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Preparation of Inositol Derivatives

Research Project

Project/Area Number 07554030
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section試験
Research Field Organic chemistry
Research InstitutionEhime University

Principal Investigator

KOGA Masakazu (1996)  Ehime University, Department of Applied Chemistry Assistant Professor, 工学部, 助手 (70263960)

尾崎 庄一郎 (1995)  愛媛大学, 工学部, 教授 (80145060)

Co-Investigator(Kenkyū-buntansha) NAKAHARA Yoshinori  Daiwakasei Kogyo Co., Inc.Research Manager, 研究員
古賀 理和  愛媛大学, 工学部, 助手 (70263960)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥6,000,000 (Direct Cost: ¥6,000,000)
Fiscal Year 1996: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1995: ¥3,000,000 (Direct Cost: ¥3,000,000)
Keywordsintracellular signal transduction / inositol phospholipid / enzyme reaction / PI(3,4,5)P_3 / PI(4,5)P_2 / inositol / protecting group / phosphoric acid / ミオイノシトール / ミオイノシトール三リン酸 / 酵素 / リン酸化
Research Abstract

Recently, inositol phospholipids in the plasma membrane have received much attention due to their biological interests in signal transduction systems. These lipids and their metabolic products are required to be provided chemically to investigate a variety of biological processes including metabolism of inositol phosphates. For the purposes, some efficient synthetic methodologies have been developed and used to synthesize inositol phosphate derivatives. The results obtained in this project are described individually as follows.
1.Optically active inositol derivatives such as D- and L-1,2-cyclohexylidene-myo-inositol could be efficiently prepared by enzymatic reactions. They were used for the synthesis of several inositol polyphosphates.
2.Several covalently liked hybrid molecules between vitamin C and inositol derivatives were prepared in large scale and estimated to be effective for stabilization of the vitamin.
3.Some phosphatidylinositol 3,4,5-trisphosphates (PIP_3) with saturated fatty acid chains were synthesized and proved to activate PKC.
4.Phosphatidylinositol 4,5-bisphosphate (PIP_2) with saturated fatty acid chains were prepared, using the new protecting group, PAC and selective phosphorylation method based on the phosphite chemistry.
5.A regiospecific synthesis of phosphatidylinositol-2,6-dimannoside (PIM_2) has been accomplished by using glycosylation of mannopyranosyl phosphite.
6.A new protecting groups for alcohol and phosphate were developed and by using them, unsaturated-type phosphatidylinositol phosphates could be synthesized.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] Shoichiro Ozaki: "Enzymatic Resolution of the Sterically Hindered myo-Inositol Derivative" Bull.Chem.Soc.Jpn.68・4. 1200-1205 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of 1D-Distearoylphosphatidyl-myo-Inositol 3,4,5-Tris-(dihydrogen phosphate)" Tetrahedron. 51・33. 8969-8976 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Regiospecific Synthesis of 2,6-Di-O-α-D-mannopyranosyl-phosphatidyl-D-myo-inositol" J.Org.Chem.61・1. 14-15 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shigeharu Moriya: "Platelet-derived Growth Factor Activates Protein Kinase Cε through Redundant and Independent Signaling Pathways Involving Phospholipase Cγ or Phosphatidylinositol 3-Kinase" Proc.Nat.Acad.Sci.USA,. 93・1. 151-155 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Kazuo Morisaki: "Synthesis of Novel Vitamin C Phosphodiesters: Stablility and Antioxidant Activity" Carbohydr.Res.286. 123-138 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Takashi Kanematsu: "A New Inositol 1,4,5-Trisphosphate Binding Protein Similar to Phospholipase Cδ1" Biochem.J.313. 319-325 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Kazuo Morisaki: "Design of Novel Hybrid Vitamin C Derivatives: Thermal Stability and Biological Activity" Chem.Pharm.Bull.44・9. 1647-1655 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of Phosphorofluoridate Analogues of myo-Inositol 1,4,5-Tris(phosphate)and their Biological Activity" J.Chem.Soc.,Chem.Commun.15. 1815-1816 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hiroshi Takeuchi: "Localization of Binding Domain and its Specificity of a New Inositol 1,4,5-Trisphosphate Binding Protein which Carries a Pleckstrin Homology Domain" Biochem.J.318. 561-568 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of 2,6-Di-O-α-D-mannopyranosylphosphatidyl-D-myo-inositol.Utillization of Glycosylation and Phosphorylation based on Phosphite Chemistry" Tetrahedron. 53・3. 903-918 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Lei Ling: "Chemoenzymatic Synthesis of Optically Active myo-Inositol Polyphosphates in Carbohydrate in Drugs" Marcel Dekker Inc., 43 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shoichiro Ozaki: "Enzymatic Resolution of the Sterically Hindered myo-Inositol Derivative" Bull.Chem.Soc.Jpn. 68(4). 1200-1205 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of 1D-Distearoylphosphatidyl-myo-Inositol 3,4,5-Tris- (dihydrogen phosphate)" Tetrahedron. 51(33). 8969-8976 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Regiospecific Synthesis of 2,6-Di-OMICRON-alpha-D-mannopyranosylphosphatidyl-D-myo-inositol" J.Org.Chem.61(1). 14-15 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shigeharu Moriya: "Platelet-derived Growth Factor Activates Protein Kinase Cepsilon through Redundant and Independent Signaling Pathways Involving Phospholipase Cgamma or Phosphatidylinositol 3-Kinase" Proc.Nat.Acad.Sci.USA. 93(1). 151-155 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Kazuo Morisaki: "Synthesis of Novel Vitamin C Phosphodiesters : Stablility and Antioxidant Activity" Carbohydr.Res.286. 123-138 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Takashi Kanematsu: "A New Inositol 1,4,5-Trisphosphate Binding Protein Similar to Phospholipase Cdelta_1" Biochem.J.313. 319-325 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Kazuo Morisaki: "Design of Novel Hybrid Vitamin C Derivatives : Thermal Stability and Biological Activity" Chem.Pharm.Bull.44(9). 1647-1655 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of Phosphorofluoridate Analogues of myo-Inositol 1,4,5-Tris (phosphate) and their Biological Activity" J.Chem.Soc., Chem.Commun.(15). 1815-1816 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hiroshi Takeuchi: "Localization of Binding Domain and its Specificity of a New Inositol 1,4,5-Tris-phosphate Binding Protein which Carries a Pleckstrin Homology Domain" Biochem.J.318. 561-568 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yutaka Watanabe: "Synthesis of 2,6-Di-OMICRON-alpha-D-mannopyranosyl-phosphatidyl-D-myo-inositol. Utilization of Glycosylation and Phosphorylation based on Phosphite Chemistry" Tetrahedron. 53(3). 903-918 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Lei Ling: "Chemoenzymatic Synthesis of Optically Active myo-Inositol Polyphosphates in "Carbohydrate in Drugs"" Marcel Dekker Inc.43 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shoichiro Ozaki: "Enzymatic Resolution of the Sterically Hindered myo-Inositol Derivative" Bull.Chem.Soc.Jpn.68・4. 1200-1205 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yutaka Watanabe: "Synthesis of 1D-Distearoylphosphatidyl-myo-Inositol 3,4,5-Tris-(dihydrogen phosphate)" Tetrahedron. 51・33. 8969-8976 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yutaka Watanabe: "Regiospecific Synthesis of 2,6-Di-Ο-α-D-mannopyranosyl-phosphatidyl-D-myo-inositol" J.Org.Chem.61・1. 14-15 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shigeharu Moriya: "Platelet-derived Growth Factor Activates Protein Kinase Cε through Redundant and Independent Signaling Pathways Involving Phospholipase Cγ or Phosphatidylinositol 3-Kinase" Proc.Nat.Acad.Sci.USA,. 94・1. 151-155 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuo Morisaki: "Synthesis of Novel Vitamin C Phosphodiesters : Stablility and Antioxidant Activity" Carbohydr.Res.286. 123-138 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Takashi Kanematsu: "A New Inositol 1,4,5-Trisphosphate Binding Protein Similar to Phospholipase Cδ_1" Biochem.J.313. 319-325 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuo Morisaki: "Design of Novel Hybrid Vitamin C Derivatives : Thermal Stability and Biological Activity" Chem.Pharm.Bull.44・9. 1647-1655 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yutaka Watanabe: "Synthesis of Phosphorofluoridate Analogues of myo-Inositol 1,4,5-Tris(phosphate)and their Biological Activity" J.Chem.Soc.,Chem.Commun.15. 1815-1816 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hiroshi Takeuchi: "Localization of Binding Domain and its Specificity of a New Inositol 1,4,5-Trisphosphate Binding Protein which Carries a Pleckstrin Homology Domain" Biochem.J.318. 561-568 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yutaka Watanabe: "Synthesis of 2,6-Di-Ο-α-D-mannopyranosylphosphatidyl-D-myo-inositol. Utilization of Glycosylation and Phosphorylation based on Phosphite Chemistry" Tetrahedron. 53・3. 903-918 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Lei Ling: "Chemoenzymatic Synthesis of Optically Active myo-Inositol Polyphosphates in Carbohydrate in Drugs" Marcel Dekker Inc., 43 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] L. Ling and S. Ozaki: "Enzymatic resolution of sterically hindered inositol derivative." Bull. Chem. Soc. Jpn.68. 1200-1205 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y. Watanabe, M. Tomioka S. Ozaki: "Synthesis of 1-D-distearoyl phophatidyl-myo-inositol 3,4,5-tris(dihydrogen phosphate)" Tetrahedron. 51. 8969-8976 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Hirata, Y. Watanabe, T. Kanematsu, S. Ozaki, T. Koga: "D-myo-inositol 1,4,5-trisphosphate analoges substituted at the 3-hydroxyl group" Biochem. Biophy. Acta.1244. 404-410 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Ozaki and L. Ley.: "Carbohydrate in Drugs. Chemoenzymatic Synthesis of Optically Active myo-Inositol Polyphosphates." Marcel Dekker Inc., 43 (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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