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
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (No. 19590011) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT), and High-Tech Research Center project of the MEXT. The authors are grateful to Ms. J. Hada for providing HR-FAB MS data.
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
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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 -