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Generation of Biomembrane Functions in Organic Solvents and Its Application

Research Project

Project/Area Number 10680571
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionGraduate School of Science & Technology, Kumamoto University

Principal Investigator

IHARA Hirotaka  Kumamoto University, Graduate School of Science & Technology, Professor, 大学院・自然科学研究科, 教授 (10151648)

Co-Investigator(Kenkyū-buntansha) SAGAWA Takashi  Kumamoto University, Department of Applied Chemistry & Biochemistry, Assistant Professor, 工学部, 助手 (20225832)
Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1999: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1998: ¥2,500,000 (Direct Cost: ¥2,500,000)
Keywordsbilayer / gel / amphiphilic property / molecular aggregation / amino acid / optical activity / 両親媒性
Research Abstract

L-glutamic acid-derived lipids were synthesized in order to study the aggregation structures in organic solvents and discussed the driving force for aggregation.
a) Triamide-containing lipids derived from L-glutamic acid produced organic gels through formation of lipid aggregation by hydrogen bonding interaction among the amide moieties. This gelation was formed in various organic solution such as methanol, ethanol, benzene, tetrahydrofuran, toluene and cyclohexane.
b) TEM observation showed that the xerogel after freeze-dried from the clear gel was constructed from a network of microfibrous aggregates. But no similar network was observed at the low concentration (in the sol state) while fragmental microfibers were detectable. It was confirmed that critical gelation (cgc) depended on the kind of organic solvents. For example, the cgc lies between 1 and 0.1 mM at room temperature in benzene. However, SEM and TEM observations showed that fibrous aggregates were produced at lower concentrat … More ion such as 0.01 mM than cgc. This shows that the cgc doesn't agree with the critical aggregation concentration (cac). Therefore, the gel formation is attributed to the development of fibrous aggregates and subsequent formation of an aggregate network.
c) To estimate cac and the aggregation structure, we synthesized new lipids having pyrenyl head group. By fluorescence emission spectra showed that the lipids produced excimers at the concentration above cac.
d) We synthesized triamide-containing L-glutamic acid lipid with tetraalkyl groups and a protoporphyrin IX-head group. The lipid produced highly-oriented fibrous aggregates in organic solution such as benzene, cyclohexane and so on. UV-vis spectra indicated formation of a Soret band which was estimated by red shift phenomena, but these were lost by addition of trifuluoroacetic acid (TFA ) to provide spectra corresponding to those in monomeric dispersion states. CD spectra showed that the aggregates induced positive Cotton effect but addition of TFA reduced the elipticity. These results indicate that hydrogen bonding work as a driving force for aggregation and the cofacial packed-porphyrin planar structure will be included. Less

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] H. Ihara, et al.: "Functional Organic Gel: Excimer Formation through Lipid membrane-Like molecular Orientation in Benzene and Cyclohexane"Abstract of 5th Australia/Japan Symposium on Self-assembly in Colloid Science. Vol. 5. 176 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ihara, et al.: "Enantioselective Elution from Chiral Organic Gels with L-Glutamic Acid-Derived Lipids"Abstract of 10th International Symposium on Chiral Discrimination. Vol. 10. P012 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ihara, et al.: "Highly oriented Chiral porphyrin Fibers Linked by L-Glutamic Acid Groups"Abstract of 11th International Symposium on Chiral Discrimination. Vol. 11. 38 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ihara, et al.: "Supramolecular assembries from amphilic oligomers with amino acid derived terminal groups"Recent Research Developments in Pure & Applied Chemistry. Vol. 2. 59-81 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ihara, et al.: "Detection of highly-oriented Aggregation of L-Glutamic Acid-Derived Lipids in Organic Solution"Liquid Crystals. Vol. 26. 1021-1027 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Hachisako, Y. Murata, H. Ihara: "Supramolecular receptors from alpha-amino acid derivatives"Journal of the Chemical Society, Parkin Transactions 2. 2569-2577 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara, et al.: "Functional Organic Gel: Excimer Formation through Lipid Membrane-Link Molecular Orientation in Benzene and Cyclohexane"Abstract of 5th Australia/Japan Symposium on Self-Assembly in Colloid Science. 5. 176 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara, et al.: "Enantioselective Elution from Chiral Organic Gels with L-Glutamic Acid-Derived Lipids"Abstract of 10th International Symposium on Chiral Discrimination. 10. P012 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara, et al.: "Highly Oriented Chiral Porphyrin Fibers Linked by L-Glutamic Acid Groups"Abstract of 11th International Symposium on Chiral Discrimination. 11. 38 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara, et al.: "Supramolecular assembries from amphiphilic oligomers with amino acid derived terminal groups"Recent Research Developments in Pure & Applied Chemistry. 2. 59 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara, et al.: "Detection of highly-oriented Aggregation of L-Glutamic Acid-Derived Lipids in Organic Solution"Liquid Crystals. 26. 1021 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Hachisako, Y.Murata, H.Ihara: "Supramolecular receptors from alpha-amino acid derivatives"Journal of the Chemical Society, Parkin Transactions. 2. 2569-2577 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Hachisako, H.Nakashima, H.Ihara: "Determination of critical aggregation concentrations of self-assembling lipids in nonpolar organic media using spiropyrans as photochromic probes"Chemistry Letters. 1165-1166 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ihara,et al.: "Functional Organic Gel:Excimer Formation through Lipid Membrane-Like Molecular Orientation in Benzene and Cyclohexane"Abstract of 5 th Australia/Japan Symposium on Self-Assembly in Colloid Science. Vol.5. 176 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ihara,et al.: "Enantioselective Elution from Chiral Organic Gels with L-Glutamic Acid-Derived Lipids"Abstract of 10th International Symposium on Chiral Discrimination. Vol.10. P012 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ihara,et al.: "Highly Oriented Chiral Porphyrin Fibers Linked by L-Glutamic Acid Groups"Abrsract of 11th International symposium on Chiral Discrimination. Vol.11. 38 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ihara,et al.: "Supramolecular assembries from amphiphilic oligomers with amino acid derived terminal groups"Recent Research Developments in Pure&Applied Chemistry. Vol.2. 59-81 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ihara,et al.: "Detection of Highly-oriented Aggregation of L-Glutamic Acid-Derived Lipids in Organic Solution"Liquid Crystals. Vol.26. 1021-1027 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ihara,et al.: "Supramolecular assemblies fromamphiphilic oligomers with amino acid derived terminal groups." Recent Reseorch Developments in Pure & Applied Chemistry. Vol.2. 59-81 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Ihara,et al.: "Detection of highly-oriented aggregation of L-glutamic acid-derived lipids in organic solution." Liquid Crystals. (印刷中).

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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