Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni

Takayuki Kanaya, Frank Schweizer, Tadahiro Takeda, Fumiyuki Kiuchi, Noriyasu Hada

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)55-72
Number of pages18
JournalCarbohydrate Research
Volume361
DOIs
Publication statusPublished - 2012 Nov 1

Fingerprint

Glycosphingolipids
Schistosoma mansoni
Parasites
Carbohydrates
Oligosaccharides
Neutral Glycosphingolipids
Trisaccharides
Schistosomiasis
Derivatives
Serum

Keywords

  • Glycosphingolipid
  • Schisto-core
  • Schistosoma mansoni
  • Stereocontrolled synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Synthetic studies on glycosphingolipids from protostomia phyla : Synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni. / Kanaya, Takayuki; Schweizer, Frank; Takeda, Tadahiro; Kiuchi, Fumiyuki; Hada, Noriyasu.

In: Carbohydrate Research, Vol. 361, 01.11.2012, p. 55-72.

Research output: Contribution to journalArticle

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abstract = "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.",
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AU - Kanaya, Takayuki

AU - Schweizer, Frank

AU - Takeda, Tadahiro

AU - Kiuchi, Fumiyuki

AU - Hada, Noriyasu

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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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