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 |
Section | 一般 |
Research Field |
Chemistry related to living body
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Research Institution | Tottori University |
Principal Investigator |
ITOH Toshiyuki Tottori University, Faculty of Engineering, Professor (50193503)
|
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)
|
Project Period (FY) |
2005 – 2007
|
Project Status |
Completed (Fiscal Year 2007)
|
Budget Amount *help |
¥15,950,000 (Direct Cost: ¥14,900,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2007: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2006: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥7,900,000 (Direct Cost: ¥7,900,000)
|
Keywords | Ionic Liquid / Acceleration / Asymmetric acylation / Organic Solvents / Lipase / 酵素反応 / 活性化 / 不斉合成 / D-プロリン置換イオン液体 / 酵素コーティング |
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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Report
(4 results)
Research Products
(223 results)
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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
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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
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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 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
Description
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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
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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
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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
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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
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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
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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, 233nd ACS National Meeting, Chicago, United States, March. 25-27, ISBN O8412-7438-X
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[Journal Article] Alkylation of N-protecting group free indole with vinyl ketones using iron salt catalyst2007
Author(s)
Itoh, T., Uehara, H., Ogiso, K., Nomura, S., Hayase, S., Kawatsura, M.
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Journal Title
Chemistry Letters 36・1
Pages: 50-51
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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
Chemical Communications
Pages: 298-300
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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
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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
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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
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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
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[Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification Using an Imizadolium PEG-alkyl Sulfate Ionic Liquid2006
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Chem. Eur. J 12
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[Journal Article] A novel 1,4-addition type reaction of β-keto esters with vinyl ketones catalyzed by iron(II)tetrafluoroborate in an ionic liquid solvent system2006
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Uehara, H., Nomura, S., Hayase, S., Kawatsura, M., Itoh, T.
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Electrochemistry 74・8
Pages: 635-638
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[Journal Article] Enhanced enantioselectivity and remarkable acceleration of lipase-aatalyzed 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 Article] A Novel 1,4-Addition Type Reaction of β-Keto Esters with Vinyl Ketones Catalyzed by Iron(II)tetrafluoroborate in an Ionic Liquid Solvent System2006
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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
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[Presentation] イオン液体によるGeotrichum candidum IFO5767由来酸化還元酵素の活性化,1C7-34,2008
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岡野 渚, 安倍良和, 九手啓佑, 松田知子, 中村 薫, 早瀬修一, 川面 基, 伊藤敏幸
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日本化学会第88春季年会
Place of Presentation
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Year and Date
2008-03-26
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Year and Date
2008-01-14
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[Presentation] Activation of Enzyme by the Coating of PEG-alkyl Sulfate Ionic Liquid, LMC2,招待講演2007
Author(s)
Itoh, T.; Abe, Y.; Matsushita, Y.; Han, S-H.; Hirakawa, T.; Hayase, S.; Ka-watsura, M.
Organizer
2nd International Congress on Ionic Liquids(COIL-2),
Place of Presentation
パシフィコ横浜,横浜
Year and Date
2007-08-06
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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
Description
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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
Description
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[Presentation] Control of Physical Properties of Ionic Liquids by Point-Difluorination2007
Author(s)
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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
Description
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[Presentation] Alkylation of Indole, Pyrrole, or Thiophene with Vinyl Ketones Using Iron(II) salts as Catalyst2007
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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
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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)
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[Presentation] NOVEL ALKYLATION OF INDOLE AND PYRROLE DERIVATIVES USINF IRON(ID TETRAFLUOROBORATE IN AN IONIC LIQUID SOLVENT SYSTEM2006
Author(s)
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Organizer
ISOCS-22, Saitama, 2006, OC-11 (Oral presentation)
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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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