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Development of highly sensitive system for determination of absolute configuration of natural-products by labelling with chiral fluorescent reagents

Research Project

Project/Area Number 11556019
Research Category

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

Allocation TypeSingle-year Grants
Section展開研究
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OHRUI Hiroshi  TOHOKU UNIVERSITY, Graduate school of Agriculturalscience professor, 大学院・農学研究科, 教授 (20100050)

Co-Investigator(Kenkyū-buntansha) WADA Akio  Japan spectroscopic corporation, the first Engineering department Manager(research work), 第一技術部, 部長(研究職)
AKASAKA Kazuaki  TOHOKU UNIVERSITY, Graduate school of Agriculturalscience Assistant professor, 大学院・農学研究科, 助教授 (10201881)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥11,100,000 (Direct Cost: ¥11,100,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1999: ¥8,900,000 (Direct Cost: ¥8,900,000)
Keywordschiral discrimination / on-line HPLC-exciton CD analysis / determination of absolute configuration / methylation analysis of oligosaccharides / methiy-branched carbosylic acid / methy-branched alcohol / 蛍光性糖骨格誘導化試薬 / 遠隔位不斉識別
Research Abstract

We have developed a chiral fluorescent labelling reagent, (S)-2-tert-butyl-2-methyl[-], 3-benzodioxole-4-carboxylic acid(1), and determined. the absolute configurations of ciguatoxin and ganbieric acid by the system to use 1 as a labelling reagent. We have also developed a new Chiral analysis method, on-line-HPLC-exciton-CD method using 1 for the determination of absolute configuration of vicinal diols, amino alochols, and diamines. A new highly sensitive methylation analysis system of oligosaccharides that can determine D, L of monosaccharide by labelling with a newly developed (S)-2-methyl-2-β-naphthyl-1, 3-benzodioxole-4-carboxylic acid(2)was developed, and the absolute configuration of a naturalproduct, polycaevenoside A was determined by the system.
A new chiral flurorescent labelling reagent, (R, R)-and(S, S)-2-(2, 3-anthrac-enecarboximido)cyclohexanol(3), for the descrimimnation of the chirality at the position remote from the derivatizable carboxyl group was developed. and the absolute configurations of a ceramide and a ganglioside were determined by the system using 3.Further, (R, R)- and(S, S)-2-(2, 3-anthracenedicarboximido)cycloh-exane carboxylic acid(4)and 3, 4, 6-tri-O-acetyl-2-deoxy-2-(2, 3-naphthalenedica-roboximido)-β-D-glucopyranosyl bromide(5)for derivatization of chirai alcohols were developed. A system for the. determination of absolute configuration of chiral alchols with chiral center at the position remote from the hydroxy group was developed.

Report

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

    (22 results)

All Other

All Publications (22 results)

  • [Publications] Kazuaki Akasaka,Seliochlro Imalzuml,and Hiroshi Ohrui: "EnantiomerlcSeparation of Branched Fatty Acids Having Chiral Centers Remote From the Carboxyl Group by labelling with Chiral Fluorescent Derivatization Reagents"Enantiomer. 3. 169-174 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Shimizu,Jeoong-Hwana Kim,K.Akasaka and H.Ohrui: "Application of (S) -TBMB Carboxylic Acid-Based On-lineHPLC-Exciton-CD Analysis to Acyclic Vicinal Aicohols and Amino Alcohols"Chirality,. 11. 149-159 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Sato,K.Shimizu,Jeong-Kim,and E.Ami.K.Akasaka,H.Ohrul,and H.Meguro: "Study on the Application of the (S) -2-tert-Buty1-2-methyl-1,3-benzodioxole-4-Carboxylic acid based On-line HPLC-Exciton CD Analysis to Acyclic Vicinal Diols and 1,3-DioIs"Chromatography. 20. 71-80 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Ei'ichi Ami and Hiroshi Ohrui: "Lipase-Catalyzed Kinetic resolution of (±) -trans and cis-2-AzidocycloalkanoIs"Biosci, Biotechnol.Biochem.. 63. 2150-2156 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kazuaki Akasaka and Hiroshi Obrui: "Enantiomeric Separation of Branched Fatty Acids after Conversion withTrans-2-(2,3-Santhra cenedicarbo ximido)cyclohexanol, a Highly Sensitive Chiral Fluorescent Conversion Reagent"Biosci, Biotechnol.Biochem.. 63. 1209-1215 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 赤坂和昭,今泉啓一郎,大類洋: "蛍光不斉誘導体化試薬による分岐脂肪酸の遠隔位不斉識別"分析化学. 48. 1085-1094 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Pu Qian,H.Nanjo,T.Yokoyama,T.M.Suzuki,K.Akasaka,and H.Ohrui: "Chiral molecular patterns of self-assembled ion Pirs composed of (R,S),(S)-16-methyloctadecanoic acid and 4, 4'-bipyridine"Chem.Commun.,. 2021-2022 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Akasaka,S.Shitilyukari S.Matsuoka,M.Murata,H.Meguro,and H.Ohrui: "Absolute Configuration of a Ceramidewith a Novel Branched-Chain Fatty Acid Isolated from the Eplphylic Dinoflagellate, Coolja, monotis,"Biosci.Biotechnol.Biochem.,. 64. 1842-1846 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 赤坂和昭,大類洋: "蛍光試薬"ぶんせき. 11. 678-683 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kazuaki Akasaka, Seiiochlro Imaizumi, and Hiroshi Ohrui: "EnantiomericSeparation of Branched Fatty Acids Having Chiral Centers Remote From the Carboxyl Group by labelling with Chiral Fluorescent Derivatization Reagents"Enantiomer. 3. 169-174 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kumi Shimizu, Jeoong-Hwan Kim, Kazuaki Akasaka and Hiroshi Ourui: "Application of(S)-TBMB Carboxylic Acid-Based On-lineHPLC-Exciton-CD Analysis to Acyclic Vicinal Aicohols and Amino Alcohols"Chirality. 11. 149-159 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Syn-ichi Sato, Kumi Shimizu, Jeong-Kim, and Eiichi Ami, Kazuaki Akasaka, Hiroshi Ohrui, and Hiroshi: "Study on the Application of the(S)-2-tert-Butyl-2-methyl-1, 3-benzodioxole-4-Carboxylic acid based On-line HPLC-Exciton CD Analysis to Acyclic Vicinal Diols and 1, 3-Diols"Chromatography. 20. 71-80 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Ei' ichi Ami and Hiroshi Ohrui: "Lipase-Catalyzed Kinetic resolution of(±)-trans and cis-2-Azidocycloalkanols"Biosci, Biotechnol.Biochem.. 63. 2150-2156 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kazuaki Akasaka, Keiichiro Imaizumi, and Hiroshi Ohrui: "Enantiomeric Separation of Branched Fatty Acids having chiral centers remote from the carboxyl group by derivatization with chiral fluorescent-labelling reagents"BUNSEKI KAGAKU. 48. 1085-1094 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Pu Qian, Hiroshi Nanjo, Toshiro Yokoyama, Toshishige M.Suzuki, Kazuaki Akasaka, and Hiroshi Ohrui: "Chiral molecular patterns of self-assembled ion Pirs composed of(R, S), (S)-16-methyloctadecanoic acid and 4, 4'-bipyridine"Chem.Commun.. 2021-2022 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kazuaki Akasaka, Seiya Shitijyukari Shigeru Matsuoka, Michio Murata, Hiroshi Meguro, and Hiroshi Ohrui: "Absolute Configuration of a Ceramidewith a Novel Branched-Chain Fatty Acid Isolated from the Epiphylic Dinoflagellate, Coolja, monotis"Biosci, Biotechnol.Biochem.. 64. 1842-1846 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kazuaki Akasa, Hiroshi Ohrui: BUNSEKI. 11. 678-683 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Pu Qlan,H.Nanjo,T.Yokoyama,Toshishige M.Suzuke,Kazuaki Akasaka and Hiroshi Ohrui.: "Chiral molecular patterns of self-assembled ion pairs composed of (R,S),(S)-16-methyloctadecanoic acid and 4,4'-bipyridine"Chem.Commun.,. 2021-2022 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kazuaki Akasaka,Seiya Shichllyukari,Shigeru Matsuka,Michio Murata,Hiroshi Meguro,and Hiroshi Ohrui: "Absolute Configuration of a Ceramide with a Novel Branched-chain Fatty Acid Isolated from the Epiphytic Dinoflagellate, Cooliamonotis"64(9). 1842-1846 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Akasaka,H.Ohrui: "Application of (S)-TBMB Carboxylic Acid-Based On-Line HPLC-Exciton CD Analysis to Acyclic Vicinal Alcohols and Amino Alcohols"CHIRALITY. 11. 149-159 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Sato,K.Simizu,Jeong-Hwan Kim,E.Ami,K.Akasaka,H.Orui: "Study On The Application of the (S)-2-tert-Butyl-2-methyl-1,3-benzodioxole-4-carboxylic acidbaced On-line HPLC-Exciton CD Analysis to Acyclic Vicinal Diols And 1,3-Diols"Chromatography. 20. 71-80 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Akasaka,H.Ohrui: "Enatiomeric Separation of Branched Fatty Acids after Conversion with trans-2-(2,3-Anthracenedicarboximido) cyclohexanol, a Highly Sensitive Chiral Fluorescent Conversion Reagent"Biosci. Biotechnol. Biochem.. 63・7. 1209-1215 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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