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DEVELOPMENT OF NEW CHIRAL SURFACTANTS FOR CHIRAL SEPARATION BY MICELLAR ELECTROKINETIC CHROMATOGRAPHY

Research Project

Project/Area Number 10554047
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section展開研究
Research Field 分離・精製・検出法
Research InstitutionHIMEJI INSTITUTE OF TECHNOLOGY

Principal Investigator

TERABE Shigeru  HIMEJI INSTITUTE OF TECHNOLOGY, FACULTY OF SCIENCE, PROFESSOR, 理学部, 教授 (50115888)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Masaki  OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE, TECHNOCHEMISTRY DEPARTMENT, SENIOR RESEARCHER OFFICER, 工業化学課, 研究主任
OIDA Tatsuo  KYOTO INSTITUTE OF TECHNOLOGY, FACULTY OF ENGINEERING AND DESIGN, ASSOCIATE PROFESSOR, 工芸学部, 助教授 (90152032)
OTSUKA Koji  HIMEJI INSTITUTE OF TECHNOLOGY, FACULTY OF SCIENCE, ASSOCIATE PROFESSOR, 理学部, 助教授 (70183762)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥13,800,000 (Direct Cost: ¥13,800,000)
Fiscal Year 2000: ¥2,700,000 (Direct Cost: ¥2,700,000)
Fiscal Year 1999: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1998: ¥8,500,000 (Direct Cost: ¥8,500,000)
KeywordsCAPILLARY ELECTROPHORESIS / MICELLAR ELECTROKINETIC CHROMATOGRAPHY / ENANTIOMER SEPARATION / CHIRAL SURFACTANT / CAPILLARY ELECTROCHROMATOGRAPHY / 硫酸N-デカノイル-N-メチルグルカミドナトリウム
Research Abstract

Three new types of chiral surfactants, tartaric acid derivatives, alkyl glucosides, and alkanoyl glucamides were employed as pseudostationary phases in micellar electrokinetic chromatography for the separation of enantiomers. Among the tartaric acid derivatives, bis (triethylammonium) 2,3-didodecyloxy-1,4-butylene disulfate resolved enantiomers of several PTH-amino acids, antimalarial primaquine, a bronchodilator, procaterol, and a diuretic, indapamide. Sodium dodecyl D-glucopyranoside 6-sulfate and sodium hexadecyl D-glucopyranoside 6-sulfate showed almost equal enantioselectivities resolving several PTH-amino acids. Sodium N-dodecanoyl-N-glucamide was able to resolve enantiomers of both PTH-amino acids and dansyl amino acids, in addition to a muscle relaxant, tolperisone. The surfactant was usable either in acidic or in alkaline conditions. Capillary electrochromatography was applied to enantiomer separation using two different types of columns. A 100 μm i.d. capillary packed with a Daicel OD-type chiral stationary phase and an open tubular capillary of 20 μm i.d. coated with avidin by adsorption were employed. Both columns showed much higher efficiency than the corresponding HPLC columns.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (44 results)

All Other

All Publications (44 results)

  • [Publications] Takuya Tamaguchi: "Simultaneous Separation of Seven Pairs of D,L-Dansylamino Acids by Capillary Electrophoresis with 2,3,6-Tri-O-methyl-β-cyclodextrin in Acidic Media in the Presence or Absence of Surfactants"Chromatography. 19. 15-18 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Effects of Compositions of Dimethyl-β-cyclodextrins on Enantiomer Separations by Cyclodextrin Modified capillary Electrophoresis"Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Separation of Acidic Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique"Journal of Chromatography A. 802. 83-88 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Daisuke Ono: "Synthesis and Properties of Bis (sodium sulfonated ester) Types of Cleavable Surfactants Derived from 1-O-Alkylglycerols"Journal of Surfactants and Detergents. 1. 201-206 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kiichiro Hiyama: "Preparation of Monoalkylphosphate of a Secondary Alcohol"Kagaku to Kogyo. 72. 89-94 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Studies on Enantioselectivities of Avidin, Avidin-Biotin Complex and Streptavidin by Affinity Capillary Electrophoresis"Chromatographia. 49. 489-495 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tatsuo Oida: "Preparation and Properties of Bis-ammonium and Bis-sulfate Gemini Surfactants Derived form Tartaric Acid"Memoirs of the Faculty of Engineering and Design Kyoto Institute of Technology. 48. 31-42 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Separation of Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique with a Chiral Crown Ether"Journal of Chromatography A. 875. 323-330 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Enantiomeric Separation of Drugs by Micellar Electrokinetic Chromatography Using Chiral Surfactants"Journal of Chromatography A. 875. 163-178 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Enantiomer Separations by Capillary Electrochromatography Using Chiral Stationary Phase"Journal of Chromatography A. 887. 457-463 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Daisuke Ono: "Synthesis and Properties of Bis (ammonium bromide) Cleavable surfactants Bearing Two Ester Groups Derived from 1-O-Alkylglycerols"Journal of Japan Oil Chemists'Society. 49. 785-791 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Liu Zhen: "Chiral Separation by Open Tubular Capillary Electrochromatography with Adsorbed Avidin as a Stationary Phase"Journal of Separation Science. 24. 17-26 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Capillary electrochromatographic enantioseparation using a packed capillary with a 3 μm OD-type chiral packing"Journal of Chromatography A. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takuya Yamaguchi: "Simultaneous Separation of Seven Pairs of D,L-Dansylamino Acids by Capillary Electrophoresis with 2,3,6-Tri-O-methyl-β-cyclodextrin in Acidic Media in the Presence or Absence of Surfactants."Chromatography. 19. 15-18 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Effects of Compositions of Dimethyl-β-cyclodextrins on Enantiomer Separations by Cyclodextrin Modified capillary Electrophoresis."Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Separation of Acidic Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique."Journal of Chromatography A.. 802. 83-88 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Daisuke Ono: "Synthesis and Properties of Bis (sodium sulfonated ester) Types of Cleavable Surfactants Derived from 1-O-Alkylglycerols"Journal of Surfactants and Detergents. 1. 201-206 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kiichiro Hiyama: "Preparation of Monoalkylphosphate of a Secondary Alcohol"Kagaku to Kogyo. 72. 89-94 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Studies on Enantioselectivities of Avidin, Avidin-Biotin Complex and Streptavidin by Affinity Capillary Electrophoresis."Chromatographia. 49. 489-495 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tatsuo Oida: "Preparation and Properties of Bis-ammonium and Bis-sulfate Gemini Surfactants Derived form Tartaric Acid."Memoirs of the Faculty of Engineering and Design Kyoto Institute of Technology. 48. 31-42 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yoshihide Tanaka: "Separation of Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique with a Chiral Crown Ether."Journal of Chromatography A. 875. 323-330 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Enantiomer Separations by Capillary Electrochromatography Using Chiral Stationary Phases."Journal of Chromatography A. 887. 457-463 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Otsuka: "Enantiomeric Separation of Drugs by Micellar Electrokinetic Chromatography Using Chiral Surfactants."Journal of Chromatography A. 875. 163-178 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Daisuke Ono: "Synthesis and Properties of Bis (ammonium bromide) Cleavable surfactants Bearing Two Ester Groups Derived from 1-O-Alkylglycerols"Journal of Japan Oil Chemists' Society. 49. 785-791 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Zhen Liu: "Chiral Separation by Open Tubular Capillary Electrochromatography with Adsorbed Avidin as a Stationary Phase."Journal of Separation Science. 24. 17-26 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Koji Kawamura: "Capillary Electrochromatographic Enantioseparation Using a Packed Capillary with a 3 μm OD-type Chiral Packing."Journal of Chromatography A. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takuya Yamaguchi: "Simultaneous separation of seven pairs of D,L-dansylamino acids by capillary electrophoresis with 2,3,6-tri-O-methyl-β-cyclodextrin in acidic media in the presence or absence of surfactants."Chromatography. 19. 15-18 (1998)

    • Related Report
      2000 Annual Research Report
  • [Publications] Koji Otsuka: "Effects of compositions of dimethyl-β-cyclodextrins on enantiomer separations by cyclodextrin modified capillary electrophoresis."Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yoshihide Tanaka: "Studies on enantioselectivities of avidin, avidin-biotin complex and streptavidin by affinity capillary electrophoresis."Chromatographia. 49. 489-495 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] Tatsuo Oida: "Preparation and properties of bis-ammonium and bis-sulfate gemini surfactants derived from tartaric acid."Memoirs of the Faculty of Engineering and Design, Kyoto Institute of Technology. 48. 31-42 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Koji Otsuka: "Enantiomeric separation of drugs by micellar electrokinetic chromatography using chiral surfactants."Journal of Chromatography A. 875. 163-178 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yoshihide Tanaka: "Separation of enantiomers by capillary electrophoresis-mass spectrometry employing a partial filling technique with a chiral crown ether."Journal of Chromatography A. 875. 323-330 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Koji Otsuka: "Enantiomer separations by capillary electrochromatography using chiral stationary phases."Journal of Chromatography A. 887. 457-463 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Zhen Liu: "Chiral separation by open tubular capillary electrochromatography with adsorbed avidin as a stationary phase."Journal of Separation Science. 24. 17-26 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Takuya Yamaguchi: "Simultaneous Separation of Seven Pairs of D,L-Dansylamino Acids by Capillary Electrophoresis with 2,3,6-Tri-O-methyl-β-cyclodextrin in Acidei Media in the Presence or Absence of Surfactants"Chromatography. 19. 15-18 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Koji Otsuka: "Effects of Compositions of Dimethyl-β-cyclodextrins on Enantiomer Separations by Cyclodextrin Modeified capillary Electrophoreses"Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yoshihide Tanaka: "Studies on Enantioselectivities of Avidin,Avidin-Biotin Complex and Streptabidin by Affinity Capillary Electrophoresis"Chromatographia. 49. 489-495 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tatsuo Oida: "Preparation and Properties of Bis-ammonium and Bis-sulfate Gemini Sufactants Derived from Tartaric Acid"Memoirs of the Faculty of Engineering and Design,Kyoto Institute of Technology. 48. 31-42 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Koji Otsuka: "Enantiomer Separation by CEC Using Chiral Stationary Phases"Journal of Chromatography A. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Yoshihide Tanaka: "Separation of Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique with a Chiral Crown Ether"Journal of Chromatography A. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Koji Otsuka: "Enantiomeric Separation of Drugs by Micellar Electorkinetic Chromatography Using Chiral Surfactants"Journal of Chromatography A. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Takuya Yamaguchi: "Simultaneous Separation of Seven Pairs of D,L-Dansylamino Acids by Capillary Electrophoresis with 2,3,6-Tri-O-methyl-β-cyclodextrin in Acidic Media in the Presence or Absence of Surfactants." Chromatography. 19. 15-18 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Koji Otsuka: "Effects of Compositions of Dimethyl-β-cyclodextrins on Enantiomer Separations by Cyclodextrin Modified capillary Electrophoresis." Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshihide Tanaka: "Studies on Enantioselectivities of Avidin,Avidin-Biotin Complex and Streptabidin by Affinity Capillary Electrophoresis." Chromatographia. (印刷中). (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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