Synthetic studies on glycosphingolipids from Protostomia phyla: total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis
[Display omitted] 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 prese...
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| Published in | Carbohydrate research Vol. 339; no. 17; pp. 2749 - 2759 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Elsevier Ltd
06.12.2004
Elsevier |
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| Abstract | [Display omitted]
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). |
|---|---|
| AbstractList | 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).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). 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). 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). (C) 2004 Elsevier Ltd. All rights reserved. [Display omitted] 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). |
| Author | Yamamura, Takeshi Takeda, Tadahiro Hada, Noriyasu Kaburaki, Asuka Yamano, Kimiaki |
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| Keywords | Echinococcus multilocularis Glycosphingolipids Chemical synthesis Benzoyl ceramide chemical synthesis GLYCOSIDES CELL-SURFACE GLYCANS METACESTODES ANALOGS glycosphingolipids CERAMIDE HIGHLY STEREOSELECTIVE-SYNTHESIS |
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Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of
Echinococcus... Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been... |
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| SubjectTerms | Animals Benzoyl ceramide Biochemistry & Molecular Biology Carbohydrate Conformation Carbohydrate Sequence carbohydrate structure Chemical synthesis Chemistry Chemistry, Applied Chemistry, Organic echinococcosis Echinococcus multilocularis Echinococcus multilocularis - chemistry Glycosphingolipids Glycosphingolipids - chemical synthesis Glycosphingolipids - chemistry Glycosylation Life Sciences & Biomedicine Molecular Sequence Data Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Physical Sciences Science & Technology synthesis |
| Title | Synthetic studies on glycosphingolipids from Protostomia phyla: total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis |
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