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1996 Fiscal Year Final Research Report Summary

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

Co-Investigator(Kenkyū-buntansha) NAKAHARA Yoshinori  Daiwakasei Kogyo Co., Inc.Research Manager, 研究員
Project Period (FY) 1995 – 1996
Keywordsintracellular signal transduction / inositol phospholipid / enzyme reaction / PI(3,4,5)P_3 / PI(4,5)P_2 / inositol / protecting group / phosphoric acid
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.

  • Research Products

    (22 results)

All Other

All Publications (22 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-03-09  

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