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Synthesis of Saccharide Chain by Using Cells and the Conversion to Functional Polymer

Research Project

Project/Area Number14350483
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionThe University of Tokyo

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)

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)
Project Period (FY) 2002 – 2004
Project Status Completed(Fiscal Year 2004)
Budget Amount *help
¥12,700,000 (Direct Cost : ¥12,700,000)
Fiscal Year 2004 : ¥3,500,000 (Direct Cost : ¥3,500,000)
Fiscal Year 2003 : ¥4,000,000 (Direct Cost : ¥4,000,000)
Fiscal Year 2002 : ¥5,200,000 (Direct Cost : ¥5,200,000)
KeywordsSaccharide Primer / Saccharide Polymer / Saccharide Synthesis / Glycolipid / Glycosyl Transferase / Glycoside / Fluorous / Ganglioside / 二重結合 / アジド化合物 / 細胞内糖鎖伸長 / 糖鎖高分子
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 … More 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

Report

(4results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report

Research Products

(26results)

All 2005 2004 2003 Other

All Journal Article Book Publications

  • [Journal Article] Efficient Sialylation on Azidododecyl Lactosides by Using B16 Meranoma Cells2005

    • Author(s)
      Y.Murozuka, M.C.Kasuya, M.Kobayashi, Y.Watanabe, T.Sato, K.Hatanaka
    • Journal Title

      Chemistry & Biodiversity 2(in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Cellular Uptake and Saccharide Chain Elongation of "Fluoro-Amphiphilic" Glycosides2005

    • Author(s)
      M.C.Kasuya, A.Ito, R.Cusi, T.Sato, K.Hatanaka
    • Journal Title

      Chemistry Letters 34(in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effect of Anomeric Linkage on the Sialylation of Glycosides by Cells2005

    • Author(s)
      M.C.Kasuya, M.Ikeda, K.Hashimoto, T.Sato, K.Hatanaka
    • Journal Title

      Journal of Carbohydrate Chemistry 24(in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Efficient Sialylation on Azidododecyl Lactosides by Using B16 Meranoma Cells2005

    • Author(s)
      Y.Murozuka, M.C.Kasuya, M.Kobayashi, Y.Watanabe, T.Sato, K.Hatanaka
    • Journal Title

      Chemistry & Biodiversity 2 (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Cellular Uptake and Saccharide Chain Elongation of "Fluoro-Amphiphilic" Glycosides2005

    • Author(s)
      M.C.Kasuya, A.Ito, R.Cusi, T.Sato, K.Hatanaka
    • Journal Title

      Chemistry Letters 34 (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effect of Anomeric Linkage on the Sialylation of Glycosides by Cells2005

    • Author(s)
      M.C.Kasuya, M.Ikeda, K.Hashimoto, T.Sato, K.Hatanaka
    • Journal Title

      Journal of Carbohydrate Chemistry 24 (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Efficient Sialylation on Azidododecyl Lactosides by Using B16 Meranoma Cells2005

    • Author(s)
      Y.Murozuka, M.C.Kasuya, M.Kobayashi Y.Watanabe, T.Sato, K.Hatanaka
    • Journal Title

      Chemistry & Biodiversity 2(in press)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Fluorous-tagged compound : a viable scaffold to prime oligosaccharide synthesis by cellular enzymes2004

    • Author(s)
      M.C.Kasuya, R.Cusi, O.Ishihara, A.Miyagawa, K.Hashimoto, T.Sato, K.Hatanaka
    • Journal Title

      Biochemical and Biophysical Research Communications 316・3

      Pages : 599-604

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Display of Azido Glycoside on a Sensor Chip2004

    • Author(s)
      T.Sato, S.Fujita, M.C.Kasuya, K.Hatanaka, T.Yamagata
    • Journal Title

      Chemistry Letters 33・5

      Pages : 580-581

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] 末端に官能基を有する糖鎖プライマーへの細胞による糖鎖伸長2004

    • Author(s)
      畑中研一, 小林雅樹, 粕谷マリアカルメリタ
    • Journal Title

      生産研究 56・3

      Pages : 234-238

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Fluorous-tagged compound : a viable scaffold to prime oligosaccharide synthesis by cellular enzymes2004

    • Author(s)
      M.C.Kasuya, R.Cusi, O.Ishihara, A.Miyagawa, K.Hashimoto, T.Sato, K.Hatanaka
    • Journal Title

      Biochemical and Biophysical Research Communications 316-2

      Pages : 599-604

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Display of Azido Glycoside on a Sensor Chip2004

    • Author(s)
      T.Sato, S.Fujita, M.C.Kasuya, K.Hatanaka, T.Yamagata
    • Journal Title

      Chemistry Letters 33-5

      Pages : 580-581

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Convenient Synthetic Method for 1,2,3,6-Tetra-O-Acetyl-β-D-Glucopyranose : A Starting Material for β(1→4)-D-Glucan2004

    • Author(s)
      K.Hatanaka, S.Takakura, K.Okuyama, M.C.Kasuya, K.-I.Kanno
    • Journal Title

      Polymer journal 36・7

      Pages : 567-569

    • Related Report
      2004 Annual Research Report
  • [Journal Article] ジ-O-カルボキシメチル-β-シクロデキストリンの合成と反応2004

    • Author(s)
      畑中研一, 片岡直人, 粕谷マリアカルメリタ, 奥山光作, 田村潔, 橋本和彦
    • Journal Title

      高分子論文集 61・12

      Pages : 613-616

    • Related Report
      2004 Annual Research Report
  • [Book] ソフトマテリアルの新展開2004

    • Author(s)
      西敏夫ほか41名
    • Total Pages
      302
    • Publisher
      シーエムシー出版
    • Related Report
      2004 Annual Research Report
  • [Book] バイオマテリアルサイエンス2003

    • Author(s)
      石原一彦, 畑中研一, 山岡哲二, 大矢裕一
    • Total Pages
      206
    • Publisher
      東京化学同人
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] M.C.Z.Kasuya, K.Hatanaka, et al.: "Fluorous-tagged compound : a viable scaffold to prime oligosaccharide synthesis by cellular enzymes"Biochem.Biophys.Res.Commun.. 316. 599-604 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Katsuraya, K.Okuyama, K.Hatanaka, et al.: "Constitution of konjac glucomannnan : chemical analysis and 13C NMR spectroscopy"Carbohydr.Polym.. 53. 183-189 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] A, Kai, M.Kikawa, K.Hatanaka, et al.: "Biosynthesis of hetero-polysaccharides by Pestalotiopsis microspora from various monosaccharides as carbon sorce"Carbohydr.Polym.. 54. 381-383 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 石原一彦, 畑中研一, 山岡哲二, 大矢裕一: "バイオマテリアルサイエンス"東京化学同人. 206 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 畑中研一, 白石竜司, 鬘谷要, 奥山光作: "主鎖中にオリゴ糖鎖を有する芳香族ポリエステルの合成"日本化学会誌. 2002・1. 53-55 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 畑中研一, 栗原史恵, 久能めぐみ, 奥田章博, 柏谷マリアカルメリタ: "バイオインスパイアード糖質高分子による線維芽細胞増殖因子(FGF)の活性化"日本化学会誌. 2002・2. 155-158 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] J.S.Klutts, K.Hatanaka, Y.T.Pan, A.D.Elbein: "Biosynthesis of D-Arabinose in Mycobacterium smegmatis : Specific Labeling from D-Glucose"Archives of Biochemistry and Biophysics. 398・2. 229-239 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.C.Kasuya, H.Sugita, K.Okuyama, K.Katsuraya, K.: "Facile Synthesis of β(1→6)-Linked Gluco-Oligosaccharide Derivatives"Polymer Journal. 34・8. 618-620 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 畑中研一, 粕谷マリアカルメリタ: "糖質高分子"日本接着学会誌. 38・9. 334-339 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 畑中 研一: "生体は糖鎖高分子をどのように認識しているか"化学. 57・6. 27-31 (2002)

    • Related Report
      2002 Annual Research Report

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Published : 2002-04-01   Modified : 2016-04-21  

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