Journal
CARBOHYDRATE RESEARCH
Volume 344, Issue 7, Pages 856-868Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2009.02.019
Keywords
Glycoprotein; Echinococcus multilocularis; Host-parasite interactions; Stereocontrolled syntheses
Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT) [19590011]
- High-Tech Research Center project of the MEXT
- Grants-in-Aid for Scientific Research [19590011] Funding Source: KAKEN
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Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Gal beta 1 -> 3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1 -> 3(GlcNAc beta 1 -> 6)GalNAc alpha 1-OR (A). tetrasaccharide Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 6)GalNac alpha 1-OR(D), and pentasaccharides Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 4Gl cNAc beta 1-6)GalNAc alpha 1-OR (E) and Gal beta 1-3(Gal alpha 1 -> 4Gal alpha 1 -> 4Gal alpha 1 -> 6)GalNAc alpha 1-OR) (F) (R = 2(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-P-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharicles. Moreover, linear trisaccharide Gal beta 1 -> Gal beta 1 -> 3GalNac alpha 1-OR (B) and branched tetrasaccharide Gal beta 1 -> Gal beta 1 -> 3(GalNac beta 1 -> 6)GalNac alpha 1-OR (C) were synthesized by stepwise condensation. (C) 2009 Elsevier Ltd. All rights reserved.
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