S-linked ganglioside analogues for use in conjugate vaccines

被引：70

作者：

Rich, JR ^{[1
]}

Bundle, DR ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Alberta Ingenu Ctr Carbohydrate Sci, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 06期

关键词：

D O I：

10.1021/ol036460p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.

引用

页码：897 / 900

页数：4

共 40 条

[1] Conformational differences between Fuc(α1-3)GlcNAc and its thioglycoside analogue
Aguilera, B
Jiménez-Barbero, J
Fernández-Mayoralas, A
[J]. CARBOHYDRATE RESEARCH, 1998, 308 (1-2) : 19 - 27
[2] CARBOHYDRATE TRIFLATES - REACTION WITH NITRITE, LEADING DIRECTLY TO EPI-HYDROXY COMPOUNDS
ALBERT, R
DAX, K
LINK, RW
STUTZ, AE
[J]. CARBOHYDRATE RESEARCH, 1983, 118 (JUL) : C5 - C6
[3] A SIMPLE METHOD FOR THE PREPARATION OF THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID
BENNETT, S
VONITZSTEIN, M
KIEFEL, MJ
[J]. CARBOHYDRATE RESEARCH, 1994, 259 (02) : 293 - 299
[4] Bitton RJ, 2002, ONCOL REP, V9, P267
[5] Synthesis and immunostimulating activity of a thioglycolipopeptide glycomimetic as a potential anticancer vaccine derived from Tn antigen
Bousquet, E
Spadaro, A
Pappalardo, MS
Bernardini, R
Romeo, R
Panza, L
Ronsisvalle, G
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 2000, 19 (4-5) : 527 - 541
[6] Danishefsky SJ, 2000, ANGEW CHEM INT EDIT, V39, P836, DOI 10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO
[7] 2-I
[8] Defaye J., 1991, STUDIES NATURAL PROD, V8, P315
[9] Driguez H, 1997, TOP CURR CHEM, V187, P85
[10] Driguez H, 2001, CHEMBIOCHEM, V2, P311

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