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1993 Fiscal Year Final Research Report Summary

Synthesis of Alkyl Oligosaccharide by Ring-Opening Polymerization of Anhydro Sugars

Research Project

Project/Area Number 04453112
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionUniversity of Tokyo

Principal Investigator

URYU Toshiyuki  University of Tokyo, Institute of Industrial Science, Professor, 生産技術研究所, 教授 (80011005)

Co-Investigator(Kenkyū-buntansha) KATSURAYA Kaname  University of Tokyo, Institute of Industrial Science, Research Associate, 生産技術研究所, 助手 (20251465)
YOSHIDA Takashi  Hokkaido University, Faculty of Science, Associate Professor, 理学部, 助教授 (40166955)
Project Period (FY) 1992 – 1993
KeywordsAlkyl oligosaccharide / Oligo-ribose / Ring-opening polymerization / Anhydro sugar / Sulfated alkyl oligo-ribose / Anti-HIV-activity / Glycosidation / Poly-deoxy-ribose
Research Abstract

In our laboratory, following the synthesis of highly anti-HIV (human immunodeficiency virus) active sulfated polysaccharides, sulfated alkyl oligosaccharides with potent anti-HIV activity were prepared. The sulfated alkyl oligosaccharide has such a structure that a long alkyl group is attached to the reducing end of the sulfated oligosaccharide. In this study, modifying the synthetic method of high molecular weight stereoregular polysaccharides, medium molecular weight polysaccharides, i.e., polyriboses, were prepared by selective cationic ring-opening polymerization of a 1,4-anhydro-ribose derivative. The acetylated polyribose, i.e., acetylated (1->5)-alpha-ribofuranan, was reacted with octadecyl alcohol by stannic chloride catalyst to afford acetylated alkyl polyribose with medium molecular weight. After deacetylation, OH-free alkyl oligo-riboses were sulfated into sulfated alkyl oligo-riboses with anti-HIV activity. In addition, a new 1,4-anhydro-deoxy-ribose monomer was synthesized and polymerized into a stereoregular poly-deoxy-ribose. This deoxy-ribose derivative has a potential to be used for the synthesis of another alkyl oligosaccharide.

  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] T.Uryu,K.Katsuraya,T.Yoshida,et al.: "Sulfated Alkyl Oligosaccharides with Potent Inhibitory Effects on Human Immunodeficiency Virus Infection" Biochem.Pharm.43. 2385-2392 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Yoshida,Y.Katayama,S.Inoue,and T.Uryu: "Synthesis of Branched Ribofuranans and Their Sulfates with Potent Anti-AIDS Virus Activity by Selective Ring-Opening Copolymerization of 1,4-Anhydro-α-D-ribopyranose Derivatives" Maclomolecules. 25. 4051-4057 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Uryu: "Artificial Polysaccharides and Their Biological Activities" Progress in Polymer Science. 18. 717-761 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Oda,T.Yoshida,and T.Uryu: "Ring-Opening Polymerization of Modified 1,4-Anhydro-deoxy-ribose Derivatives and Synthesis of 3-Deoxy-(1→5)-α-D-ribofuranan" Maclomolecules. 27. 315-319 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Katsuraya,T.Yoshida,T.Uryu,et al.: "Synthesis of Sulfated Alkyl Malto-oligosaccharides and Laminari-oligosaccharides with Potent Inhibitory Effects on AIDS Virus Infection" Carbohydr.Res.(印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Uryu,S.Y.Choi,T.Yoshida,and K.Katsuraya: "Synthesis of Alkyl Oligosaccharide by Ring-Opening Polymerization of Anhydro Sugars" Carbohydr.Res.(投稿準備中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Uryu,Y.Kaneko,T.Yoshida,R.Mihara,T.Shoji,K.Katsuraya,H.Nakashima,and N.Yamamoto: "“Carbohydrate and Carbohydrate Polymers"" ATL Press, 15 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Uryu, N.Ikushima, K.Katsuraya, T.Shoji, N.Takahashi, T.Yoshida, K.Kanno, H.Nakashima and N.Yamamoto: "Sulfated Alkyl Oligosaccharides with Potent Inhibitory Effects on Human Immunodeficiency Virus Infection" Biochem.Pharm. 43. 2385-2392 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Yoshida, Y.Katayama, S.Inoue and T.Uryu: "Synthesis of Branched Ribofuranans and Their Sulfates with Potent Anti-AIDS Virus Activity by Selective Ring-Opening Copolymerization of 1,4-Anhydro-alpha-D-ribopyranose Derivatives" Maclomolecules. 25. 4051-4057 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Uryu: "Artificial Polysaccharides and Their Biological Activities" Progress in Polymer Science. 18. 717-761 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Oda, T.Yoshida and T.Uryu: "Ring-Opening Polymerization of Modified 1,4-Anhydro-deoxyribose Derivatives and Synthesis of 3-Deoxy-(1->5)-alpha-D-ribofuranan" Maclomolecules. 27. 351-319 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Katsuraya, N.Ikushima, N.Takahashi, T.Shoji, H.Nakashima, N.Yamamoto, T.Yoshida and T.Uryu: "Synthesis of Sulfated Alkyl Malto-oligosaccharides and Laminari-oligosaccharides with Potent Inhibitory Effects on AIDS Virus Infection" Carbohydr.Res.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Uryu, S.Y.Choi, T.Yoshida and K.Katsuraya: "Synthesis of Alkyl Oligosaccharide by Ring-Opening Polymerization of Anhydro Sugars" Carbohydr.Res.(in preparation).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Uryu, Y.Kankeo, T.Yoshida, R.Mihara, T.Shoji, K.Katsuraya, H.Nakashima and N.Yamamoto: ""Carbohydrate and Carbohydrate Polymers" Chapter 10" ATL Press. 67-72 (1993)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1995-03-27  

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