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Construction of the Systems with Memory of Molecules and Thir Application to Artificial antibody Catalysts

Research Project

Project/Area Number 07458250
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTOKYO INSTITUTE OF TECHNOLOGY

Principal Investigator

UENO Akihiko  Fac.Bioscience & Biotechnology, Professor, 生命理工学部, 教授 (50091658)

Co-Investigator(Kenkyū-buntansha) IKEDA Hiroshi  Fac.Bioscience & Biotechnology, Assist.Prof., 生命理工学部, 助手 (70201910)
NAKAMURA Asao  Fac.Bioscience & Biotechnology, Assist.Prof., 生命理工学部, 助手 (50155818)
IKEDA Tsukasa  Fac.Bioscience & Biotechnology, Assist.Prof., 生命理工学部, 助手 (40151295)
Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1997: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsCyclodextrin / Molecular Memory / Host-Guest / Fluorescence / Crosslinking / Shape Memory / 分子記憶系 / 人工抗体触媒 / 包接錯体 / 分子認識 / 修飾シクロデキストリン
Research Abstract

In this study, attempts have been made to develop a new molecular imprinting method that gives soluble hosts with a memory of size and shape of guest molecules. beta-CycIodextrin (beta-CD), which acts as .a host molecule in aqueous solution, has been used as a key compound to reach the aim. First, to a mixture of 1-naphthaleneacetic acid (template guest) and b-CD were added glutalalic acid chloride, malonyl acid chloride, and succinic acid chloride. The intramolecular crosslinking occurring around the included guest molecule may form the cavity which has a memory of the-size and shape of the guest. After the reaction, insoluble matter was removed by filtration-and the solution was desalted. The solution was added to acetone, and the precipitates were collected. The extents in memory ability were evaluated by obtaing binding constants (1 : 1 stoichiometry) from the changes in the fluorescence intensity induced by addition of the modified CD with memory ability. The guest induced variations in the fluorescence intensity could be analized by 1 : 1 host-guest stoichiometry. The guest selectivities were evaluated by the relative binding vonstants, making 100 for naphthalene as a standard. When I-naphthaleneacetic acid was used as the template guest, l-methoxynaphthalene was bound two-times stronger to the modified CD than to j3-CD itself. On the other hand, when 2-naphihaleneacetic acid was a template guest, 2-methoxynaplithalene and 2-ethoxynaphthalene were bound two times stronger to the modified CD.As another attempt, column chromatography was performed by using template guest bound to column gel and CDs with seven amino or ethylendiamine units. In this case, Scuff s base formation is the crosslinking reaction. This method has been proven to be a promissing method as new molecular imprinting method.

Report

(3 results)
  • 1997 Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 results)

  • [Publications] Shinji Usui: "The Structure of Mono-(3-amino-3-deoxy)-α-cyclodextrin in aqueous sdution-Molecular Dynamics and NMR Studies" J.Molecular Structure. 442. 161-168 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Taiyo Aoyagi: "Synthesis and Photoisomerization of an Azobenzene Derivative Bearing Two β-Cyclodextrin Urits at Borh Ends" Makromol.Chem.Rapid Commun.19. 103-105 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akihiko Ueno: "Guest-responsive Exclmer Fluorescence of β-Cyclodextrin Bearing a Pendant with two Pyrene Moieties" Makromol.Chom.Rapld Commun.19. 103-105 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Seiji Sakamoto: "Molecular Assembly of Two-α-helix Peptide Induced by Haem Binding" Chem.Commun.1073-1074 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kakio Tamura: "Encrgg Transfer in a Rotaxane with a Naphthalene-modified α-Cyclodextrin Threaded by pansyl-terminated PEG" Chem.Lett.369-370 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Sanyo Hamai: "H-NMR Investigation of the Binding of 2-Methyenapnthalene to α-Cyclodextrin in P_2O solutions" J.of Inclusion Phenomena and Molecular Recognition in Chemistry. 31. 265-273 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akihiko Ueno: "Fluorescent Cydodextrins Responsive to Molecules and Metal Ions." J.Org.Chem.64. 382-387 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Nakamura, T.Imai, S.Okatsu, Y.Oda, A.Ueno, and F.Toda: "Long-Range Triplet-Triplet Energy Transfer in Supramolecular Species in Fluid Aqueous Solutions." Chem.Lett.313-314 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Nakamura, T.Ikeda, A.Nakamura, H.Ikeda, A.Ueno, and F.Toda: "Remarkable Molecular Recognition of Dansyl-Modified Cyclodextrin Dimer." Chem.Lett.343-344 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Nakamura, A.Ikeda, N.Ise, T.Ikeda, H.Ikeda, F.Toda, and A.Ueno: "Dansyl-Modified beta-Cyclodextrin with a Monensin Residue as a Hydrophobic Metal Responsive Cap." Chem.Lett.721-722 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Nakamura, S.Sato, K.Hamasaki, A.Ueno, and F.Toda: "Association of 1 : 1 Inclusion Complexes of Cyclodextrins into Homo-and Heterodimers : A Spectroscopic Study Using a TICT-Forming Fluorescence Probe as a Guest Compound." J.Phys.Chem.99. 10952-10959 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] F.Hamada, K.Ishikawa, I.Tamura, and A.Ueno: "Molecular-Recognition and Sensory System of gamma-Cyclodextrin Capped by Sodium Anthranilate." Anal.Sci.11. 935-939 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hamasaki and A.Ueno: "Significant Enantioselectivity in Alanine Ester Hydrolysis Catalyzed by Imidazole Attached beta-Cyclodextrin." Chem.Lett.859-860 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] J.Wang, A.Nakamura, K.Hamasaki, H.Ikeda, T.Ikeda, and A.Ueno: "A Fluorescent Molecule-Recognition Sensor with a Protein as a Environmental Factor." Chem.Lett.303-304 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Kuwabara, A.Nakamura, T.Ikeda, H.Ikeda, A.Ueno, and F.Toda: "Supramolccular Asscmbly of Dyc-Modified Cyclodextrin Formed by Inclusion of its Dye-Part in Native Cyclodextrin." Supramolecular Chem.303-304 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Ueno: "Fluorescent Cyclodextrins for Molecule sensing." Supramolecular Sci.3. 31-36 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Kuwabara, M.Takamura, A.Matsushita, A.Ueno, and F.Toda: "A Novel Color-Changeable Host for Molecules. Guest-induced Colorless-to-Color Chang of Phenolphthalein-modified beta-Cyclodextrin. Chem.Lett., 2081-2084 (1996)" Supramolecular Chem.303-304 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Keita Hamasaki: "Significant Enantioselectivity in Alanine Ester Hydrolysis Catalyzed by Imidazole Attached β-Cyclodextrin" Chem.Lett.859-860 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tetsuo Kuwabara: "Supramolecular Assembly of Dye-Modified Cyclodextrin Formed by Inclusion of its Dye-Part in Native Cyclodextrin" Supramolecular Chem.7. 235-238 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tetsuo Kuwabara: "A Novel Color-Changeable Host for Molecules.Guest-induced Color-to-color Change of Phenolphthalein-modified β-Cyclodextrin" Supramolecular Chem.8. 13-15 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuaki Harata: "Crystal Structure of mono(3-amino-3-decxy)-α-Cyclodextrin.5.5hydrate.Evidence for the ^<3,0>β Boat Conformation of the Altrosamine reridue" J.Chem,Soc.,Chem.Commun.,. 2347-2348 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hiroshi Ikeda: "Fluorescent Cylodextrins for Molecule Sensing.Fluorescent Proportics,NMR Characterization,and Inclusion Phenomena of N-Dansylleucine Cyclodextrin" J.Am.Chem.Soc.,. 118. 10980-10988 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Fumio Hamada: "Photochromic Molecular Recognition of β-Cyclodextrin Bearing Spiropyran Moiety for Organic Guests" J.Chem.Soc,Rerkin Trans.2. 2567-2570 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Akihiko Ueno: "Comprehensive Supramolecular Chemistry(分担)Vol.3" Pergamon, 132 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 上野昭彦: "蛋白質 核酸 酵素(センサーフクノロジー2部分)" 共立出版, 8 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Asao Nakamura: "Long-Range Triplet-Triplet Energy Transfer in Supranolecular Species in Fluid Aquecus Solutions" Chem. Lett.313-314 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Michiei Nakamura: "Remarkable Molecular Recognition of Dansyl-Modified Cyclodetrin Dimer" Chem. Lett.343-344 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Michiei Nakamura: "Dansyl-Modified β-Cyclodextrin with a Monensin Residue as a Hydrophobic, Metal Responsive Cap" J. Chem. Soc., Chem. Commun.721-722 (1955)

    • Related Report
      1995 Annual Research Report
  • [Publications] Asao Nakamura: "Association of 1:1 Inclusion Complexes of Cyclodextrins into Homo-and Hetero dimers: A pectroscopic Study Using a TICT-Forming Fluorescent Probe as a Guest" J. Phys. Chem.99. 10952-10959 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Fumio Hamada: "Spacer Effect of Appended Moieties for Molecular Recognition in Doubly-Sodium Anthranilate Modified γ-Cyclodextrin" J. Inclusion. Phenom.20. 43-51 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Fumio Hamada: "Molecular-Recognition and Sensory System of γ-Cyclodextrin Capped by Sodium Anthranilate." Anal. Sci.11. 935-939 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Juan Wang: "Chem. Lett." A Fluorescent Molecule-Recognition Sensor with a Protein as a Environmental Factor(印刷中), (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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