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Development of Highly Efficient System for Optical Resolution

Research Project

Project/Area Number 02555184
Research Category

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

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionNagoya University

Principal Investigator

OKAMOTO Yoshio  Nagoya University, Faculty of Engineering, Professor, 工学部, 教授 (60029501)

Co-Investigator(Kenkyū-buntansha) ICHIDA A  Daicel Chemical Co.Research Center, Researcher, 総合研究所, 研究員
INOTSUME N  Kumamoto Univ.Hospital, Lecturer, 医学部付属病院, 講師 (10191892)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥11,700,000 (Direct Cost: ¥11,700,000)
Fiscal Year 1992: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1991: ¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1990: ¥7,900,000 (Direct Cost: ¥7,900,000)
KeywordsOptical resolution / Liquid chromatography / Cellulose / Amylose / Chiral stationary phase / Polyamide / SFC / HPLC / カルバメート / アルコキシフェニルカルバメート / 高速液体クロマトグラフィ- / セルロ-ス / アミロ-ス / カルバメ-ト / 超臨界流体クロマトグラフィ- / セルロ-ナ / 光学性瀬ポリアミド
Research Abstract

1. In order to develop efficient chiral stationary phases for high-performance liquid chromatography to separate optical isomers, various 4-alkoxyphenylcarbamates of cellulose and amylose were prepared and their optical resolving abilities were evaluated after being adsorbed on silica gel. Optical resolving ability depended on the alkoxy group introduced at 4-position, and 4-isopropoxy-, 4-isobutoxy- and 3,5-dimethyl-4-methoxyphenylcarbamates of cellulose were found to afford efficient chiral stationary phases. Various aralkylcarbamates such as benzy1-, 1-phenylethyl-, and 1-phenylpropylcarbamates of cellulose and amylose were also used as chiral stationary phases for HPLC. Among these carbamates, 1-phenylethyl-and 1-phenylpropylcarbamates showed high optical resolving power, and particularly high adility was found on amylose tris ((S)-1-phenylethylcarbamate).
2. Optical resolving abilities of benzoates and phenylcarbamates of cellulose and amylose were tested by supercritical fluid chromatography (FAC). The benzoates were found to show the comparable optical resolving ability to that in HPLC.
3. Optically active polyamides bearing trans-1,2-dicarboxylic acid residue was synthesized and used as chiral stationary phase to evaluate optical resolving ability.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] Y.KAIDA and Y.OKAMOTO: "Efficient Optical Resolution of 4-Hydroxy-2-cyclopentenone Derivatives by HPLC on l-Phenylethylcarbamates of Cellulose and Amylose" Chemistry Letters.85-88 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.KAIDA and Y.OKAMOTO: "Optical Resolution of β-Lactams on l-Phenylethylcarbamates of Cellulose and Amylose" Chirality.4. 122-124 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.KAIDA and Y.OKAMOTO: "Optical Resolution by Supercritical Fluid Chromatography Using Polysaccharide Derivatives as Chiral Stationary Phases" Bull.Chem.Soc.Jpn.,. 65. 2285-2288 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] E.YASHIMA,J.NOGUCHI,and Y.OKAMOTO: "Enantiomer Separation with Cellulose Tris(3,5-dimethylphenylcarbamate)Membrance.Enantioselective Adsorption and Desorption" Chmistry Letters,. 1959-1962 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.KAIDA and Y.OKAMOTO: "The Separaion of Optically Active Copper(1)Catenates" Tetrahedron Letters.34. 1019-1022 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Hargitai,Y.KAIDA,and Y.OKAMOTO: "Preparation and chromatographic evaluation of 3,5-dimethylphenyl carbamoylated β-cyclodextrin stationary phases for normal-phase high-performance liquid chromatographic separation of enantiomers" Journal of Chromatography.628. 11-22 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 岡本 佳男,海田 由里子: "有機合成化学協会誌" 多糖誘導体をキラル固定相に用いる高速液体クロマトグラフィーによる光学分割, 12 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Okamoto, R.Aburatani, and K.Hatada: "Chromatographic Optical Resolution on 3,5-Disubstituted Phenylcarbamates of Cellulose and Amylose" Bull,Chem.Soc.Jpn.63. 955-957 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Okamoto, Y.Kaida, H.Hayashida, and K.Hatada: "Tris(1-phenylethylcarbamate)s of Cellulose and Amylose as Useful Chiral Stationary Phases for Chromatographic Optical Resolution" Chen.Lett.909-912 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] R.Aburatani, Y.Okamoto, and K.Hatada: "Optical Resolving Ability of 3,5-Dimethylphenylcarbamates of Oligosaccharides and Cyclodextrins" Bull.Chem.Soc.Jpn.63. 3603-3610 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Okamoto and Y.Kaida: "Polysaccharide Derivatives as Chiral Stationary Phases in HPLC" J.High Resolut. Chromatogr.13. 706-712 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Okamoto, Y.Nagamura, T.Fukumoto, and K.Hatada: "Chromatographic Optical Resolution of Enantiomers on Polyamides Containing 1,2-Disubstituted Cyclohexane Moiety as a Chiral Residue" Polym.J.23. 1197-1207 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Okamoto, Y.Kaida, R.Aburatani, and K.Hatada: "Chromatographic Optical Resoluton on Polysaccharide Carbamate Phases" ACS Symposium Series 471 "Chiral Separation by Liquid Chromatography" S.Ahuja ed.101-113 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Kaida and Y.Okamoto: "Efficient optical Resolution of 4-Hydroxy-2-cyclopentenone Dervatives by HPLC on 1-Phenylethylcarbamates of Cellulose and Amylose" Chem.Lett.85-88 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Kaida and Y.Okamoto: "Optical Resolution of beta-Lactams on 1-Phenylethylcarbamates of Cellulose and Amylose" Chirality. 4. 122-124 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Kaida and Y.Okamoto: "Optical Resolution by Supercritical Fluid Chromatography Using Polysaccharide Derivatives as Chiral Stationary Phases" Bull.Chem.Soc.,Jpn.65. 2286-2288 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Kaida, Y.Okamoto, J.-C.Chambron, D.K.Mitchell, and J.-P.Sauvage: "The Separation of Optically Active Copper (I) Catenates" Tetrahedron Lett.34. 1019-1022 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Kaida and Y.Okamoto: "Efficient Optical Resolution of 4-Hydroxy-2-cyclopentenone Derivatives by HPLC on 1-Phenylethy carbamates of Cellulose and Amylose" Chemistry Letters,. 85-88 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Kaida and Y.Okamoto: "Optical Resolution of β-Lactams on 1-Phenylethycarbamates of Cellulose and Amylose" Chirality,. 4. 122-124 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Kaida and Y.Okamoto: "Optical Resolution by Supercritical Fluid Chromatography Using Polysaccharide Derivatives as Chiral Stationary Phases" Bull.Chem.Soc.Jpn.,. 65. 2285-2288 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] E.Yashima,J.Noguchi,Y,Okamoto: "Enantiomer Separation with Cellulose Tris(3,5-dimethyphenylcarbamate) Membrance.Enantioselective Adsorption and Desorption" Chmistry Letters,. 1959-1962 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Kaida and Y.Okamoto: "The Separaion of Optically Active Copper(I)Catenates" Tetrahedron Letters,. 34. 1019-1022 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Hargitai,Y.Kaida,and Y.Okamoto: "Preparation and chromatographic evaluation of 3,5-dimethylphenyl carbamoylated β-cyclodextrin stationary phases for normal-phase highperformance liquid chromalographic separation of enatiomers" Journal of Chromatogrophy,. 628. 11-22 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yoshio Okamoto et al.: "Chromatographic Optical Resolution of Enantiomers on Polyamides Containing 1,2-Disubstituted Cyclohexane Moiety as a Chiral Residue" Polymer Journal. 23. 1197-1207 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Peter Knops et al.: "Nitro-und Allyloxy-substituierte helicale [2.2]Metacyclophane:Synthese,Circulardichroismus und Rontgen-Kristallstrukturanalysen" Chem.Ber.124. 1585-1590 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoshio Okamoto et al.: "Chromatographic Optical Resolution on Polysaccharide Carbamate Phases" ACS Symposium Series. 471. 101-113 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yuriko Kaida et al.: "Efficient Optical Resolution of 4-Hydroxy-2-cyclopentenone Derivatives by HPLC on 1-Phenylethylcarbamates of Cellulose and Amylose" Chem.Lett.1992. 85-88 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 岡本 一郎ら: "光学活性高分子を用いた光学異性体分離用液体クロマトグラフィ-カラムの開発" 日本化学会誌. 1992. 133-139 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yuriko Kaida et al.: "Optical Resolution of β-Lactams on 1-Phenylethylcarbamates of Cellulose and Amylose" Chirality. 4. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoshio Okamoto: "Chromatographic optical resolution on 3,5ーdisubatituted phenylcarbamates of cellulose and amylose" Bull.Chem.Soc.Jpn.63. 955-957 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Yoshio Okamoto: "Optical resolution of dihydropyridine enanーtimers by highーperformance liquid chromatoーgraphy using phenylcarbamates of polysacchaーrides as a chiral stationary phase" J.Chromatogr.513. 375-378 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Yoshio Okamoto: "Tris(1ーphenylethylcarbamate)s of cellulose and amylose as useful chiral stationary phase for chromatographic optical resolution" Chem.Lett.909-912 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Ryo Aburatani: "Optical resolving ability of 3,5ーdimethy1ーphenylcarbamates of oligosaccharides and cyclodextrins" Bull.Chem.Soc.Jpn.63. 3606-3610 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Yoshio Okamoto: "Polysaccharide derivatives as chiral stationary phases in HPLC" J.High Resolution Chromatography. 13. 708-712 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Yoshio Okamoto: "Chromatographic optical resolution of enanーtiomers on polyamides consisting of 1,2ーdiーsubstituted cyclohexane moiety" Polymer Journal.

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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