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Chiral HPLC separation with self-assembled organic stationary phase

Research Project

Project/Area Number 13555234
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 工業分析化学
Research InstitutionKyushu University (2003)
Kumamoto University (2001-2002)

Principal Investigator

IHARA Hirotaka  Kyushu University, Inst.Mater.Chem. & Eng., Prof., 先導物質化学研究所, 教授 (10151648)

Co-Investigator(Kenkyū-buntansha) SAKURAI Toshihiko  Kumamoto Univ., Appl.Chem. & Biochem., Assist.Prof., 工学部, 助手 (10332868)
TAKFUJI Makoto  Kumamoto Univ., Appl.Chem. & Biochem., Assist.Prof., 工学部, 助手 (50332086)
石原 晋一郎  (株)興人, 新事業開発部, 主任企画員
永岡 昭二  熊本県工業技術センター, 材料開発部, 主任研究員
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥11,000,000 (Direct Cost: ¥11,000,000)
Fiscal Year 2003: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2002: ¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 2001: ¥4,900,000 (Direct Cost: ¥4,900,000)
KeywordsSelf-assembling systems / Chirality / Enantiomer / Diastereomer / Ordered structure / Liquid chromatography / Polymer grafting / 塩基性ポリマー / グラフトポリマー / 逆相分配 / 液体クロマトグラフィー / 光学活性 / トリプトファン / ダンシル基 / クシ型ポリマー / シリカゲル / 有機-無機ハイブリッド / グルタミン酸 / 分子認識 / 円二色スペクトル
Research Abstract

Chiral separation is still significant target in analytical chemistry and separation technology because each enantiomer provides absolutely different action in biosystems. HPLC with chiral stationary phase has been recognized as a facile method to perform it. However, there are few examples those were accomplished with a reversed phase-HPLC mode as the most convenient HPLC. This is due to no hydrophobicity difference in each enantiomer. Therefore, we focused on self-assembled systems to enhance microenvironmental effect in molecular recognition and applied these systems for functional organic stationary phases. Our research project clarified that (1)poly(octadecyl acrylate)-grafted silica showed distinct enhanced selectivity to recognize small difference in the molecular shape of polyaromatic hydrocarbons through disordered-to-ordered stale phase transition of the long-chain alkyl moieties, (2)the enhanced selectivity was brought about from multiple carbonyl-π interaction between the stationary phase and solutes, and (3)combination of this HPLC with diastereomerizing agents showed enhanced selectivity for the resultant diastereomers.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] H.Ihara, Y.Goto, T.Sakurai, M.Takafuji, T.Sagawa, S.Nagaoka: "Enhanced Molecular-shape selectivity for polyaromatic hydrocarbons through isotropic-to-crystalline phase transition of poly(octadecyl acrylate)"Chemistry Letters. 2001. 1252-1253 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, T.Sakurai, T.Yamada, T.Hashimoto, M.Takafuji, T.Sagawa, H.Hachisako: "Chirality Control of Self-Assembling Organogels from Lipophilic L-Glutamide Derivative with Metal Chlorides"Langmuir. 18. 7120-7123 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sagawa, S.Fukugawa, T.Yamada, H.Ihara: "Self-Assembled Fibrillar Networks through Highly Oriented Aggregates of Porphyrin, Pyrene, and N, N-Dimethylaniline Hydrophobized by Dialkyl L-Glutamine in Organic Media"Langmuir. 18. 7223-7228 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, T.Sakurai, T.Hashimoto, N.Kido, T.Yamada, T.Sagawa, H.Hachisako, H.Ihara: "Metal ion-induced chirality and morphology control of self-assembling organogels from L-glutamic acid-derived lipids"Chemistry Letters. 2002. 548-549 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, W.Dong, Y.Goto, T.Sakurai, S.Nagaoka, H.Ihara: "Polymer effect on molecular recognition. Enhancement of molecular-shape selectivity for polycyclic aromatic hydrocarbons by poly(acrylonitrile)"Polymer Journal. 34. 437-442 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Goto, K.Nakashima, K.Mitsuishi, M.Takafuji, S.Sakaki, H.Ihara: "Selectivity enhancement for diastereomer separation in RPLC Using crystalline-organic phase-bonded silica instead of simply-hydrophobized silica"Chromatographia. 56. 19-23 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.A.J.Chowdhury, R.I.Boysen, H.Ihara, T.W.Hearn: "Binding behavior of crystalline and noncrystalloine phases : Evaluation of enthalpic and entropic contribution to the seaparation selectivity of nonpolar solutes with a novel chromatographic sorbent"Journal of Pysical Chemistry B. 106. 11936-11950 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sakurai, M.Koga, M.Takafuji, H.Ihara: "Formation of nanofibrillar aggregates by water-soluble beta-structural oligopeptide, (L-Lys-L-Leu)8"Chemistry Letters. 2003. 152-153 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, W.Dong, T.Mimaki, M.Nishihara, T.Sakurai, M.Takafuji, S.Nagaoka: "Poly(4-vinylpyridine) as novel organic phase for RP-HPLC. Unique selectivity for polycyclic aromatic hydrocarbons"Journal of Liquid Chromatography. 26. 2473-2485 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, M.Takafuji, T.Sakurai, M.Katsumoto, N.Ushijima, Tomohiro Shirosaki, H.Hachisako: "Novel self-assembling organogelators by combination of double chain-alkylated L-glutamide and polymeric head group"Organic & Biomolecular Chemistry (J.Chem.Soc., Perkin Trans. I & II). 1. 3004-3006 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, T.Yamada, M.Nishihara, T.Sakurai, M.Takafuji, H.Hachisako, T.Sagawa: "Reversible gelation in organic solution of pyrene substituted by dialkyl L-glutamine : Photophysics of the self-assembled fibrillar network"Journal of Molecular Liquids. 111. 73-76 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, A.Ishiodori, T.Yamada, T.Sakurai, H.Ihara: "Stabilization of enhanced chirality from pyrene-containing L-glutamide lipid in methyl methacrylate by photo-induced polymerization"Chemical Communications. 2004. 1122-1123 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, M.Takafuji, T.Sakurai: "Self-assembled nenofibers in Encyclopedia of Nanoscience & Nanotechnology"American Science Publishers. 23 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, Y.Goto, T.Sakurai, M.Takafuji, T.Sagawa, S.Nagaoka: "Enhanced molecular-shape selectivity for polyaromatic hydrocarbons through isotropic-to-crystalline phase transition of poly(octadecyl acrylate)"Chemistry Letters. 1252-1253 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, T.Sakurai, T.Yamada, T.Hashimoto, M.Takafuji, T.Sagawa, H.Hachisako: "Chirality Control of Self-Assembling Organogels from Lipophilic L-Glutamide Derivative with Metal Chlorides"Langmuir. Vol.18. 7120-7123 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sagawa, S.Fukugawa, T.Yamada, H.Ihara: "Self-Assembled Fibrillar Networks through Highly Oriented Aggregates of Porphyrin, Pyrene, and N,N-Dimethylaniline Hydrophobized by Dialkyl L-Glutamine in Organic Media"Langmuir. Vol.18. 7223-7228 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, T.Sakurai, T.Hashimoto, N.Kido, T.Yamada, T.Sagawa, H.Hachisako, H.Ihara: "Metal ion-induced chirality and morphology control of self-assembling organogels from L-glutamic acid-derived lipids"Chemistry Letters. 548-549 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, W.Dong, Y.Goto, T.Sakurai, S.Nagaoka, H.Ihara: "Polymer effect on molecular recognition. Enhancement of molecular-shape selectivity for polycyclic aromatic hydrocarbons by poly(acrylonitrile)"Polymer Journal. Vol.34. 437-442 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Goto, K.Nakashima, K.Mitsuishi, M.Takafuji, S.Sakaki, H.Ihara: "Selectivity enhancement for diastereomer separation in RPLC Using crystalline-organic phase-bonded silica instead of simply-hydrophobized silica"Chromatographia. Vol.56. 19-23 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.A.J.Chowdhury, R.I.Boysen, H.Ihara, T.W.Hearn: "Binding behavior of crystalline and noncrystalloine phases : Evaluation of enthalpic and entropic contribution to the seaparation selectivity of nonpolar solutes with a novel chromatographic sorbent"Journal of Pysical Chemistry B. Vol.106. 11936-11956 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sakurai, M.Koga, M.Takafuji, H.Ihara: "Formation of nanofibriliar aggregates by water-soluble beta-structural oligopeptide, (L-Lys-L-Leu)8"Chemistry Letters. 152-153 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, W.Dong, T.Mimaki, M.Nishihara, T.Sakurai, M.Takafuji, S.Nagaoka: "Poly(4-vinylpyridine) as novel organic phase for RP-HPLC. Unique selectivity for polycyclic aromatic hydrocarbons"Journal of Liquid Chromatography. Vol.26. 2473-2485 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, M.Takafuji, T.Sakurai, M.Katsumoto, N.Ushijima, Tomohiro Shirosaki, H.Hachisako: "Novel self-assembling organogelators by combination of double chain-alkylated L-glutamide and polymeric head group"Organic & Biomolecular Chemistry(J.Chem.Soc., Perkin Trans.I & II). Vol.1. 3004-3006 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, M.Takafuji, T.Sakurai: "Self-assembled nanofibers"Encyclopedia of Nanoscience & Nanotechnology(American Science Publishers). Vol.9. (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ihara, T.Yamada, M.Nishihara, T.Sakurai, M.Takafuji, H.Hachisako, T.Sagawa: "Reversible gelation in organic solution of pyrene substituted by dialkyl L-glutamine : Photophysics of the self-assembled fibriliar network"Journal of Molecular Liquids. Vol.111. 73-76 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Takafuji, A.Ishiodori, T.Yamada, T.Sakurai, H.Ihara: "Stabilization of enhanced chirality from pyrene-containing L-glutamide lipid in methyl methacrylate by photo-induced polymerization"Chemical Communications. 1122-1123 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 伊藤博隆, 高藤誠, ほか5名: "Reversible gelation in organic solution of pyrene substituted by dialkyl L-glutamine : Photophysics of the self-assembled librillar network"Journal of Molecular Liquids. (印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 伊藤博隆, 高藤誠, ほか5名: "Poly(4-vinylpyridine) as novel organic phase for RP-HPLC. Unique selectivity for polycyclic aromatic hydrocarbons"Journal of Liquid Chromatography. 26. 2473-2485 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Ihara, M.Takafuji, T.Sakurai: "Self-assembled nanofibers"American Science Publishers. (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Takafuji, W.Dong, Y.Goto, T.Sakurai, S.Nagaoka, H.Ihara: "Polymer effect on molecular recognition. Enhancement of molecular-shape selectivity for polycyclic aromatic hydrocarbons by poly (acrylonitrile)"Polymer Journal. 34. 437-442 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Goto, K.Nakashima, K.Mitsuishi, M.Takafuji, S.Sakaki, H.Ihara: "Selectivity enhancement for diastereomer separation in RPLC using crystalline-organic phase-bonded silica instead of simply-hydrophobized silica"Chromatographia. 56. 19-23 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Ihara, W.Dong, T.Mimaki, M.Nishihara, T.Sakurai, M.Takafuji, S.Nagaoka: "Poly(4-vinylpyridine) as novel organic phase for RP-HPLC. Unique selectivity for polycyclic aromatic hydrocarbons"Journal of Liquid Chromatography & Related Technologies. (印刷中).

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Ihara, Y.Goto, T.Sakurai, M.Takafuji, T.Sagawa, S.Nagaoka: "Enhanced Molecular-shape selectivity for polyaromatic hydrocarbons through isotropic-to-crystalline phase transition of poly(octadecyl acrylate)"Chemistry Letters. 1252-1253 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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