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

• Published in: Carbohydrate research Vol. 339; no. 17; pp. 2749 - 2759
• Main Authors: Yamamura, Takeshi, Hada, Noriyasu, Kaburaki, Asuka, Yamano, Kimiaki, Takeda, Tadahiro
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 06.12.2004; Elsevier
• Subjects: 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; Echinococcus multilocularis; Glycosphingolipids; Chemical synthesis; Benzoyl ceramide; chemical synthesis; GLYCOSIDES; CELL-SURFACE GLYCANS; METACESTODES; ANALOGS; glycosphingolipids; CERAMIDE; HIGHLY STEREOSELECTIVE-SYNTHESIS
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2004.09.015

[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).