2000 Fiscal Year Final Research Report Summary
Synthetic studies on the unnatural glycan-linked dolichylpyrophosphates
| Project/Area Number |
11660116
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Tokai University |
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Principal Investigator |
NAKAHARA Yoshiaki Dept. of Industrial Chemistry, Professor, 工学部, 教授 (50087574)
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| Co-Investigator(Kenkyū-buntansha) |
HOJO Hironobu Dept. of Industrial Chemistry, Associate Professor, 工学部, 助教授 (00209214)
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| Project Period (FY) |
1999 – 2000
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| Keywords | dolichylpyrophosphate / asparagine-linked oligosaccharide / biosynthesis of N-glycan / lipid-intermediate |
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| Research Abstract |
In the biosynthesis of asparagine-linked glycoprotein oligosaccharides, glycan chains grow on a common lipid-intermediate by glycosyltransferases. The chain growing processes have not been well studied because of inaccessibility of the unstable glycosyl dolichylpyrophosphates. There have been a few reports describing the chemical synthesis of N-acetylglucosaminyl, and chitobiosyl dolichylpyrophosphates.
On the other hand, we have been interested in the structural requirement of N-glycans in the carbohydrate-mediated biological interactions, In this project, we planned the synthesis of dolichylpyrophosphates carrying oligosaccharides with unnatural glycosidic linkage, which would be the useful probes for the studies of glycan biosynthesis. Before going to the dolichyl pyrophosphate chemistry, the synthetic routes to the N-glycan core pentasaccharides of unnatural structure were investigated. The unnatural α mannoside was derived from the side product of insoluble Ag-mediated mannosylation while α GlcNAc linkage was established using the 2-azidoglucose derivative as a glycosyl donor.
The synthesis of the glycosylated dolichylpyrophosphate was next investigated according to the reported synthetic procedures. In order to facilitate monitoring of the reactions especially in the coupling reaction of glycosyl phosphate and dolichyl phosphate, p-toluoyl group was used for the protection of sugar hydroxyl group. The toluoylated intermediates were readily detectable on TLC plates. The GlcNAc-linked dolichylpyrophosphate was synthesized in 20% yield by this method.
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