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2003 Fiscal Year Final Research Report Summary

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
KeywordsPolysaccharide Derivatives / HPLC / Enantioseparation / Immobilization / Chiral Packing Material / Radical Polymerization / Chiral Recognition / Chiral Stationary Phase
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.

  • Research Products

    (18 results)

All Other

All Publications (18 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2005-04-19  

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