2004 Fiscal Year Final Research Report Summary
Synthesis of Saccharide Chain by Using Cells and the Conversion to Functional Polymer
| Project/Area Number |
14350483
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
高分子合成
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| Research Institution | The University of Tokyo |
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Principal Investigator |
HATANAKA Kenichi The University of Tokyo, Center for Collaborative Research, Professor, 国際・産学共同研究センター, 教授 (70167584)
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| Co-Investigator(Kenkyū-buntansha) |
KASUYA Maria Carmelita The University of Tokyo, Institute of Industrial Science, Research Associate, 生産技術研究所, 助手 (30334361)
SATO Toshinori Keio University, Faculty of Biosciences and Informatics, Professor, 理工学部, 教授 (00162454)
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| Project Period (FY) |
2002 – 2004
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| Keywords | Saccharide Primer / Saccharide Polymer / Saccharide Synthesis / Glycolipid / Glycosyl Transferase / Glycoside / Fluorous / Ganglioside |
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| Research Abstract |
In order to establish the optimum condition for the bio-production of a large amount of valuable materials containing GM3-type oligosaccharides, two kinds of lactoside primers having azido group at different positions were synthesized and introduced into B16 melanoma cells. The synthesis of primers I and II was accomplished by glycosylation of 12-azido-1-dodecanol and 2-azido-1-dodecanol, respectively, with lactose peracetate and subsequent deacetylation.
Both primers were glycosylated to give GM3-type oligosaccharide derivatives which were released to the culture medium. The amount of glycosylated product from primer II (2-azidododecyl β-lactoside) was almost twice as compared with that from primer I (12-azidododecyl β-lactoside). The effects of seeded cell number, primer concentration and length of incubation time on the glycosylation efficiency were also investigated. The results are necessary to optimize the conditions for the mass-production of GM3-type oligosaccharide using azido
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dodecyl lactoside primer and B16 cells. Fluorous-tagged saccharide primers could be viable scaffolds for the synthesis of oligosaccharides. This research demonstrates that a fluorine-containing saccharide derivative could actually be taken up by the cell, the saccharide chain elongated by cellular enzymes, and the elongated product released by the cells to the culture medium.
A fluorous-tagged lactoside primer, 6-(perfluorohexyl)hexyl-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside, was chemically synthesized and introduced in mouse B16 cells to prime oligosaccharide synthesis. Uptake of the primer by B16 cells resulted in the sialylation of the terminal galactose residue to afford an oligosaccharide with the same glycan structure as ganglioside GM3. The presence of many fluorine atoms did not have any adverse effects to the cells. Moreover, the number of fluorine atoms did not pose a steric barrier and instead, their presence possibly increased the hydrophobicity of the primer and enhanced membrane permeability. This strategy of using a fluorous-tagged primer and cells can pave the way for an easier way of preparing oligosaccharides via an environment-friendly approach that eliminates the use of large amounts of organic solvents. Less
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