Synthesis of the starfish ganglioside LLG-3 tetrasaccharide |
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| Authors: | Shinya Hanashima Daichi Ishikawa Ken-ichi Sato |
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| Affiliation: | a Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama, Kanagawa 221-8686, Japan
b Structural Glycobiology Team, Systems Glycobiology Research Group, Chemical Biology Department, Advanced Science Institutes, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan |
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| Abstract: | The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection. |
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| Keywords: | Ganglioside Sialic acid N-Glycolylneuraminic acid Glycosylation |
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