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1994 Fiscal Year Final Research Report Summary

Synthesis of inositol polyphosphate and Derivatives

Research Project

Project/Area Number 04403019
Research Category

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

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

Principal Investigator

OZAKI Shoichiro  Ehime Univ. Fac. Engineering Professor, 工学部, 教授 (80145060)

Project Period (FY) 1992 – 1994
Keywordsinositolphosphate / inositol-triphosphate / Ca reliese / myoinositol / cellular messenger / membrane permiability / Ins (1,4,5) P_3 / inositol-tetraphosphate
Research Abstract

1.Simple synthesis of inositol polyphosphates
Racemic 2,3-O-cyclohexylidene myoinositol was subjected to acetylation with acetic anhydride in the presence of Lipase CES in anhydrous dioxane. The hydroxyl groupe at C-3 position of L-enantiomer was acetylated to give L-1 and unacetylated D-1. D-1 is acetylated with acetic anhydride in DMF at C-6 and C-5 position. These were subjected to phosphorylation and deprotection procedure to afford D-Ins (1,4,5) P3and D-Ins (1,4,6) P3 in high yield. Starting from L-1, D-Ins (1,4,5,6) P4 and D- (1,2,4,5,6) P5 were obtained.
2.Preparation of inositol phosphate affinity column
p-Aminobenzoyl myo inositol derivatives were diazotizedy and then reacted with activated CH-Sepharose. Affinithy column of Ins (1,4,5) P3, Ins (1,3,4) P3, Ins (1,3,4,5) P4 were prepared.
3.Synthesis of membrane permiable Ins Px
In drder to penetrate the molecule through memblrane, minus charge of phosphoric acid must be diminished. Alkyl groups were substituted. But Ca was not released. Substituents must be hydrolized by enzyme in the cell. Protecting groups such as acetoxymethyl, p-acetoxybenzyl, phenoxyethyl are being tried to put on phosphoric acid group. Also large acyl group such palmitoyl is now on trial.
4.Syhthesis of PI (4,5) P2, and PI (3,4) P2 and their affinity column are now in progress.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] L.Ling and S.Ozaki: "Enzyme aided synthesis of D-myo-inositol 1,4,5-trisphosphate." Tetrahedron Lett.34. 2501-2504 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] L.Ling: "Enzymatic resolution of racemic 1,2:5,6-di-O-cyclohexylidene and 1,2:3,4-di-O-cyclohexylidene myo-inositol." Bioorganic and Medicinal Chemistry. 1. 155-159 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Hirata: "DL-myo-Inositol 1,2,4,5-tetrakisphosphate,a potent analog of D-myo-inositol 1,4,5-trisphosphate." Mol.Pharmacol.45. 271-276 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Ozaki: "Synthesis of 2-substituted myo-inositol 1,3,4,5-tetorakis phosphate and 1,3,4,5,6-pentakisphosphate analogs" Bull.Chem.Soc.Jpn.67. 1058-1063 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Watanabe: "Synthesis of a phosphatidylinositol 3,4,5-Trisphosphate" Tetrahedron Letters. 35. 123-124 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Ozaki: "A convenient chemoenzymatic synthesis of D- and L-myo-inositol 1,4,5,6-tetrakisphosphate" Carbohydrate Research. 259. 307-310 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] L.Ling S.Ozaki: "Enzyme aided synthesis of D-myo-inositol 1,4,5-trisphosphate." Tetrahedron Lett.34. 2501-2504 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] L.Ling X.Li Y.Watanabe T.Akiyama S.Ozaki: "Enzymatic resolution of racemic 1,2 : 5,6-di-O-cyclohexylidene and 1,2 : 3,4-di-O-cyclohexylidene myo-inositol." Bioorg. & Med. Chem.1. 155-159 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Hirata N.Narumoto Y.Watanabe T.Kanamatsu T.Koga S.Ozaki: "DL-myo-Inositol 1,2,4,5-tetrakisphosphate, a potent analog of D-myo-inositol 1,4,5-trisphosphate." Mol. Pharmacol.45. 271-276 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Ozaki Y.Koga L.Ling Y.Watanabe Y.Kimura M.Hrata: "Synthesis of 2-substituted myo-inositol 1,3,4,5-tetorakisphosphate and 1,3,4,5,6-pentakis-phosphate analogs" Bull. Chem. Soc. Jpn.67. 1058-1063 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Watanabe eH.Hirofuji S.Ozaki: "Synthesis of a phosphatidylinositol 3,4,5-Trisphosphat" Tetrahedron Lett.35. 123-124 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Ozaki L.Ling T.Ogasawara Y.Watanabe: "A convenient chemoenzymatic synthesis of D-and L-myo-inositol 1,4,5,6-tetrakisphosphate" Carbohydrate Research. 259. 307-310 (1994)

    • 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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