| Project/Area Number |
63560122
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
製造化学・食品
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| Research Institution | GIFU UNIVERSITY |
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Principal Investigator |
HASEGAWA Akira Gifu University, Department of Applied Bioorganic Chemistry, Professor, 農学部, 教授 (10026429)
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| Co-Investigator(Kenkyū-buntansha) |
KISO Makoto Gifu University, Department of Applied Bioorganic Chemistry, Associate Professor, 農学部, 助教授 (90092931)
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| Project Period (FY) |
1988 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,600,000 (Direct Cost: ¥1,600,000)
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| Keywords | Synthesis of Gangliosides / Sialoglycoconjugate / Sialic acid / alpha-selective glycosidation of Sialic acids / Synthesis of Thioanalogs of Gangliosides / シアログリココンジュゲイト / 細胞表層複合糖脂質 / 機能性生体糖脂質 / 免疫 / 発ガン / 分化誘導関連生体成分 |
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| Research Abstract |
Sialic acids are well known as constituents of glycoprotein and glycolipids of cell membranes, and they play a role in biological recognition and many other biological functions. It is also known that naturally occurring sialo compounds contain sialic acids in alpha-glycosidic linkage, except for CMP-N-acetylneuraminic acid. Therefore, a facile regio- and alpha-selective glycoside synthesis of N-acetylneuraminic acid is critically important, in order to investigate the structure-function relationships of such sialoglycoconjugates as glycoproteins and gangliosides. Glycosidation of methyl (5-acetamido-4,7,8,9-tetra-0-acetyl-3,5-dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosyl chloride)onate as the glycosyl donor with sugar derivatives usually gives a mixture of alpha- and beta- glycoside. When reacting with secondary hydroxyl groups of sugar derivatives, this donor affords the expected a-glycosides in very low yields. We demonstrated that the methyl alpha-thioglycoside of Neu5Ac derivative are useful glycosyl donor to afford alpha-glycosides of Neu5Ac by use of dimethyl(methylthio)sulfonium triflate (DMTST) and the suitably protected glycosyl acceptors, in acetonitrile under kinetically controlled conditions. We have achieved to synthesize a variety of gangliosides and the analogs by using this methodology.
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