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1993 Fiscal Year Final Research Report Summary

Synthetic Study of Biologically Related Compounds Using Cellulose Derivatives as a Polymer-support

Research Project

Project/Area Number 02403011
Research Category

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

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionTokyo College of Pharmacy

Principal Investigator

ISHIDO Yoshiharu  Tokyo College of Pharmacy, Faculty of Pharmacy, Professor, 薬学部, 教授 (60016037)

Co-Investigator(Kenkyū-buntansha) KAMAIKE Kazuo  Tokyo College of Pharmacy, Faculty of Pharmacy, Research Associate, 薬学部, 助手 (50214507)
KAWASHIMA Etsuko  Tokyo College of Pharmacy, Faculty of Pharmacy, Lecturer, 薬学部, 講師 (30057343)
Project Period (FY) 1990 – 1993
KeywordsA cellulose acetate as a polymer-support / A nucleoside with a modified base / 2'-omicron-(D-Ribofuranosyl)-adenosine / D-Ribofuranosylation / Glycosyl carbamate derivatives / Stable isotope labeled nucleosides / [2'-^2H]-2'-Deoxyribonucleosides / Nucleosides with ^<15>N-labeled exocyclic amino group
Research Abstract

1.Synthetic Study of Oligonucleotides : (1)The cellulose acetate derivatives were found to be feasible for the syntheses of DNA-type8-mer and of RNA-type 13-mer. (2)Development of efficient methods for the protection of functional groups involved in pseudouridine (psi), 1-beta-D-ribofuranosylthymine(rT), 5, 6-dihydrouridine(D), and phosphate, led us to successful syntheses of RNA-type 12-mer involving psi and rT, 11-mer involving 5'-terminal phosphate through the polymer-support, and 8-mer involving D through the CPG-support.
2.Synthetic Study of 2'-omicron-(alpha- and beta-D-ribofuranosyl)adenosines : The alpha-isomer, known as the key compound of poly(ADP-ribose), and the beta-isomer, found as the corresponding 5'-phosphate located at 64th position of Yeast initiator tRNA^<Met>, were synthesized with high stereoselectivity by the acid-catalyzed coupling reaction of an adenosine 2'-hydroxyl derivative with D-ribofuranosyl derivatives functionalized at their anomeric position.
3.Synthetic Study of Oligosaccharides : Novel approaches to glycosylation in terms of acid-catalyzed coupling reaction of a glycosyl acceptor with glycosyl donors bearing 1-phenoxylcarbonate and 1-phenylcarbamate were developed. and the latter was found to be particularly feasible for the synthesis of oligosaccharides such as Le^Y antigenic tetrasaccharide.
4.Synthetic Study of Nucleosides Specifically Labeled with Stable Isotopes : Highly diastereoselective syntheses of (2'R)- and (2'S)-[2'-^2H]-2'-deoxyribonucleosides, and efficient method for the syntheses of nucleosides bearing exocyclic amino groups, were labeled with ^<15>N atom, were realized. These products essentially contribute to the NMR spectroscopic study on delicate conformational analysis on interactions of nucleic acid-nucleic acid or nucleic acid-protein etc.

  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] K.Kamaike: "Synthesis of an Oligonucleotide Bearing a Phosphate Function at the 5'-Terminus Using a Novel Protecting Group in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleosides & Nucleotides. 12. 1015-1032 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] E.Kawashima: "Sonochemical and Triethylborane-induced Tin Deuteride Reduction for the Highly Stereoselective Synthesis of(2'R)-[2'-^2H]-2'-Deoxyribonucleosides from 2'-Functionalized Ribonucleosides" Tetrahedron Lett.34. 1317-1320 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] C.Kojima: "Precise Analyses of DNA Structure by NMR" Nucleic Acids Symposium Series. 29. 185-186 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] E.Kawashima: "Highly Stereoserective Syntheses of(2'R)-[2'-^2H]-2'-Deoxyribonucleosides and Synthesis of their Oligonucleotides" Nucleic Acids Synposium Series. 27. 81-82 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kamaike: "Further Improvement in the Procedure for Oligonucleotide Synthesis in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleosides & Nucleotides. 11. 637-668 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Nishino: "Efficient Deanilidation of Phosphroanilidates by the Use of Nitrites and Acetic Anhydride" Heteroatom Chem.2. 187-196 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kamaike: "Further Improvement in Protecting Method for the Oligonucleotide Synthesis in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleic Acids Res.Symposium Series. 24. 37-39 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 釜池和大: "セルロース誘導体を高分子担体として用いるオリゴヌクレオチドの合成研究" 化学と工業. 43. 926-929 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kamaike: "Oligonucleotide Synthesis in Terms of a Novel Type of Polymer-support;a Cellulose Acetate Functionalized with 4-(2-Hydroxyethylsulfonyl)dihydrocinnamoyl Substituent" Tetrahedron. 46. 163-184 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kamaike, Y.Hasegawa, I.Masuda, Y.Ishido, K.Watanabe, I.Hira, and K.Miura: "Oligonucleotide Synthesis in Terms of a Novel Type of Polymer-support ; a Cellulose Acetate Functionalized with 4-(2-Hydroxyethylsulfonyl)dihydrocinnamoyl Substituent" Tetrahedron. 46. 163-184 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kamaike and Y.Ishido: "Oligonucleotide Synthesis in Terms of a Cellulose Acetate Derivative as a Polymer-support" Kagaku To Kogyo (Chemistry and Chemical Industry). 43. 926-929 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kamaike, T.Ogawa, Y.Inoue, and Y.Ishido: "Further Improvement in Protecting Method for the Oligonucleotide Synthesis in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleic Acids Res.Symposium Series. 24. 37-39 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Nishino, Y.Nagato, Y.Hasegawa, H.Yamamoto, K.Kamaike, and Y.Ishido: "Efficient Deanilidation of Physphroanilidates by the Use of Nitrites and Acetic Anhydride" Heteroatom Chem.2. 187-196 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kamaike, T.Ogawa, Y.Inoue, and Y.Ishido: "Further Improvement in the Procedure for Oligonucleotide Synthesis in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleosides & Nucleotides. 11. 637-668 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] E,Kawashima, T.Sekine, Y.Aoyama, M.Miyahara, I.Hirao, M.Kainosho, Y.Kyogoku, and Y.Ishido: "Highly Stereoserective Syntheses of (2'R)-[2'-^2H]-2'-Deoxy-ribonucleosides and Synthesis of their Oligonucleotides" Nucleic Acids Synopsium Series. 27. 81-82 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kamaike, T.Ogawa, and Y.Ishido: "Synthesis of an Oligonucleotide Bearing a Phosphate Function at the 5'-Terminus Using a Novel Protecting Group in Terms of a Cellulose Acetate Derivative as a Polymer-support" Nucleosides & nucleotides. 12. 1015-1032 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] E.Kawashima, Y.Aoyama, T.Sekine, E.Nakamura, M.Kainosho, Y.Kyogoku, and Y.Ishido: "Sonochemmical and Triethylborane-induced Tin Deuteride Reduction for the Highly Stereoserective Synthesis of (2'R)-[2'-^2H]-2'-Deoxy-ribonucleosides from 2'Functionalized Ribonucleosides" Terahedron Lett.34. 1317-1320 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] C.Kojima, Y.Kyogoku, Y.Ishido, E.Kawashima, T.Sekine, I.Hirao, and M.Kainosho: "Precise Analyzes of DNA Structure by NMR" Nucleic Acids Symposium Series. 29. 185-186 (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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