• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

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
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥9,200,000 (Direct Cost: ¥9,200,000)
Fiscal Year 1994: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1993: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥5,200,000 (Direct Cost: ¥5,200,000)
Keywordsinositolphosphate / inositol-triphosphate / Ca reliese / myoinositol / cellular messenger / membrane permiability / Ins (1,4,5) P_3 / inositol-tetraphosphate / イノシトール五リン酸 / ホスファチジルイノシトール三リン酸 / Z置換基ミオイノシトールポリリン酸 / イノシトール1、4、5三リン酸 / クェブラキトール / ミオイノシトール四リン酸 / ミオイノシトール五リン酸 / 蛍光 / IP_3
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.

Report

(4 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • 1992 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Hirata: "DL-myo-Imositol 1、2、4、5-tetra kisphosphate,a potent amalog of D-myo-Tmositol 1、4、5-triphoshate." Mol pharmacol. 45. 271-276 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ozaki: "Symthesis of 2-Substitufed myo-inositol 1、3、4、5-tetorakisphosphate and 1、3、4、5、6-pentakisphoshate analogs" Bull.Chem.Soc.Jph.67. 1058-1063 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Watanabe: "Synthesi of a phosphatidylinositol 3、4、5-Trisphosphate" Tetrahedron Letters. 35. 123-124 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] L.Ling: "Aconvenient chemoenzymatic synthesis of D-and L-myo-inositol 1、4、5、6-tetra kisphosphate" Carbohydrate Research,in press. 259. 307-310 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hashii: "C^<2+>_a Influx evoked by inositol-3、4、5、6-tetrakisphosphate in ras-trans formed NIH/3TS fibroblasts." FEBS Letters. 340. 276-280 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Yoshidg: "D-myo-Inositol 1、4、5-trisphosphate-binding proteins in rat hrain membranes" J.Biochem. 115. 973-980 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Watanabe: "Phosphonium Salt Methodology for the Synthesis of Phosphoric Monoesters and Diesters and Its Application to Selective Phosphorylation" Tetrahedron Lett.34. 497-500 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] L.Ling: "Enzyme Aided Synthesis of D-myo-Inositol-1,4,5-Trisphosphate" Tetrahedron Lett.34. 2501-2504 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] L.Ling: "Enzymatic Resolution of Racemic 1,2:5,6-di-O-Cyvolohexylidene and 1,2:3,4-di-O-Cyclohexylidene-myo-Inositol" Bioorg.Med.Chem.1. 155-159 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Watanabe: "Absolute Configuration of 4-a-D-Glucopylanosyl-myo-Inositol,Enzymatic Transglycosylation Product" J.Carbohy.Chem.12. 685-692 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Hirata: "Roles for Hydroxyl Groups of D-myo-Inositol-1,4,5-Trisphosphate in the Recongnition by Its Receptor and Metabolic Enzyme" J.Bio.Chem.268. 19260-19266 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Akiyama: "Synthesis of (-)-Conduritol F,(+)-Conduritol B,Cyclophellitol from L-Quebrachitol" Bull.Chem.Soc.Jpn.66. 3760-3763 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] S.Ozaki: "Synthesis and biological properties of 2-substitued myoinositol 1,4,5-trisphosphate and logues directed toward affinity chromatography and photoaffinity labeling" Cabohydrate Res.,. 234. 189-206 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kanematus: "Putative Inositol 1,4,5-Tresphosphate Binding Proteins in Rat Brain Cytoslo." J.Biolog.Chem.,. 267. 6518-6525 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Watanabe: "A new efficient method for resolution of myo-inositol derivatives by enzymi catalyzes regio-and enantio-selective esterifcation in organic solvent" Tetrahedron Lett.,. 33. 1911-1914 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Ozaki: "Synthesis and some prorerties of myo-inositol 1,4,5-tris(dihydrogen phosphate)" J.Chem.Soc.,Perkin Trans.1.729-737 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Akiyama: "A chiral synthesis of D-myo-inositol 1-phosphate starting from L-quebrachitol" Bull.Chem.Soc.Jpn.,. 65. 366-372 (1992)

    • Related Report
      1992 Annual Research Report

URL: 

Published: 1992-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi