Abstract
Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Galβ1→3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (A), tetrasaccharide Galβ1→3(Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (D), and pentasaccharides Galβ1→3(Galβ1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (E) and Gal β1→3(Galα1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (F) (R = 2-(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharides. Moreover, linear trisaccharide Galβ1→4Galβ1→3GalNAcα1-OR (B) and branched tetrasaccharide Galβ1→4Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (C) were synthesized by stepwise condensation.
| Original language | English |
|---|---|
| Pages (from-to) | 856-868 |
| Number of pages | 13 |
| Journal | Carbohydrate Research |
| Volume | 344 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 2009 May 12 |
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Keywords
- Echinococcus multilocularis
- Glycoprotein
- Host-parasite interactions
- Stereocontrolled syntheses
ASJC Scopus subject areas
- Biochemistry
- Analytical Chemistry
- Organic Chemistry
Cite this
Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcus multilocularis. / Koizumi, Akihiko; Hada, Noriyasu; Kaburaki, Asuka; Yamano, Kimiaki; Schweizer, Frank; Takeda, Tadahiro.
In: Carbohydrate Research, Vol. 344, No. 7, 12.05.2009, p. 856-868.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcus multilocularis
AU - Koizumi, Akihiko
AU - Hada, Noriyasu
AU - Kaburaki, Asuka
AU - Yamano, Kimiaki
AU - Schweizer, Frank
AU - Takeda, Tadahiro
PY - 2009/5/12
Y1 - 2009/5/12
N2 - Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Galβ1→3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (A), tetrasaccharide Galβ1→3(Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (D), and pentasaccharides Galβ1→3(Galβ1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (E) and Gal β1→3(Galα1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (F) (R = 2-(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharides. Moreover, linear trisaccharide Galβ1→4Galβ1→3GalNAcα1-OR (B) and branched tetrasaccharide Galβ1→4Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (C) were synthesized by stepwise condensation.
AB - Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Galβ1→3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (A), tetrasaccharide Galβ1→3(Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (D), and pentasaccharides Galβ1→3(Galβ1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (E) and Gal β1→3(Galα1→4Galβ1→4GlcNAcβ1→6)GalNAcα1-OR (F) (R = 2-(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharides. Moreover, linear trisaccharide Galβ1→4Galβ1→3GalNAcα1-OR (B) and branched tetrasaccharide Galβ1→4Galβ1→3(GlcNAcβ1→6)GalNAcα1-OR (C) were synthesized by stepwise condensation.
KW - Echinococcus multilocularis
KW - Glycoprotein
KW - Host-parasite interactions
KW - Stereocontrolled syntheses
UR - http://www.scopus.com/inward/record.url?scp=64949142510&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=64949142510&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2009.02.019
DO - 10.1016/j.carres.2009.02.019
M3 - Article
C2 - 19286169
AN - SCOPUS:64949142510
VL - 344
SP - 856
EP - 868
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 7
ER -