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1993 Fiscal Year Final Research Report Summary

CHEMICAL SYNTHESIS OF A NEW MATERIAL OF ANTISENSE NUCLEIC ACID"2"PHOSTHORYLATEDRNAS" DIRETED TOWARD IIS BASIC STRUCTRAL STUDIES AND REGULATION OF EXPRESSION OF HIV VIRUS-

Research Project

Project/Area Number 04453031
Research Category

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

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionTOKYO INSTITUTE OF TECHNOLOGY

Principal Investigator

SEKINE Mitsuo  TOKYO INSTITUTE OF TECHNOLOGY, FACULTY OF BIOSCIENCE AND BIOTECHNOLOGY, ASSOCIATE PROFESSOR, 生命理工学部, 助教授 (40111679)

Co-Investigator(Kenkyū-buntansha) WADA Takeshi  TOKYO INSTITUTE OF TECHNOLOGY, FACULTY OF BIOSCIENCE AND BIOTECHNOLOGY, RESEARCH, 生命理工学部, 助手 (90240548)
Project Period (FY) 1992 – 1993
KeywordsANTISENCE NUCLEIC ACID / 2'-PHOSPHATE / RNA / CHEMICALSYNTHESIS / HIV / SOLID PHASE SYNTHESIS / ENZYME RESISTANCE / AMIDITE
Research Abstract

This year, we have tried to study the development of new organic reactions required for the synthesis of 2'-phosphorylated RNAs. As the result, we have achieved the following results : First, we found that bis(2-cyano-1, 1-diamethylethyl)phosphoryl can be used not only as a 2'-hydroxyl protecting groups but also as a precursor of the 2'-phosphate group. This protected phosphoryl group was found to be quite stable upon removal of a 3', 5-cyclic silyl protecting group with HF/Py in dichloromethane and not to migrate from the 3'-2' hydroxyl functions. This finding led us to realize the construction of key intermediates, 2'-phosphorylated 3'-phosphoramide units which were required throughout this study. The builiding units were utilized for the solid phase synthesis of 2'-phosohorylated yridylate derivatives. We could synthesize 2, 4, 6, and 10mers of 2'-phosphorylated uridylated uridylates in good yields. They were found to be resistant to acid and alkaline conditions as well as enzymatic digestion with spleen phosphodiesterase. In particular, the 10 mer proved to have an unique structure as evidenced by NMR.At the present time, we are studying the binding ability of these new nucleic acid derivatives for target DNA or RNA fragments.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] M.Sekine et al.: "Synthesis of a New Class of 2'-Phosphorylated Oligoribonucleotides Capable of Conversion to Oliqoribonucleotides" Journal of Organic Chemistry. 58. 3204-3208 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sekine et al.: "First Method for the Direct P-S Bond Formation from Phosphodiesters and Thiols" Natural Products Letters. 1. 293-298 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sekine et al.: "Selective and Rapid O-Acylation of Hydroxyl Groups of Nucleosides by Phase Transfer Catalysis" Natural Products Letters. 1. 251-256 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sekine et al.: "Sumultaneous Removal of Two 2-Cyano-1,1-dimethylethyl Groups from Bis(2-Cyano-1,1-dimethylethyl)thymidine 3^1-Phosphate Der." Natural Products Letters. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sekine et al.: "Synthesis and Properties of N-Tritylthio Nucleoside Dervatives" Journal Chemical Society,Perkin Trans.1. 3087-3093 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sekine et al.: "Synthesis of a New Class of 2'-Phosphorylated Oligoribonucleotides Capable of Conversion to Oligoribonucleotides" Joumal of Organic Chemistry. 58. 3204-3208 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sekine et al.: ""First Method for the Direct P-S Bond Formation from Phosphodiesters and Thiols"" Natural Products Letters. 1. 293-298 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sekine et al.: ""Selective and Rapid O-Acylation of Hydroxyl Groups of Nucleosides by Phase Transfer Catalysis"" Natural Products Letters. 1. 251-256 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sekine et al.: ""Sumultaneous Removal of Two 2-Cyano-1, 1-dimethylethyl Groups from Bis(2-cyano-1, 1-dimethylethjyl) thimidine 3'-Phosphate Derivatives"" Natural Products Letters. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sekine et al.: ""Synthesis and Properties of N-Tritylthio Nucleoside Derivatives"" Joumal of Chemical Society, Perkin Trans.1. 3087-3093 (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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