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1997 Fiscal Year Final Research Report Summary

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
KeywordsCyclodextrin / Molecular Memory / Host-Guest / Fluorescence / Crosslinking / Shape Memory
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.

  • Research Products

    (17 results)

All Other

All Publications (17 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-12-08  

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