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Efficient and Selective Synthesis of Biologically Active Compounds Related to Nucleic Acid by Uranyl Complex Catalyst

Research Project

Project/Area Number 63470076
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionGunma University

Principal Investigator

SAWAI Hiroaki  Gunma University, Faculty of Engineering, Professor, 工学部, 教授 (70012648)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥5,700,000 (Direct Cost: ¥5,700,000)
Fiscal Year 1989: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1988: ¥4,700,000 (Direct Cost: ¥4,700,000)
KeywordsNucleic Acid / Biologically Active Compounds / Uranyl Complex / Oligonucleotide / 2'-5' Internucleotide Bond / Pyrophosphate Bond / Selective Synthesis / Metal Ion Catalyst / 核酸関連生理活性物質 / 核酸-金属錯体 / 2´- 5´結合
Research Abstract

1. Various nucleoside-5-phosphorimidazolides were prepared from nucleotides such as adenylic acid uridylic acid, cytidylic acid, guanilic acid and 8-azide-adenylic acid, with imidazole and azole compounds such as benzimidazole and triazoles. 2. Using urany complex catalyst which was formed from uranyl nitrate and nucleoside-5'- phosphporimidazolide, the nucleoside-5'-phosphporimidazolide were polymerized.
3. Analysis of the products by high performance liquid chromatography revealed that oligonucleotides from dimer to hexadecamer were formed in high yields. 4. The selectivity of 2'5'-internucleotide bond was 65 - 98%. The type, yield and the regioselectivity of the resulting oligonucleotides were greatly dependent on the pH of the medium, reaction temperature and the concentration of the catalyst. The polymerization took place most efficiently under neutral conditions. 5. Nucleoside-5'- phosphporimidazolides with any nucleic acid bases were polymerized by uranyl complex catalysts forming the corresponding oligonucleotides, though the type of the resulting oligonucleotides were different depending on the type of nucleic acid base used.
6. Hg2+ or Ag+ ion coordinated to the base part exclusively and altered the selectivity of the oligocytidylate formation by uranyl complex catalyst. Use of azole compounds as a nucleotide activating group in the place of imidazole changed the rate, selectivity and yield of the uranyl-ion complex catalyzed oligonucleotide synthesis. 7. Further we have found that Mn2+ and Cd2+ facilitate the pyrophosphate bond formation of nucleotides through the different type of metal-nucleotide complex. 8. Applying the above reaction, we prepared some biologically active nucleotides such as 2-5A analogues, coenzymes and dinucleoside polyphosphates.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] H.Sawai: "Oligonucleotide Formatjion Catalyzed bu Divalent Metal Ions.The Uniqueness of the Ribosyl System" J.Mol.Evol.27. 181-186 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sawai: "Efficient Oligoadenylate Synthesis Catalyzed by Uranyl Ion Complex in Aqueous Solution" Nucleic Acid Res.Sp.Ser.19. 5-7 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sawai,T.Hojo and K.Kuroda: "Uranyl Ion as a highly Efficient Catalyst for the Internucleotide Bond Formation" Bull.Chem.Soc.Jpn. 62. 2018-2023 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sawai,T.Shibusawa and K.Kuroda: "Uranyl Ion Catalyzed Oligonucleotide Synthesis from Adenosine-5'-Phosphorimidazolide.The Effect of Azoles as Nucleotide Activating Groups" Nucleic Acid Res.Sp.Ser.21. 91-92 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sawai: "Divalent Metal Ion-Mediated Phosphodiester Bond Formation from Adenosine-5'-phosphorimidazolide with Glycolic Acid or Lactic Acid.A Nonenzymatic Model Reaction for Nucleotidyl Transfer" Bull.Chem.Soc.Jpn(in press). 63. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Shimizu,K.Shinozuka and H.Sawai: "Facile Synthesis of Nucleotide Containing Polyphosphate by Mn(II)and Cd(II)Ion Catalyzed Pyrophosphate Bond Formation" Tetrahedron Lett.(in press). 31. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sawai: "Oligonucleotide Formation Catalyzed by Divalent Metal Ions. The Uniqueness of the Ribosyl System" J. Mol. evol. 27, 181-186 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sawai: "Efficient Oligoadenylate Synthesis Catalyzed by Uranyl Ion Complex in Aqueous Solution" Nucleic Acid Res. Sp. Ser., 19, 5-7 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sawai, T. Hojo and K. Kuroda: "Uranyl Ion as a Highly Efficient Catalyst for the Internucleotide Bond Formation" Bull. Chem. Soc. Jpn, 62, 2018-2023 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sawai, T. Shibusawa and K. Kuroda: "Uranyl Ion Catalyzed Oligonucleotide Synthesis from Adenosine-5'-phosphorimidazolide. The Effect of Azoles as Nucleotide Activating Groups" Nucleic Acid Res. Sp. Ser., No. 21, 91-92 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sawai: "Divalent Metal Ion-Mediated Phosphodiester Bond Formation from Adenosine-5'-phosphorimidazolide with Glycolic Acid or Lactic Acid. A Nonenzymatic Model Reaction for Nucleotidyl Transfer" Bull. Chem. Soc. Jpn, 63 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Shimazu, K. Shinozuka and H. Sawai: "Facile Synthesis of Nucleotide Containing Polyphosphate by Mn(II) and Cd(II) Ion Catalyzed Pyrophosphate Bond Formation" Tetrahedron Lett., 31 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sawai,T.Hojo and K.Kuroda: "Uranyl Ion as a Highly Efficient Catalyst for the Internucleotide Bond Formation" Bull.Chem.Soc.Jpn. 62. 2018-2023 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] H.Sawai,T.Shibusawa and K.Kuroda: "Uranyl Ion Catalyzed Oligonucleotide Synthesis from Adenosine-5'-phosphorimidazolide.The Effect of Azoles as Nucleotide Activating Groups" Nucleic Acid Res.Sp.Ser.21. 91-92 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] H.Sawai: "Divalent Metal Ion-Mediated Phosphodiester Bond Formation from Adenosine-5'-phosphorimidazolide with Glycolic Acod or Lactic Acid.A Nonenzymatic Model Reaction for Nucleotidyl Transfer" Bull.Chem.Soc.Jpn.63. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Shimazu,K.Shinozuka and H.Sawai: "Facile Synthesis of Nucleotide Containing Polyphosphate by Mn(II)and Cd(II)-Ion Catalyzed Pyrophosphate Bond Formation" Tetrahedron Lett.31. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] H.Sawai: Nucleic Acid Res.Sp.Ser.19. 5-7 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Sawai: J.Mol.Evol.27. 181-186 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Sawai: Bull.Chem.Soc.Japan. 62. (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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