Synthetic studies on glycosphingolipids from Protostomia phyla: Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis

Takeshi Yamamura; Noriyasu Hada; Asuka Kaburaki; Kimiaki Yamano; Tadahiro Takeda

doi:10.1016/j.carres.2004.09.015

Synthetic studies on glycosphingolipids from Protostomia phyla: Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis

Takeshi Yamamura, Noriyasu Hada, Asuka Kaburaki, Kimiaki Yamano, Tadahiro Takeda

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).

Original language	English
Pages (from-to)	2749-2759
Number of pages	11
Journal	Carbohydrate Research
Volume	339
Issue number	17
DOIs	https://doi.org/10.1016/j.carres.2004.09.015
Publication status	Published - 2004 Dec 6
Externally published	Yes

Keywords

Benzoyl ceramide
Chemical synthesis
Echinococcus multilocularis
Glycosphingolipids

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2004.09.015

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title = "Synthetic studies on glycosphingolipids from Protostomia phyla: Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis",

abstract = "Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).",

keywords = "Benzoyl ceramide, Chemical synthesis, Echinococcus multilocularis, Glycosphingolipids",

author = "Takeshi Yamamura and Noriyasu Hada and Asuka Kaburaki and Kimiaki Yamano and Tadahiro Takeda",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 14771250) from the Ministry of Education, Science, Sports and Culture of Japan. The authors are grateful to Ms. J. Hada for providing NMR and MS data.",

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doi = "10.1016/j.carres.2004.09.015",

language = "English",

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journal = "Carbohydrate Research",

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T2 - Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis

AU - Yamamura, Takeshi

AU - Hada, Noriyasu

AU - Kaburaki, Asuka

AU - Yamano, Kimiaki

AU - Takeda, Tadahiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 14771250) from the Ministry of Education, Science, Sports and Culture of Japan. The authors are grateful to Ms. J. Hada for providing NMR and MS data.

PY - 2004/12/6

Y1 - 2004/12/6

N2 - Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).

AB - Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).

KW - Benzoyl ceramide

KW - Chemical synthesis

KW - Echinococcus multilocularis

KW - Glycosphingolipids

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Synthetic studies on glycosphingolipids from Protostomia phyla: Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis

Abstract

Keywords

ASJC Scopus subject areas

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