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Development of Highly Sensitive Analytical Systems to Determine the Absolute Configuration of Chiral Compounds

Research Project

Project/Area Number 03556014
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

MEGURO Hiroshi  Tohoku University, Faculty of Agriculture, Professor, 農学部, 教授 (30005590)

Co-Investigator(Kenkyū-buntansha) SAKAYANAGI Nobuyuki  JASCO Co.Ltd.Section of the 2nd.Manager for Management Techniques, システム1課, 研究員
AKASAKA Kazuaki  Tohoku University, Faculty of Agriculture, Assistant, 農学部, 助手 (10201881)
NISHIDA Yoshihiro  Tohoku University, Faculty of Agriculture, Assistant, 農学部, 助手 (80183896)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥13,800,000 (Direct Cost: ¥13,800,000)
Fiscal Year 1993: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1992: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1991: ¥11,400,000 (Direct Cost: ¥11,400,000)
KeywordsAbsolute configuration / Optical purity / Chirality / Fluorescent reagent / (+)-TBMB carboxylic acid / High performance liquid chromatography / chiral derivatization / D, L-sugar / D, L-amino acid / D, L-glycerol / 発ケイ光性試薬 / 高速液体クロマトグラフィー / 光学活性化合物 / キラルカルボン酸 / キラル誘導体 / 蛍光ラベル / キラル誘導試薬 / 糖 / アミノ酸
Research Abstract

With aims to develop highly sensitive ways to determine the absolute configurations of chiral molecules, new type of chiral derivatizing agents, (+)-TBMB and (+)-TBB carboxylic acids were designed and prepared. The absolute configurations of the former was determined to be (2S) by X-ray analysis of the L-phenylalanie derivative. They were designed to have a CD (circular dichroism) chromophore, isolated Me groups and fluorescent in the bodies which can be effectively used in the CD, NMR and HPLC analyzes to determine the absolute configuration and the optical purity of chiral molecules.
Targets for applying these two reagents were directed to three biomolecules, carbohydrates, amino acids and glycerolipids. The analytical conditions were investigated for the derivatization, purification, separations and detections for each. Consequently, simple and highly sensitive methods were established to analyze the D, L-isomers. For sugars and amino acids, NMR and HPLC were effectively employed in the system. For glycerolipids, circular dichroism (CD) based on exciton chirality way was coupled with HPLC system to build a simultaneous system to determine the absolute configuration and the optical purity. This system was employed in the study on the stereochemistries of lipase-catalyzed hydrolysis of glycerides.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report

Research Products

(21 results)

All Other

All Publications (21 results)

  • [Publications] Y.Nishida et.al.: "Crystal Structure of N-〔(+)-2-t-Butyl-2-methyl-1,3-benzodioxole-4-carbonyl〕-L-phenylalanine Methyl Ester" Analytical Science. 7. 349-350 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Nishida et.al.: "Determination of the absolute configuration of mono saccharides using (+)-or (-)-TBMB COOH and high resolution 'H-n.m.r.spectroscopy." Carbohydrate Research. 218. 63-73 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Nishida et.al.: "(+)-Tert-butyl-1,3-benzodioxole-4-carboxylic acid:Fluorescent Chiral Carboxylic Acid with a 1,3-Benzodioxole Sreleton" Tetrahedron:Asymmetry. 4. 1431-1434 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Uzawa et al.: "Determination of the lipase stereoselectivities using circular dichroism (CD);lipases produce chiral di-0-acylglycerols from achiral tri-0-acylglycerols" Biochimica et Biophysica Acta. 1168. 253-260 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Uzawa et al.: "A Convenient evaluation of the stereoselectivities of lipase-catalyzed hydrolysis of tri-0-acylglycerols on a chiral phase liquid chromatography." Biochimica et Biophysica Acta. 1169. 165-168 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Nishida et al.: "A Highly Sensitive Method to Identify the D,L-Configuration of Monosaccharides based on (-)-TBMB Carboxyic Acid and HPLC" J.Carbohydrate Chemistry. (印刷中). (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshihiro Nishida, Hiroshi Ohrui, Hiroshi Meguro, Chizuko Kabuto: "Crystal Structure of N-[(+)-2-t-Butyl-2-methyl-1, 3-benzodioxole-4-carbonyl]-L-phenylalanine Methyl Ester" Analytical Science. 7. 349-350 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshihiro Nishida, Mariko Kumagai, Akiko Kamiyama, Hiroshi Ohrui, Hiroshi Meguro: "Determination of the absolute configuration of monosaccharides using (+)- or (-)-2-tert-butyl-2-methyl-1, 3-benzodioxole-4-carboxylic acid and high-resolution ^1H-n.m.r. spectroscopy" Carbohydrate Research. 218. 63-73 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshihiro Nishida, Masayuki Abe, Hiroshi Ohrui and Hiroshi Meguro: "(+)-Tert-butyl-1, 3-benzodioxole-4-carboxylic acid : Fluorescent Chiral Carboxylic Acid with a 1, 3-Benzodioxole Skeleton" Tetrahedron : Asymmetry. 4. 1431-1434 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hirotaka Uzawa, Takanori Noguchi, Yoshihiro Nishida, Hiroshi Ohrui, Hiroshi Meguro: "Determination of the lipase stereoselectivities using circular dichroism (CD) ; lipases produce chiral di-O-acylglycerols from achiral tri-O-acylglycerols" Biochimica et Biophysica Acta. 1168. 253-260 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hirotaka Uzawa, Hiroshi Ohrui, Hiroshi Meguro, Tamio Mase, Akito Ichida: "A Convenient evaluation of the stereoselectivity of lipase-catalyzed hydrolysis of tri-O-acylglycerols on a chiral phase liquid chromatography" Biochimica et Biophysica Acta. 1169. 165-168 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshihiro Nishida, Chen Bai, Hiroshi Ohrui and Hiroshi Meguro: "A Highly Sensitive Method to Identify the D, L-Configuration of Monosaccharides based on (-)-TBMB Carboxylic Acid and HPLC" Journal of Carbohydrate Chemistry. (accepted for publication). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Jeon-Hwan Kim, Hirotaka Uzawa, Yoshihiro Nishida, Hiroshi Ohrui, Hiroshi Meguro: "A Highly Sensitive HPLC Method for the Determination of the Absolute Configuration and the Optical Purity of Di-O-acylglycerol Using a Chiral Derivatizing Agent, (S)-(+)-2-tert-Butyl-2-methyl-1, 3-benzodioxole-4-carboxylic acid [(+)-TBMB-COOH]" Journal of Chromatography. (accepted for publication). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshihiro Nishida: "Design of New Chiral Derivatizing Agents for the Determination of Absolute Configurations of Natural Products" Kagaku & Seibutsu (Japanese). 29. 347-650 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hirotaka Uzawa, Hiroshi Ohrui, Hiroshi Meguro: "Developments of Practical Methods to Determine the Absolute Configurations of Chiral Glycerols" Kagaku & Seibutsu (Japanese). 29. 394-398 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Uzawa et al.: "Determination of the Lipase Stereoselectivities using Circular dichroism(CD)" Biochim.Biophys.Acta. 1168. 253-260 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Uzawa et al.: "A Convenient evaluation of the stereo selectivity of lipase-catalyzed hydrolysis of tri-O-acylglycerols" Biochim.Biophys.Acta. 1169. 165-168 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Nishida et al: "(+)-Tert-Butyl-1,3-Benzodioxole-4-Carboxylic Acid:Fluorescent Chiral Carboxylic Acid with a 1,3-Benzodioxole Skeleton" Tetrahedron:Asymmetry. 4. 1431-1434 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Nishida et.al: "A Highly Sensitive Method to Determine the D,L-Configuration of Monosaccharides" J.Carbohydr.Chem.(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] J.H.Kim et al: "A Highly Sensitive HPLC Method for the Determination of the Absolute configuration and the Optical Purity of Di-O Acyl Glycerd" J.Chromatography. (印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshihiro Nishida: "Determination of the Absolate Configuration of monosaccharicles Wing (+)or(-)2-tert-butyl-2methyl-1.3-benzodioxole-4-Carloxpylie Acid and Nigh-xeselution ^1H-n.m.r.Spectnoscopy" Carlohyarate Research. 218. 63-73 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-03-31   Modified: 2016-04-21  

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