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Development of New Chiral Packing Material for HPLC Based on the Structure Control of Polysaccharide Derivatives and Their Immobilization onto Silica Gel

Research Project

Project/Area Number 13355033
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 高分子合成
Research InstitutionNagoya University

Principal Investigator

OKAMOTO Yoshio  Nagoya Univ., Grad.School of Eng., Professor, 工学研究科, 教授 (60029501)

Co-Investigator(Kenkyū-buntansha) TACHIBANA Kozo  Daicel Chemical industries, LTD., Tsukuba Research Center, Research Scientist, 筑波研究所, 研究員
YAMAMOTO Chiyo  Nagoya Univ., Grad.School of Eng., Assistant Professor, 工学研究科, 助手 (80314045)
HABAUE Shigeki  Yamagata Univ., School of Eng., Professor, 工学部, 助教授 (30252266)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥41,600,000 (Direct Cost: ¥32,000,000、Indirect Cost: ¥9,600,000)
Fiscal Year 2003: ¥10,270,000 (Direct Cost: ¥7,900,000、Indirect Cost: ¥2,370,000)
Fiscal Year 2002: ¥11,700,000 (Direct Cost: ¥9,000,000、Indirect Cost: ¥2,700,000)
Fiscal Year 2001: ¥19,630,000 (Direct Cost: ¥15,100,000、Indirect Cost: ¥4,530,000)
KeywordsPolysaccharide Derivatives / HPLC / Enantioseparation / Immobilization / Chiral Packing Material / Radical Polymerization / Chiral Recognition / Chiral Stationary Phase / ジメチルブタジエン / 共重合 / スチレン
Research Abstract

Phenylcarbamate derivatives of cellulose and amylose are known to show high chiral recognition as chiral stationary phases (CSPs) in HPLC. However, the solvents such as chloroform and tetrahydrofuran, which dissolve or swell the polysacoharide derivatives, cannot be used as main mobile phases for the CSPs. In order to overcome this defect, the cellulose 3,5-dimethylphenylcarbamate derivative having a regioselective vinyl group was immobilized to silica gel via the radical copolymerization with vinyl monomer under various immobilization conditions.
・When the content of the vinyl monomer was low, the chiral recognition abilities of the obtained CSPs were similar to those of the coated CSP.
・The immobilization was attained more effectively by using silica gel having a vinyl group.
・Cellulose derivative having a random vinyl group at the 2-, 3-, and 6-positions were prepared by the one-pot process to avoid the complicated synthetic process. The obtained derivative was quantitatively immobilized on silica gel as well as the cellulose derivatives having the regioselective vinyl group.
・When the cellulose derivative having a vinyl group was copolymerized with 2,3-dimethylbutadiene, the chiral recognition ability of the immobilized CSP was close to those of the coated CSP.
This immobilization method was effective for other phenylcarbamate derivatives of cellulose and amylose, indicating that it must be valuable for the preparation of the polysaccharide-based packing materials for the next generation.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (34 results)

All Other

All Publications (34 results)

  • [Publications] T.Kubota, T.Kusano, C.Yamamoto, E.Yashima, Y.Okamoto: "Cellulose 3,5-Dimethylphenylcarbamate Immobilized onto Silica Gel via Copolymerization with a Vinyl Monomer and Its Chiral Recognition Ability as a Chiral Stationary Phase for HPLC"Chem.Lett.. 724-725 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Wakita, B.Chankvetadze, C.Yamamoto, Y.Okamoto: "Chromatographic Enantioseparation on a Wall-coated Open Tubular Capillary Column Containing Covalently Bound Cellulose (3,5-dichlorophenylcarbamate) as Chiral Selector"J.Sep.Sci.. 25. 167-169 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] B.Chankvetadze, C.Yamamoto, Y.Okamoto: "Very Fast Enantioseparation in High-Performance Liquid Chromatography Using Cellulose Tris (3,5-dimethylphenylcarbamate) Coated on Monolithic Silica Support"Chem.Lett.. 32. 850-851 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kubota, C.Yamamoto, Y.Okamoto: "Preparation and Chiral Recognition Ability of Cellulose 3,5-Dimethyiphenylcarbamate Immobilized on Silica Gel through Radical Polymerization"J.Polym.Sci.,Part A. 41. 3703-3712 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Yamamoto, Y.Okamoto: "Optically Active Polymers for Chiral Separation"Bull.Chem.Soc.Jpn.. 77. 227-257 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, E.Yashima, C.Yamamoto: "Materials-Chirality : Volume 24 of Topics in Stereochemistr (Chapter 3:Optically Active Polymers with Chiral Recognition Ability)"John Wiley & Sons Inc. 53 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kubota, T.Kusano, C.Yamamoto, E.Yashima, Y.Okamoto: "Cellulose 3,5-Dimethylphenylcarbamate Immobilized onto Silica Gel via Copolymerization with a Vinyl Monomer and Its Chiral Recognition Ability as a Chiral Stationary Phase for HPLC"Chem.Lett.. 724-725 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] B.Chankvetadze, C.Yamamoto, Y.Okamoto: "Enantioseparation of selected chiral sulfoxides using polysaccharide-type chiral stationary phases and polar organic polar aqueous-organic and normal-phase eluents"J.Chromatogr.A. 922. 127-137 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Wakita, B.Chankvetadze, C.Yamamoto, Y.Okamoto: "Chromatographic Enantioseparation on a Wall-coated Open Tubular Capillary Column Containing Covalently Bound Cellulose (3,5-dichiorophenylcarbamate) as Chiral Selector."J.Sep.Sci.. 25. 167-169 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kubota, C.Yamamoto, Y.Okamoto: "Chromatographic Enantioseparation by Cycloalkylcarbamate Derivatives of Cellulose and Amylose"Chirality. 14. 372-376 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Yamamoto, E.Yashima, Y.Okamoto: "Structural Analysis of Amylose Tris(3,5-dirnethylphenylcarbamate) by NMR Relevant to Its Chiral Recognition Mechanism in HPLC"J.Am.Chem.Soc.. 124. 12583-12589 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Tsuchida, T.Hasegawa, K.Kobayashi, C.Yamamoto, Y.Okamoto: "Resolution of Enantiomers Using Sugar-Carrying Polyisocyanides as Chiral Stationary Phases for HPLC"Bull.Chem.Soc.Jpn.. 75. 2681-2685 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kubota, C.Yamamoto, Y.Okamoto: "Preparation of Chiral Stationary Phase for HPLC Based on Immobilization of Cellulose 3,5-Dimethylphenylcarbarnate Derivatives on Silica Gel"Chirality. 15. 77-82 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Chankvetadze, C.Yamamoto, Y.Okamoto: "Very Fast Enantioseparation in High-Performance Liquid Chromatography Using Cellulose Tris(3,5-dimethylphenylcarbamate) Coated on Monolithic Silica Support"Chem.Lett.. 32. 850-851 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yamamoto, T.Hayashi, Y.Okamoto: "HPLC Enantioseparation Using Chitin Carbamate Derivatives as Chiral Stationary Phases"J.Chromatogr.A. 1021. 83-91 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kubota, C.Yamamoto, Y.Okamoto: "Reversed-phase Liquid Chromatographic Enantioseparation by Cycloalkylcarboxylates of Cellulose and Amylose"Chirality. 15. 309-313 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yamamoto, Y.Okamoto: "Optically Active Polymers for Chiral Separation"Bull.Chem.Soc.Jpn.. 77. 227-257 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, E.Yashima, C.Yamamoto: "Optically Active Polymers with Chiral Recognition Ability"Materials-Chirality : Volume 24 of Topics in Stereochemistry (John Wile & Sons Inc.). 159-211 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] B.Chankvetadze: "Very Fast Enantioseparation in High-Performance Liquid Chromatography Using Cellulose Tris(3,5-dimethylphenylcarbamate) Coated on Monolithic Silica Support"Chem.Lett.. 32・9. 850-851 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kubota: "Preparation and Chiral Recognition Ability of Cellulose 3,5-Dimethylphenylcarbamate Immobilized on Silica Gel through Radical Polymerization"J.Polym.Sci., Part A. 41. 3703-3712 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Yamamoto: "HPLC Enantioseparation Using Chitin Carbamate Derivatives as Chiral Stationary Phases"J.Chromatogr.A. 1021. 83-91 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Yamamoto: "Optically Active Polymers for Chiral Separation"Bull.Chem.Soc.Jpn. 77・2. 227-257 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kubota: "Phenylcarbamate Derivatives of Cellulose and Amylose Immobilized onto Silica Gel as Chiral Stationary Phases for High-Performance Liquid Chromatography"J.Polym.Sci., Part A. 42(印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Okamoto, et al.: "Optically Active Polymers with Chiral Recognition Ability in "Materials-Chirality : Volume 24 of Topics in Stereochemistry""John Wiley & Sons Inc.. 53 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Yamamoto: "Structural Analysis of Amylose Tris(3,5-Dimethylphenylcarbamate) by NMR Relevant to Its Chiral Recognition Mechanism in HPLC"J.Am.Chem.Soc.. 124・42. 12583-12589 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Kubota: "Preparation of Chiral Stationary Phase for HPLC Based on Immobilization of Cellulose 3,5-Dimethylphenylcarbamate Derivatives on Silica Gel"Chirality. 15. 77-82 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.Tsuchida: "Resolution of Enantiomers Using Sugar-Carrying Polyisocyanides as Chiral Stationary Phases for HPLC"Bull.Chem.Soc.Jpn.. 75・12. 2681-2685 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] B.Chankvetadze: "Comparative Study on the Application of Capillary Liquid Chromatography and Capillary Electrochromatography for Investigation of Enantiomeric Purity of the Contraceptive Drug Levonorgestrel"J.Pharm.Biomed.Anal.. 30. 1897-1906 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Kubota: "Chromtographic Enantioseparation by Cycloalkylcarbamate Derivatives of Cellulose and Amylose"Chirality. 14. 372-376 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Kubota: "Cellulose 3,5-Dimethylphenylcarbamate Immobilized onto Silica Gel via Copolymerization with a Vinyl Monomer and Its Chiral Recognition Ability as a Chiral Stationary Phase for HPLC"Chem.Lett.. 724-725 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] B.Chankvetadze: "Enantioseparation of Selected Chiral Sulfoxides Using Polysaccharide-type Chiral Stationary Phases and Polar Organic, Polar Aqueous-organic and Normal-phase Eluents"J.Chromatogr.A. 922. 127-137 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] B.Chankvetadze: "Comparative Enantioseparation of Selected Chiral Drugs on Four Different Polysaccharide-type Chiral Stationary Phases Using Polar Organic Mobile Phases"J.Pharm.Biomed.Anal.. 27. 467-478 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] L.Chankvetadze: "Enantioseparations in Nonaqueous Capillary Liquid Chromatography and Capillary Electrochromatography Using Cellulose Tris(3,5-dimetylphenylcarbamate) As Chiral Stationary Phase"Electrophoresis. 23. 486-493 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Wakita: "Chromatographic Enantioseparation on a Wall-coated Open Tubular Capillary Column Containing Covalently Bound Cellulose (3,5-Dichlotophenylcarbamate) as Chiral Selector"J.Sep.Sci.. 25. 167-169 (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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