vol. 110, pp. 7910-7912.
6. Qui, D. and Schmidt, R.R., Liebigs Ann. Chem., 1992, pp. 217-224.
7. Koike, K., Sugimoto, M., Sato, S., Ito, Y., Nakahara, Y., and Ogawa, T., Carbohydr. Res., 1987, vol. 163, pp. 189-208.
8. Nunomura, S. and Ogawa, T., Tetrahedron Lett., 1988, vol. 29, pp. 5681-5684.
9. Paulsen, H. and Bunsch, A., Carbohydr. Res., 1982, vol. 101, pp. 21-30.
10. Leontein, K., Nilsson, M., and Norberg, T., Carbohydr. Res., 1985, vol. 144, pp. 231-240.
11. Ishida, H., Miyawaki, R., Kiso, M., and Hasegawa, A., J. Carbohydr. Chem., 1996, vol. 15, pp. 163-182.
12. Lassaletta, J.M., Carlsson, K., Garegg, P.J., and Schmidt, R.R., J. Org. Chem., 1996, vol. 61, pp. 6873-6880.
13. Zou, W., Brisson, J.-R., Laroque, S., Gardner, R.L., and Jennings, H.J., Carbohydr. Res., 1999, vol. 315, pp. 251-261.
14. Baer, H.H. and Saeed, A.A., Carbohydr. Res., 1980, vol. 84, pp. 53-60.
15. Baer, H.H. and Saeed, A.A., Carbohydr. Res., 1979, vol. 77, pp. 117-129.
16. Byramova, N.E., Ovchinnikov, M.V., Backinowsky, L.V., and Kochetkov, N.K., Carbohydr. Res., 1983, vol. 123, pp. 8-11.
17. Lonn, H., Carbohydr. Res., 1985, vol. 139, pp. 105-113.
18. Sherman, A.A., Mironov, Y.V., Yudina, O.N., and Nifantiev, N.E., Carbohydr. Res., 2003, vol. 338, pp. 697-703.
19. Cheshev, P.E., Kononov, L.O., Tsvetkov, Yu.E., Shashkov, A.S., and Nifantiev, N.E., Bioorg. Khim., 2002, vol. 28, pp. 462-473.
20. Nifantiev, N.E., Bakinovskii, L.V., Lipkind, G.M., Shashkov, A.S., and Kochetkov, N.K., Bioorg. Khim., 1991, vol. 17, pp. 517-530.