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Development of Fluorescent Reagents for Chirality Recognition Based on π-Electron Interaction

Research Project

Project/Area Number 11440214
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 分離・精製・検出法
Research InstitutionHOKKAIDO UNIVERSITY

Principal Investigator

NAKAMURA Hiroshi  Hokkaido University, Grad. School of Environ. Earth Sci., Prof., 大学院・地球環境科学研究科, 教授 (00117194)

Co-Investigator(Kenkyū-buntansha) MOROZUJNI Tatsuya  Hokkaido University, Grad. School of Sci., Inst., 大学院・理学研究科, 助手 (50271713)
YOSHIDA Noboru  Hokkaido University, Grad. School of Environ. Earth Sci., Asso. Prof., 大学院・地球環境科学研究科, 助教授 (00158461)
TANAKA Shunitz  Hokkaido University, Grad. School of Environ. Earth Sci., Prof., 大学院・地球環境科学研究科, 教授 (30142194)
Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥11,300,000 (Direct Cost: ¥11,300,000)
Fiscal Year 2001: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 2000: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1999: ¥5,700,000 (Direct Cost: ¥5,700,000)
KeywordsMolecular Recognition / Excimer / Fluorescence Spectrum / Crown Ethers / 錯形成 / アルカリ土類金属 / キラリティー
Research Abstract

Development of the reagent with pyrene moieties in the terminal of oligopeptide chain Amino acid[ was selected as a target guest of molecular recognition. A molecular design was carried out as follows: L-Phenylalanine or related molecules were introduced on 1,4-diaminobutane by amide bond. To this compound, naphthalene or pyrene moieties were also introduced. This reagent was expected to form a complex with guest molecule by the hydrogen bonds, and to show a fluorescence change was observed at the complex formation.
However, a little fluorescence change was observed at the complex formation with L- or D- phenylalanine esters.
On the other hand, the ^1H NMR spectra showed the chirality recognition for L- or D- phenylalanine esters.
2. Development of cyclodextrin base reagents
Cyclodextrin was selected as a molecular recognizing moiety, and naphthalene group was introduced on the cyclodextrin via methylene chain with several carbon atoms.
This compound (reagent) exhibits a change of fluorescence intensity depending on pH off the aqueous solution, and can be used for a pH sensor.
This reagent also shows a fluorescence change at the complex formation with guest molecules such as (-)borneol or 1-adamentanol. Induced circular Dichroism of this reagent by the guest molecules shows the usefulness for the chirality recognition.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] Hideki Kuramitz: "Electrochemical Evaluation of Interaction between Avidin and Biotin Self-assembled Using Marker Ions"Chem. Lett.. 725-726 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideki Kuramitz: "Control of Electrocatalytic Oxidation of NADH Using an Interaction between Labeled Biotin with Dopamine and Avidin"J. Electroanal. Chem.. 466. 117-121 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideki Kuramitz: "Electrocatalytic Reduction of Hemoglobin at a Self-Assembled Monolayer Electrode Containing Redox Dye, Nile Blue as an Electron-Transfer Mediator"Anal. Sci.. 15(3). 589-592 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Copper (II)-Assisted Self-assebmly of Bis N, O-Bidentate Schiff Bases : New Blocks for a Double-helical Supramolecular Motif"J. Chem. Soc., Perkin Trans. 2. 975-983 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Induced Circular Dichroism Spectra of α-β-, and γ-Cyclodextrin Complexes with π-Conjugate Compounds. Part2. Chiral Dimer Formation and Polarization Directions of π-π^* Transitions in Some Hydroxyazo Guests Having a Naphthalene Nucleus"J. Chem. Soc., Perkin Trans. 2. 379-386 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Supramolecular Motifs in Metal Complexes of Shiff Bases. Part 5. Zinc(II)-Assisted Self Assembly of Some Bis N, N-and N, O-Bidentate Schiff Bases and Chiral Packing Modes in Solid State"J. Chem. Soc., Perkin Trans. 2. 17-26 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tatsuya Morozumi: "New Fluorescent "Off-On" Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions"J. Phys. Chem.. 105(5). 2923-2931 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Toshiyuki Ito: "Photoinduced Electron Transfer and its Magnetic Field Dependence in Supramolecular Complex of Zinc (II) Tetrapenylporphyrin-Viologen Chain-Linked Compound with 2,3,6-Tri-O-methyl-β-cyclodextrin"Chem. Phys. Lett.. 340(3,4). 308-316 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Toshiyuki Ito: "Magnetic Field Effects on the Lifetimes Triplet Biralicals Photogenerated from Zinc (II) Tetraphenylporphyrin-Viologen Chain-Linked Compounds : Dependence on Spacer Chain Length and Environment"Bull. Chem. Soc. Jpn.. 74(4). 657-665 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Supramolecular Motifs in Metal Complexes of Shiff Bases. Part 6. Topology of Two Types of Self-assembly of N, O-Bidentate Shiff Base Ligands by Copper (II) Ions"J. Chem. Soc., Perkin Trans. 2. 1674-1678 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kazuaki Harata: "Crystal Structures of 6-Deoxy-6-mono-substituted β-Cyclodextrins. Substituent-regurated One-dimensional Arrays of Macrocycles"J. Chem. Soc., Perkin Trans.2. 1667-1673 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tomomi Ujiie: "Rotaxne Type Complexation Behavior of Cyclodextrins with Zinc (II) tetraphenylporphyrin-Viorogen Linked Compounds"J. Inclusion Phenomena and Macrocyclic Chemistry. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideki Kuramitz: "Electrochemical Evaluation of Interaction between Avidin and Biotin Self-assembled Using Market Ions"Chem. Lett.. (8). 725-726 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideki Kuramitz: "Control of Oxidation of NADH Using an Interaction between Labeled Biotin with Dopamine and Avidin"J. Electroanal. Chem.. 466. 117-121 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideki Kuramitz: "Electrocatalytic Reduction of Hemoglobin at a Self-Assembled Electrode Containing Redox Dye, Nile Blue as an Electron-Transfer Mediator"Anal. Sci.. 15(3). 589-592 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Cooper(II)-Assisted Self-assebmly of Bis-N,O-Bidentate Schiff Bases: New Blocks for a Double-helical Supramolecular Motif"J. Chem. Soc. Perkin Trans. 2. 1999. 975-983 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Induced Circular Dichroism Spectra of α- β-, and γ-Cycloaextrin Complexes with π-Conjugate Compounds. Part 2. Chiral Dimer Formation and Polarization Directions of π-π Transitions in Some Hydroxyazo Guests Having a Naphthalene Nucleus"J. Chem. Soc., Perkin Trans. 2. 1999. 379-386 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Supramolecular Motifs in Metal Complexes bf Shiff Bases. Part 5. Zinc(II)-Assisted Self Assembly of Some Bis-N,N- and N,O-Bidentate, Shiff Bases and Chiral Packing Modes in Solid State"J. Chem. Soc., Perkin Trans. 2. 2000. 17-26 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tatsuya Morozumi: "New Fluorescent "Off-On" Behavior of 9-Anthryl Aromatic Amides through Controlling the twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions"J. Phys. Chem.. 105(15). 2923-2931 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Toshiyuki Ito: "Photoinduced Electron Transfer and its Magnetic Field Dependence in Supramolecular Complex of Zinc(II) Tetraphenylporphyrin-Viologen Chain-Linked Compound with 2,3,6-Tri-O-methyl-β-cyclodextrin"Chem. Phys. Lett.. 340(3, 4). 308-316 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Toshiyuki Ito: "Magnetic Field Effects on the Lifetimes Triplet Biradicals Phbtogenerated from Zinc(II) Tetraphenylporphyrin-Viologen Chain-Linked Compounds: Dependence on Spacer Chain Length and Environment"Bull. Chem. Soc. Jpn.. 74(4). 657-665 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Noboru Yoshida: "Supramolecular Motifs in Metal Complexes of Shiff Bases. Part 6. Topology of Two Types of Self-assembly of N,O-Bidentate Shiff Base Logands by Copper(II) Ions"J. Chem. Soc., Perkin Trans. 2. 2001. 1674-1678 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kazuaki Harata: "Crystal Structures of 6-Deoxy-6-mono-substituted β-Cyclodextrins. Substituent-regurated One-dimensional Arrays of Macrocycles"J. Chem. Soc., Perkin Trans. 2. 2001. 1667-1673 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tomomi Ujiie: "Rotaxne Type Complexation Behavior of Cyclodextrins with Zinc(II)tetraphenylporphyrin-Viorogen Linked Compounds"J. Inclusion Phenomena and Macrocyclic Chemistry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tatsuya Morozumi: "New Fluorescent "Off-On" Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions"J. Phys. Chem.. 105(15). 2923-2931 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Toshiyuki Ito: "Photoinduced Electron Transfer and its Magnetic Field Dependence in Supramolecular Complex of Zinc(II) Tetraphenylporphyrin-Viologen Chain-Linked Compound with 2,3,6-Tri-O-methyl-β-cyclodextrin"Chem. Phys. Lett.. 340(3,4). 308-316 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Toshiyuki Ito: "Magnetic Field Effects on the Lifetimes of Triplet Biradicals Photogenerated from Zinc(II) Tetraphenylporphyrin-Viologen Chain-Linked Compounds : Dependence on Spacer Chain Length and Environment"Bull. Chem. Soc. Jpn.. 74(4). 657-665 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Noboru Yoshida: "Supramolecular Motifs in Metal Complexes of Shiff Bases. Part6. Topology of Two Types of Self-assembly of N,O-Bidentate Shiff Base Ligands by Copper(II) Ions"J. Chem. Soc., Perkin Trans. 2. 2001. 1674-1678 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Kazuaki Harata: "Crystal Structures of 6-Deoxy-6-monosubstituted β-Cyclodextrins. Substituent-regurated One-dimensional Arrays of Macrocycles"J. Chem. Soc., Perkin Trans. 2. 2001. 1667-1673 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tomomi Ujiie: "Rotaxne Type Complexation Behavior of Cyclodextrins with Zinc(II)tetraphenylporphyrin-Viorogen Linked Compounds"J. Inclusion Phenomena and Macrocyclic Chemistry. (印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tatsuya Morozumi: "New Fluorescent "Off-On" Behavior of 9-Anthryl Aromatic Amides through Controlling TICT Relaxation Process by Complexation with Metal Irons"The Journal of Physical Chemistry B. 105(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Toshiyuki Itoh: "Magnetic Field Effects on the Lifetimes of Triplet Biradicals Photogenerated from Zinc (II) Tetraphenylporphyrin-Viologen Chain -Linked Compounds : Dependence on the Spacer Chain Length and Microenvironment."Bulletin of the Chemical Society of Japan. 74(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 中村博: "パソコンによるFT-NMRのデータ処理"三共出版. 112 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 穴田貴久: "アントラセンを末端に有するポリエテール型蛍光試薬の錯形成挙動"分析化学. 48(12). 1107-1114 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Mitsuhiko Morisue: "Molecular Recognition and Monolayer Formation of Azobenzene-Containing Nucleobase Amphiphile Assisted by cis-trans Photoisomerization at Air-Water Interface"Molecular Crystal and Liquid Crystal. 337. 457-460 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hideki Kuramitz: "Electrochemical Evaluation of Interaction between Avidin and Biotin Self-assembled Using Marker Ions"Chemistry Letters. 8. 725-726 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hideki Kuramitz: "Control of Electrocatalytic Oxidation of NADH Using an Interaction between Labeled Biotin with Dopamine and Avidin"Journal of Electroanalytical Chemistry. 466. 117-121 (1999)

    • Related Report
      1999 Annual Research Report

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

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