TY - JOUR
T1 - Synthetic studies on glycosphingolipids from protostomia phyla
T2 - Synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni
AU - Kanaya, Takayuki
AU - Schweizer, Frank
AU - Takeda, Tadahiro
AU - Kiuchi, Fumiyuki
AU - Hada, Noriyasu
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (No. 22590014) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and the Strategic Research Foundation at Private Universities of the MEXT. We gratefully acknowledge financial support in the form of the Uehara Memorial Foundation. The authors are grateful to Ms. J. Hada for providing HR-FABMS measurement data.
PY - 2012/11/1
Y1 - 2012/11/1
N2 - Stereocontrolled syntheses of three neutral glycosphingolipids and six oligosaccharide derivatives found from the parasite Schistosoma mansoni have been accomplished. A pentasaccharide glycosphingolipid β-d-Galp-(1→4)- [α-l-Fucp-(1→3)]-β-d-GlcpNAc-(1→3)-β-d-GalpNAc- (1→4)-β-d-Glcp-(1↔1)-Cer (1), two hexasaccharide glycosphingolipids α-l-Fucp-(1→3)-β-d-Galp-(1→4)-[α- l-Fucp-(1→3)]-β-d-GlcpNAc-(1→3)-β-d-GalpNAc-(1→4) -β-d-Glcp-(1↔1)-Cer (2) and β-d-Galp-(1→4)-[α-l-Fucp- (1→3)]-β-d-GlcpNAc-(1→3)-β-d-GlcpNAc-(1→3) -β-d-GalpNAc-(1→4)-β-d-Glcp-(1↔1)-Cer (3), together with their non-reducing end tri- and tetrasaccharides, β-d-Galp-(1→4)- [α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (4) and α-l-Fucp-(1→3) -β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (5), were synthesized by block synthesis. Moreover, non-reducing end oligosaccharides of schistosomal glycosphingolipids, β-d-GalpNAc-(1→4)-[α-l- Fucp-(1→3)]-β-d-GlcpNAcOR (6), α-l-Fucp-(1→3)-β-d- GalpNAc-(1→4)-[α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (7), α-l-Fucp-(1→3)-β-d-GalpNAc-(1→4)-[α-l-Fucp-(1→2) -α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (8) and α-l-Fucp-(1→3) -β-d-GalpNAc-(1→4)-[α-l-Fucp-(1→2)-α-l-Fucp- (1→2)-α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (9) [R = 2-(trimethylsilyl)ethyl], were synthesized as probes to explore their diagnostic potential to detect schistosomiasis from patients' sera.
AB - Stereocontrolled syntheses of three neutral glycosphingolipids and six oligosaccharide derivatives found from the parasite Schistosoma mansoni have been accomplished. A pentasaccharide glycosphingolipid β-d-Galp-(1→4)- [α-l-Fucp-(1→3)]-β-d-GlcpNAc-(1→3)-β-d-GalpNAc- (1→4)-β-d-Glcp-(1↔1)-Cer (1), two hexasaccharide glycosphingolipids α-l-Fucp-(1→3)-β-d-Galp-(1→4)-[α- l-Fucp-(1→3)]-β-d-GlcpNAc-(1→3)-β-d-GalpNAc-(1→4) -β-d-Glcp-(1↔1)-Cer (2) and β-d-Galp-(1→4)-[α-l-Fucp- (1→3)]-β-d-GlcpNAc-(1→3)-β-d-GlcpNAc-(1→3) -β-d-GalpNAc-(1→4)-β-d-Glcp-(1↔1)-Cer (3), together with their non-reducing end tri- and tetrasaccharides, β-d-Galp-(1→4)- [α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (4) and α-l-Fucp-(1→3) -β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (5), were synthesized by block synthesis. Moreover, non-reducing end oligosaccharides of schistosomal glycosphingolipids, β-d-GalpNAc-(1→4)-[α-l- Fucp-(1→3)]-β-d-GlcpNAcOR (6), α-l-Fucp-(1→3)-β-d- GalpNAc-(1→4)-[α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (7), α-l-Fucp-(1→3)-β-d-GalpNAc-(1→4)-[α-l-Fucp-(1→2) -α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (8) and α-l-Fucp-(1→3) -β-d-GalpNAc-(1→4)-[α-l-Fucp-(1→2)-α-l-Fucp- (1→2)-α-l-Fucp-(1→3)]-β-d-GlcpNAcOR (9) [R = 2-(trimethylsilyl)ethyl], were synthesized as probes to explore their diagnostic potential to detect schistosomiasis from patients' sera.
KW - Glycosphingolipid
KW - Schisto-core
KW - Schistosoma mansoni
KW - Stereocontrolled synthesis
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U2 - 10.1016/j.carres.2012.08.008
DO - 10.1016/j.carres.2012.08.008
M3 - Article
C2 - 22982172
AN - SCOPUS:84866017818
SN - 0008-6215
VL - 361
SP - 55
EP - 72
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -
