2007 Fiscal Year Final Research Report Summary
Ionic Liquid Medaited Activation of Enzymatic Reactions
| Project/Area Number |
17350084
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemistry related to living body
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| Research Institution | Tottori University |
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Principal Investigator |
ITOH Toshiyuki Tottori University, Faculty of Engineering, Professor (50193503)
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| Co-Investigator(Kenkyū-buntansha) |
HAYASE Shuichi Tottori University, Faculty of Enmgineering, Assistant Professor (50238143)
IZUMI Yoshikazu Tottori University, Faculty of Enmgineering, Professor (40026555)
OOSHIRO Takashi Tottori Universily, Faculty of Enmgineering, Lecturer (00233106)
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| Project Period (FY) |
2005 – 2007
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| Keywords | Ionic Liquid / Acceleration / Asymmetric acylation / Organic Solvents / Lipase |
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| Research Abstract |
We discovered that enhanced enantioselectivity was obtained when a novel ionic liquid, i.e. imidazolium polyoxyethylene(10) cetyl sulfate was added at 3 to 10 mol% vs. substrate in the Burkholderia cepacia lipase-catalyzed transesterification of sec-alcohols using vinyl acetate in diisopropyl ether or a hexane solvent system. Further, we found that a remarkable acceleration was also obtained when the lipase was coated with this ionic liquid while still maintaining excellent enantioselectivity. There have been reported only limited examples of means to achieve both acceleration and enhanced enantioselectivity of lipase-catalyzed reaction: PEG coating could accelerate the reaction but caused no significant enhanced enantioselectivity; also, using toluene as solvent caused enhanced enantioselectivity for some substrates but caused no significant activation of the reaction. We used only 28 mg of IL for 1.0 g of lipase in preparing our IL1-coated-lipase PS; the amount was really a trace. We
… More
assume this might be due to the special nature of IL because it consists of imidazolium cation with anionic PEG sulfate and both parts might cooperatively contribute to the activation of the lipase. This is the main concept of our lipase activation method using an ionic liquid.
Ionic liquids are now recognized as solvents for use in lipase-catalyzed reactions, however, there still remains a serious drawback in that the rate of reaction in an ionic liquid is slower than that in a conventional organic solvent. To overcome this problem, attempts have been made to evolve phosphonium ionic liquids appropriate for lipase-catalyzed reaction; several types of phosphonium salts have been prepared and their capability evaluated for use as solvent for the lipase-catalyzed reaction. Very rapid lipase PS-catalyzed transesterification of secondary alcohols was obtained when 2-methoxyethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)imide ([MEB_<u3>P][NTf_2]) was used as solvent, affording the first example of a reaction rate superior to that in diisopropyl ether. Less
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[Journal Article] Regioselective synthesis of trifluoromethyl group substituted allylic amines via palladium catalyzed allylic amination2008
Author(s)
Kawatsura, M., Hirakawa, T., Tanaka, T., Ikeda, D., Hayase, S., Itoh, T
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Journal Title
Tetrahedron Lett 49
Pages: 2450-2453
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Linker-oriented Design of Binaphthol Derivatives for Optical Resolution Using Lipase-catalyzed Reaction2008
Author(s)
Taniguchi, T., Fukuba, T., Nakatsuka, S., Hayade, S., Kawatsura, M., Uno, H, Itoh, T
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Journal Title
J. Org. Chem 73(in press)
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Iron Salt-cataltzed Multi-point Alkylation of Pyrrole with Vinyl Ketones2008
Author(s)
Kawatsura, M., Fujiwara, M., Uehara, H., Nomura, S., Hayase, S., Itoh, T
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Journal Title
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Control of Physical Properties of Ionic Liquids by Point-Difluorination2007
Author(s)
Itoh, T.; Iwai, A.; Tamura, S.; Hayase, S.; Kawatsura, M.
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Journal Title
Abstracts of Papers, 233rd ACS National Meeting, Chicago, United States, March.25-27, ISBN 08412-7438-X
Pages: FLUO-014
Description
「研究成果報告書概要(和文)」より
Peer Reviewed
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[Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification Using an Imizadolium PEG-alkyl Sulfate Ionic Liquid2007
Author(s)
Itoh, T., Matsushita, Y., Abe, Y., Han, S-H., Wada, S., Hayase, S., Kawatsura, M., Takai, S., Morimoto, M., Hirose, Y
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Journal Title
Chem. Lett 36
Pages: 50-51
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Ruthenium-catalysed linear-selective allylic alkylation of allyl acetates2007
Author(s)
Kawatsura, M., Ata, F., Wada, S., Hayase, S., Uno, H., Itoh, T
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Journal Title
Chem. Commun
Pages: 298-300
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] gem-Difluorocyclopropane as Core Molecule Candidate for Liquid Crystal Compounds2007
Author(s)
Itoh, T., Kanbara, M., Ohashi, M., Hayase, S., Kawatsura, M., Kato, T., Miyazawa, K., Takagi, Y., Uno, H
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Journal Title
J. fluorine Chem 128
Pages: 1112-1120
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Synthesis of optically pure cycloalkenols via combination strategy of enzyme-catalyzed reaction and RCM reaction2007
Author(s)
Han, S-H., Hirakawa, T., Fukuba, T., Hayase, S., Kawatsura, M., Itoh, T
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Journal Title
Tetrahedron:Asymmetry 18
Pages: 2484-2490
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Control of Physical Properties of Ionic Liquids by Point-Difluorination2007
Author(s)
Itoh, T., Iwai, A., Tamura, S., Hayase, S., Kawatsura, M
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Journal Title
Abstracts of Papers, 233rd ACS National Meeting, Chicago, United States
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification Using an Imizadolium PEG-alkyl Sulfate Ionic Liquid2006
Author(s)
Itoh, T.; Matsushita, Y.; Abe, Y.; Han, S-H.; Wada, S.; Hayase, S.; Kawatsura, M.; Takai, S.; Morimoto, M.; Hirose, Y.
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Journal Title
Chem. Eur. J. 12
Pages: 9228-9237
Description
「研究成果報告書概要(和文)」より
Peer Reviewed
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[Journal Article] Preparation of Novel Hydrophobic Fluorine-substituted-alkyl sulfate Ionic Liquids and Application as an Efficient Reaction Medium for Lipase-catalyzed Reaction2006
Author(s)
Tsukada, Y.; Iwamoto, K.; Furutani, H.; Matsushita, Y.; Abe, Y.; Matsumoto, K.; Monda, K.; Hayase, S.; Kawatsura, M.; Itoh, T.
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Journal Title
Tetrahedron Lett. 48
Pages: 1801-1804
Description
「研究成果報告書概要(和文)」より
Peer Reviewed
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[Journal Article] Preparation of Novel Hydrophobic Fluorine-substituted-alkyl sulfate Ionic Liquids and Application as an Efficient Reaction Medium for Lipase-catalyzed Reaction2006
Author(s)
Tsukada, Y., Iwamoto, K., Furutani, H., Matsushita, Y., Abe, Y., Matsumoto, K., Monda, K., Hayase, S., Kawatsura, M., Itoh, T
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Journal Title
Tetrahedron Lett 48
Pages: 1801-1804
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] A Novel 1,4-Addition Type Reaction of S -Keto Esters with Vinyl Ketones Catalyzed by Iron(II)tetrafluoroborate in an Ionic Liquid Solvent System2006
Author(s)
Uehara, H., Nomura, S., Hayase, S., Kawatsura, M., Itoh, T
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Journal Title
Electrochemistry 74
Pages: 635-638
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification Using an Imizadolium PEG-alkyl Sulfate Ionic Liquid2006
Author(s)
Itoh, T., Matsushita, Y., Abe, Y., Han, S-H., Wada, S., Hayase, S., Kawatsura, M., Takai, S., Morimoto, M., Hirose, Y
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Journal Title
Chem. Eur. J 12
Pages: 9228-9237
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Activation of Enzyme by the Coating of PEG-alkyl Sulfate Ionic Liquid2007
Author(s)
Itoh, T., Abe, Y., Matsushita, Y., Han, S-H., Hirakawa, T., Hayase, S., Kawatsura, M
Organizer
2nd International Congress on Ionic Liquids(COIL-2)
Place of Presentation
Yokohama, Japan, LMC2 (Invited Lecture)Aug
Year and Date
20070805-10
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Control of Physical Properties of Ionic Liquids Using Fluorine Chemistry2007
Author(s)
Itoh, T., Abe, Y., Kude, K., Iwai, A., Hayase, S., Kawatsura, M
Organizer
Japanese-French Seminar on Fluorine Chemistry, Invited Lecture
Place of Presentation
Reims, France, J8
Year and Date
20070711-13
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Control of Physical Properties of Ionic Liquids by Point-Difluorination2007
Author(s)
Itoh, T., Iwai, A., Tamura, S., Hayase, S., Kawatsura, M
Organizer
233rd ACS National Meeting, USA(ACS Award for Creative Work in Fluorine Chemistry: Symposium in Honor of Kenji Uneyama),(Invited Lecture and Symposium Organizer)
Place of Presentation
Chicago,IL
Year and Date
20070325-27
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Alkylation of Indole, Pyrrole, or Thiophene with Vinyl Ketones Using Iron(II) salts as Catalyst2007
Author(s)
Itoh, T., Ogiso, K., Higuchi, Y., Fujiwara, M., Uehara, H., Nomura, S., Hayase, S., Kawatsura, M
Organizer
2nd International Symposium on Organic Electron Transfer Chemistry(ISOETC-2007)
Place of Presentation
Keio University, Japan, Invited Lecture
Year and Date
20070107-10
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Activation of lipase by the coating of PEG-alkyl sulfate ionic liquid2006
Author(s)
Itoh, T., Abe, Y., Matsushita, Y, Hirakawa, T., Han, S-H., Hayase, S., Kawatsura, M
Organizer
The 9th Japan-Chinae-Korea Joint Symposium on Enzyme Engineering, Ohtsum Siga, 2D1(Oral presentation)
Year and Date
20061030-1102
Description
「研究成果報告書概要(欧文)」より
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[Presentation] NOVEL ALKYLATION OF INDOLE AND PYRROLE DERIVATIVES USINF IRON(ID TETRAFLUOROBORATE IN AN IONIC LIQUID SOLVENT SYSTEM2006
Author(s)
Itoh, T., Uehara, H., Nomura, S., Ogiso, K., Hayase, S., Kawatsura, S
Organizer
ISOCS-22, Saitama, 2006, OC-11 (Oral presentation)
Year and Date
20060822-23
Description
「研究成果報告書概要(欧文)」より
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[Book] Synthesis of novel gem-difluorinatedcyclopropane hybrids: Applications for material and medicinal sciences, "Current Fluoroorganic Chemistry. New Synthetic Directions, Technolo-gies, Materials and Biological Applications", ACS Symposium Series #949, Eds, V.A. So-loshonok, K. Mikami, T. Yamazaki, J. T. Welch, and J. Honek, Chapter 21, pp. 352-362, ISBN 0-8412-7403-72006
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