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2008 Fiscal Year Final Research Report

"Organic Synthesis" and "Environmental Cleanup" using Biocatalysts(cyanobacteria etc.)

Research Project

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Project/Area Number 18550142
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Environmental chemistry
Research InstitutionRikkyo University

Principal Investigator

HORIUCHI Akira  Rikkyo University, 理学部, 名誉教授 (60062650)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Kaoru  京都大学, 化学研究所, 准教授 (10101239)
KUNIYOSHI Masayuki  琉球大学, 理学部, 教授 (30045174)
宇月原 貴光  函館工業高等専門学校, 准教授 (90508136)
Project Period (FY) 2006 – 2008
Keywordsものづくり / 環境浄化 / Cyanidioschyzon merolae 10D / Spirulina platensis / Nostoc mintum (NIES-29) / Rhinocladiella atrovirens / 生体触媒
Research Abstract

藍藻(シアノバクテリア)、高温酸性下で生息する原始最古の紅藻類や草津温泉に生息する紅藻類、アルカリ条件下で生息出来て食用としても有用であるスピルリナ等を利用して分解のコントロールを行った。その結果、有意義な有機化合物への変換「ものづくり」と、土壌や水系に存在するポリ塩化ビフェニル(PCB)や芳香族塩素化合物などの環境汚染物質を分解させる「環境浄化」に成果を挙げることが出来た。これらの生体触媒は、有機化合物への変換「ものづくり」に対しては有効な触媒であることが判った。

  • Research Products

    (65 results)

All 2009 2008 2007 2006

All Journal Article (30 results) (of which Peer Reviewed: 27 results) Presentation (21 results) Book (9 results) Patent(Industrial Property Rights) (5 results) (of which Overseas: 2 results)

  • [Journal Article] Recent progress in biocatalysis for asymmetric oxidation and reduction2009

    • Author(s)
      Matsuda, T., Yamanaka, R. and Nakamura, K.
    • Journal Title

      Tetrahedon : Asymmetry (in press)

    • Peer Reviewed
  • [Journal Article] Optical resolution of hexamethylbiphenol by cholesterol esterase and porcine pancreas lipase2008

    • Author(s)
      T. Takemura, G. Emoto, J. Satoh, Y . Kobayashi, T. Utsukihara and C. A. Horiuchi
    • Journal Title

      J. Mol. Catal. B. Enzym. 55

      Pages: 951-954

    • Peer Reviewed
  • [Journal Article] Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens2008

    • Author(s)
      K. Itoh, K. Nakamura, T. Utsukihara, H. Sakamaki and C. A. Horiuchi
    • Journal Title

      Biotechnol Lett 30

      Pages: 951-954

    • Peer Reviewed
  • [Journal Article] Biodegradation of Di-(2-ethylhexyl)phthalateby Fungi2008

    • Author(s)
      W. Chai, M. Suzuki, Y. Handa, M. Murakami, T. Utsukihara, Y. Honma, K. Nakajima, M. Saito and C. A. Horiuchi
    • Journal Title

      Rep. Nat'l. Food Res. Inst 72

      Pages: 83-87

    • Peer Reviewed
  • [Journal Article] Biotransformation of(±)-2-methylcyclohexanone by fungi2008

    • Author(s)
      M. Kawamoto, T. Utsukihara, C. Abe, M. Sato, M. Saito, M. Koshimura, N. Kato, and C. A. Horiuchi
    • Journal Title

      Biotechnol. Lett. 30

      Pages: 1655-1660

    • Peer Reviewed
  • [Journal Article] Biotrans formation of zerumbone by Caragana Chamlagu2008

    • Author(s)
      H. Sakamaki, K. Itoh, S. Kitanaka, S. Sawada and C. A. Horiuchi
    • Journal Title

      Biotechnol. Lett. 30

      Pages: 2025-2029

    • Peer Reviewed
  • [Journal Article] 超臨界二酸化炭素を利用した生体触媒反応の開発2008

    • Author(s)
      松田知子、北爪智哉、原田忠夫、中村薫
    • Journal Title

      超臨界流体技術の開発と応用(佐古猛監修、シーエムシー出版)

      Pages: 178-186

    • Peer Reviewed
  • [Journal Article] Asymmetric reduction of ketones by Geotrichum candidum : immobilization and applica tion to reaction using supercriticalcarbon dioxide2008

    • Author(s)
      Matsuda, T. ; Marukado, R. ; Mukouyama, M. ; Harada, T. ; Nakamura, K.
    • Journal Title

      Tetrahedon : Asymmetry 19

      Pages: 2272-2275

    • Peer Reviewed
  • [Journal Article] Novel Continuous Carboxylation Using Pressurized Carbon Dioxide by Immobilized Decarboxylase2008

    • Author(s)
      Matsuda, T. ; Marukado, R. ; Koguchi, S. ; Nagasawa, T. ; Mukouyama, M. ; Harada, T. ; Nakamura, K.
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 6019-6020

    • Peer Reviewed
  • [Journal Article] Asymmetric Reduction of Ketones with a Germinated Plant2008

    • Author(s)
      Matsuo, K. ; Kawabe, S. ; Tokuda, Y. ; Eguchi, T. ; Yamanaka, R. ; Nakamura, K.
    • Journal Title

      Tetrahedron : Asymm 19

      Pages: 157-159

    • Peer Reviewed
  • [Journal Article] Biotransformation of α-bromo and α, α'-dibromo alkanone by Spirulina platensis2007

    • Author(s)
      T. Utsukihara, S. Okada, and C. A.Horiuchi
    • Journal Title

      J. Mol. Catal. B. Enzym. 45(1-2)

      Pages: 68-72

    • Peer Reviewed
  • [Journal Article] Glyoxal sample preparation for high-performance liquid chromatographic detection of 2, 4-dinitrophenylhydrazone derivative : Suppression of polymerization and mono-derivative formation by using methanol medium2007

    • Author(s)
      K. Nakajima, K. Ohta, T. A. Mostefaoui, W. Chai, T. Utsukihara, C. A. Horiuchi and M. Murakami
    • Journal Title

      J. Chromat. A 1161(1-2)

      Pages: 338-341

    • Peer Reviewed
  • [Journal Article] Reaction of α-halo ketone with 2-aminothiol : a new synthesis of thiazolidines with the oxo group migrated to the original position occupied by halogen atom2007

    • Author(s)
      M. Matsushita, T. T. Takahashi, T.Utsukihara, Y. Shimizu, R. J. Jansen and C. A. Horiuchi
    • Journal Title

      Tetrahedron 63(36)

      Pages: 8932-8938

    • Peer Reviewed
  • [Journal Article] Biotransformation of aromatic heterocyclic compounds by Caragana chamlagu and Wasabia japonica2007

    • Author(s)
      T. Utsukihara, M. Sato, M. Kawamoto, K. Itoh, H. Sakamaki, M. Kuniyoshi and C. A. Horiuchi
    • Journal Title

      J. Mol. Catal. B. Enzym. 48(3-4)

      Pages: 59-63

    • Peer Reviewed
  • [Journal Article] Stereoinversion of 1-arylethanols by Cyanidioschyzon merolae NEIS-13322007

    • Author(s)
      T. Utsukihara, O. Misumi, K. Nakajima, M. Koshimura, M. Kuniyoshi, T. Kuroiwa and C. A. Horiuchi
    • Journal Title

      J. Mol. Catal. B. Enzym. 51(1-2)

      Pages: 19-23

    • Peer Reviewed
  • [Journal Article] Reaction of α, β-unsaturated ketones using cerium(IV)sulfate tetrahydrate in acetic acid2007

    • Author(s)
      K. Itoh, T. Utsukihara, K. Funayama, H. Sakamaki, M. Kanamori, T. T. Takahashi, Y. Saitoh, M. Matsushita, L. He, C. Hashimoto, T. Sugiyama and C. A. Horiuchi
    • Journal Title

      Appl. Organometal. Chem. 21

      Pages: 1029-1032

    • Peer Reviewed
  • [Journal Article] 発光ダイオードを利用した植物の機能強化2007

    • Author(s)
      河邊誠一郎、松尾清子、徳田陽祐、中村薫
    • Journal Title

      倉敷芸術科学大学紀要 12

      Pages: 69-76

  • [Journal Article] 超臨界二酸化炭素を利用した生体触媒反応の開発2007

    • Author(s)
      松田知子、北爪智哉、原田忠夫、中村薫
    • Journal Title

      バイオインダストリー 24

      Pages: 24-31

    • Peer Reviewed
  • [Journal Article] Control of chemoselectivity of microbial reaction with resin adsorbent : enhancement of Baeyer-Villiger oxidation over reduction2007

    • Author(s)
      Fujii, M. ; Akita, H. ; Ida, Y. Nakagawa, T. Nakamura, K.
    • Journal Title

      Appl. Microb. Biotech 77

      Pages: 45-51

    • Peer Reviewed
  • [Journal Article] Butadiene Polymerization Catalyzed by Lanthanide Metallocene-Alkyl aluminum Complexes with Cocatalysts : Metal-Dependent Control of 1, 4-Cis/Trans Stereoselectivity and Molecular Weight2006

    • Author(s)
      S. Kaita, M. Yamanaka, C. A. Horiuchi, and Y. Wakatsuki
    • Journal Title

      Macromolecules 39

      Pages: 1359-1363

    • Peer Reviewed
  • [Journal Article] Reduction of various ketones by red algae2006

    • Author(s)
      T. Utsukihara, O. Misumi, N. Kato, T. Kuroiwa and C. Akira Horiuchi
    • Journal Title

      Tetrahedron Asymmetry 17

      Pages: 1179-1185

    • Peer Reviewed
  • [Journal Article] Stereoselective reduction of ketones by various vegetables2006

    • Author(s)
      T. Utsukihara, S. Watanabe, A. Tomiyama, W. Chai and C. A. Horiuchi
    • Journal Title

      J. Mol. Catal. B. Enzym 41

      Pages: 103-109

    • Peer Reviewed
  • [Journal Article] Reaction of α, β-unsaturated ketone with cerium(IV)salts in alcohol2006

    • Author(s)
      C. A. Horiuchi, Y. Saitoh, T. Utsukihara, S. Takahashi, M. Matsushita, L. He, T. T. Takahashi, C. Hashimoto, T. Sugiyama and S. Nozaki
    • Journal Title

      Applied Organomet. Chem. 20(10)

      Pages: 663-668

    • Peer Reviewed
  • [Journal Article] Reaction of5α-Cholest-2-ene with Iodine-Copper(II)Acetate2006

    • Author(s)
      T. Utsukihara, Y. Yokoyama, K. Kaneko, I. Yoshino, T. Miyasaka, J. Y. Satoh, M. Kuniyoshi, and C. A. Horiuchi
    • Journal Title

      Bulletin of the Faculty of Science, University of the Ryukyus 81

      Pages: 77-87

  • [Journal Article] Microwave-assisted synthesis of<-hydroxy-and<-diketone and pyrazine derivative from α-halo and α, α'-dibromo ketone2006

    • Author(s)
      T. Utsukihara, H. Nakamura, M. Watanabe and C. A. Horiuchi
    • Journal Title

      Tetrahedron Lett. 47(52)

      Pages: 9359-9364

    • Peer Reviewed
  • [Journal Article] 有機金属錯体、金属塩を利用する合成反応から生体触媒に至るまで2006

    • Author(s)
      堀内昭
    • Journal Title

      バイオインダストリー 23(4)

      Pages: 37-47

    • Peer Reviewed
  • [Journal Article] Chemoenzymatic synthesis of optically active c-alkyl-c-butenolides2006

    • Author(s)
      Fujii, M. ; Fukumura, M. ; Hori, Y. ; Hirai, Y. ; Akita, H. ; Nakamura, K. ; Toriizuka, K. ; Ida, Y.
    • Journal Title

      Tetrahedron : Asymm. 17

      Pages: 2292-2298

    • Peer Reviewed
  • [Journal Article] 成長光条件の異なるブロッコリースプラウトが腸管上皮細胞からのIL-7・TGF-分泌に及ぼす影響2006

    • Author(s)
      真部真里子、中村薫
    • Journal Title

      日本食品工業会誌 53

      Pages: 437-442

    • Peer Reviewed
  • [Journal Article] Biocatalytic Reduction of Carbonyl Group2006

    • Author(s)
      Nakamura, K. ; Matsuda, T.
    • Journal Title

      Current Organic Chemistry 10(11)

      Pages: 1217-1246

    • Peer Reviewed
  • [Journal Article] 芽生え植物を用いた有用物質の変換2006

    • Author(s)
      松尾清子、河邊誠一郎、徳田洋祐、江口剛史、山中理央、中村薫
    • Journal Title

      倉敷芸術科学大学紀要 11

      Pages: 71-78

  • [Presentation] タバコ培養細胞を用いたケトン類の不斉還元2008

    • Author(s)
      岡田亜希子・小島秀夫・竹田恵美・中村薫
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大
    • Year and Date
      2008-12-04
  • [Presentation] 含フッ素芳香族化合物の不斉還元・速度論的光学分割に関する検討2008

    • Author(s)
      阿部智香・岩永裕作・東利則・中村薫・須貝威
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大
    • Year and Date
      2008-12-04
  • [Presentation] 生体触媒反応における竹粉の利用2008

    • Author(s)
      西山真一・上地眞一・中村薫
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大
    • Year and Date
      2008-12-04
  • [Presentation] 微細藻類によるケトンの不斉還元2008

    • Author(s)
      濱真央樹・堀常純哉・上地眞一・中村薫
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大
    • Year and Date
      2008-12-04
  • [Presentation] 生体触媒研究の未来2008

    • Author(s)
      中村薫
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大(招待講演)
    • Year and Date
      2008-12-04
  • [Presentation] Nostoc minutumによる2-ハロアセトフェノン誘導体の変換反応2008

    • Author(s)
      越村匡博・宇月原貴光・木山明日香・国吉正之・堀内昭
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      東邦大
    • Year and Date
      2008-12-04
  • [Presentation] マイクロ波の照射によるキノキサリン誘導体の合成2008

    • Author(s)
      宇月原貴光・橘田和憲・横関慈生・遠藤可奈子・竹村哲雄・堀内昭
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      県民文化センター福山
    • Year and Date
      2008-11-22
  • [Presentation] 硝酸銅(II)を用いた3-アシルイソオキサゾール誘導体の合成2008

    • Author(s)
      佐藤浩章・伊藤賢一・青山忠・堀内昭・滝戸俊夫
    • Place of Presentation
      県民文化センター福山
    • Year and Date
      2008-11-22
  • [Presentation] Biotransformation of bromosesquiterpenes by fungus2008

    • Author(s)
      Masahiro Koshimura, Takamitsu Utsukihara, Mai Kawamoto, Michihiko Saito, Masayuki Kuniyoshi and C. A. Horiuchi
    • Organizer
      17the International Conference on Organic Synthesis
    • Place of Presentation
      Korea, Daejeon
    • Year and Date
      2008-06-24
  • [Presentation] 有機金属錯体、金属塩を利用する合成反応から生体触媒への道2008

    • Author(s)
      堀内昭・宇月原貴光
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大(招待講演)
    • Year and Date
      2008-03-29
  • [Presentation] ダークパール・バジルおよびスイート・バジル培養細胞による1-フェニルエタノール類の立体選択的反応2008

    • Author(s)
      伊藤賢一・中村薫・酒巻弘・宇月原貴光・堀内昭
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大
    • Year and Date
      2008-03-28
  • [Presentation] ステロイド、π-アリルパラジウム錯体、ヨウ素を利用する合成反応から生体触媒に至るまで2007

    • Author(s)
      堀内昭
    • Place of Presentation
      豊田工大(特別講演)
    • Year and Date
      2007-07-30
  • [Presentation] マイクロ波照射によるキノキサリン誘導体の効率的合成2007

    • Author(s)
      橘田和憲・宇月原貴光・須貝威・堀内昭
    • Organizer
      新規素材探索研究会
    • Place of Presentation
      新横浜フジビューH
    • Year and Date
      2007-06-02
  • [Presentation] スピルリナ(Spirulina subsalsa)によるヒドロキシ誘導体の酸化2006

    • Author(s)
      岡田伸之介、木山明日香、宇月原貴光、加藤中英、堀内昭
    • Organizer
      第10回生体触媒シンポジウム
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2006-12-14
  • [Presentation] Nostoc mintumによるアセトフェノン誘導体の還元2006

    • Author(s)
      阿部智香、宇月原貴光、堀内昭
    • Organizer
      第10回生体触媒シンポジウム
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2006-12-14
  • [Presentation] ムレスズメ培養細胞によるインドール誘導体等の酸化開裂反応(2)2006

    • Author(s)
      佐藤迪子、酒巻弘、伊藤賢一、宇月原貴光、柴文、堀内昭
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      琉球大
    • Year and Date
      2006-11-18
  • [Presentation] シアニディオシゾンを利用するフェニルエタノールの光学異性化2006

    • Author(s)
      宇月原貴光、橋元親夫、高橋知義、三角修己、黒岩常祥、加藤中英、堀内昭
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      琉球大
    • Year and Date
      2006-11-18
  • [Presentation] カビによるシクロアルカノンのBaeyer-Villiger型酸化2006

    • Author(s)
      川元真依、宇月原貴光、横山裕矢、阿部智香、国吉正之、斉藤道彦、加藤中英、堀内昭
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      琉球大
    • Year and Date
      2006-11-18
  • [Presentation] Synthesis ofpyrazine derivatives from 2-bromoketone using microwave2006

    • Author(s)
      T. Utsukihara, M. Watanabe, T. T. Takahashi and C. A. Horiuchi
    • Organizer
      1st International IUPAC Conference on Green-Sustainable Chemistry
    • Place of Presentation
      Germany Dresden Tecnol. Univ.
    • Year and Date
      2006-09-12
  • [Presentation] Baeyer-Villiger oxidation of cycloalkanone derivatives by fungi2006

    • Author(s)
      M. Kawamoto, T. Utsukihara, M. Saito, N. Kato and C. A. Horiuchi
    • Organizer
      1st International IUPAC Conference on Green-Sustainable Chemistry
    • Place of Presentation
      Germany Dresden Tecnol. Univ.
    • Year and Date
      2006-09-12
  • [Presentation] Biotransformation of alcohols by Spirulina subsals NIES-392006

    • Author(s)
      S. Okada, A. Matsuda, T. Utsukihara, W. Chai, T. T. Takahashi, N. Kato and C. A. Horiuchi
    • Organizer
      1st International IUPAC Conference on Green-Sustainable Chemistry
    • Place of Presentation
      Germany Dresden Tecnol. Univ.
    • Year and Date
      2006-09-12
  • [Book] Practical Methods in Biocatalysis and Biotransformations2009

    • Author(s)
      Takamitsu Utsukihara and C.Akira Horiuchi
    • Publisher
      VCH-Wiley(Volume 5(catalysts for regio-or stereo-selective oxidations/reductions)(In press)
  • [Book] Enzymatic Reduction Reaction in" Asymmetric Organic Synthesis with Enzymes"2009

    • Author(s)
      Kaoru Nakamura and Tomoko Matsuda
    • Total Pages
      193-228
    • Publisher
      Wiley-VCH Verlag GmbH & Co.
  • [Book] Biotransformation of Some Compounds using Potato2008

    • Author(s)
      Takamitsu Utsukihara and C.Akira Horiuchi
    • Total Pages
      131-144
    • Publisher
      Global Science Books
  • [Book] Enzyme-catalyzed Reduction of Carbonyl Compounds in "Modern Reduction Methods"2008

    • Author(s)
      Kaoru Nakamura and Tomoko Matsuda
    • Total Pages
      209-234
    • Publisher
      VCH-Wiley
  • [Book] Biocatalytic Reduction of Carbonyl Groups in "Selective Biocatalysis : Fronteers in Organic Chemistry"2007

    • Author(s)
      Kaoru Nakamura and Tomoko Matsuda
    • Publisher
      Bentham Science Publisher Ltd
  • [Book] "Future directions in photosynthe ic organisms-catalyzed reactions" in "Future Dire tions in Biocatalysis"2007

    • Author(s)
      Nakamura, K.
    • Total Pages
      51-58
    • Publisher
      Ed. Matsuda T. Elsevier
  • [Book] Synthesis of both enantiomers of 1-phenylethanol by Reduction of acetohpnenone with Geotrichum candidum IFO 5767" in "Catalysts for Fine Chemical Synthesis Volume 5 : Regio-and Stereo-Controlled Oxidations and Reductions"2007

    • Author(s)
      Nakamura, K. ; Fujii, M. ; Ida Y.
    • Total Pages
      93-97
    • Publisher
      Eds. Roberts, S. M. ; Whittall, John, John Wiley & Sons
  • [Book] "Biocatalysis in water" in "Organic Reactions in Water-Principles, Strategies and Methods." Ulf Lindstr ed.2007

    • Author(s)
      Kamura, K. ; Matsuda, T.
    • Total Pages
      301-349
    • Publisher
      Blackwell Publishing
  • [Book] "Synthesis of Chiral Fluorinated Materials via Biotransformation" in "Advances in Organic Synthesis-Modern Organofluorine Chemistry-Synthetic Aspects"2006

    • Author(s)
      Kitazume, T. ; Matsuda T. ; Nakamura, K.
    • Total Pages
      463-490
    • Publisher
      Vol 2. Laali, K. K. ed. Bentham Science Publishers, Hilversum
  • [Patent(Industrial Property Rights)] Method for manufacturing isoxazole derivative or dihydroisoxazole derivative2008

    • Inventor(s)
      C. Akira Horiuchi, Ken-ichi Itoh, Noriko Nakazato,Hideo Iwai, Takamitsu Utsukihara and Wen Chai
    • Industrial Property Rights Holder
      立教学院
    • Industrial Property Number
      US2006/0247288A1
    • Filing Date
      2008-12-26
    • Overseas
  • [Patent(Industrial Property Rights)] 2-ヒドロキシケトンまたは1,2-ジケトンの製造方法2006

    • Inventor(s)
      堀内昭・中村浩章・宇月原貴光・柴文
    • Industrial Property Rights Holder
      立教学院
    • Patent Publication Number
      特開2006-30685
    • Filing Date
      2006-11-09
  • [Patent(Industrial Property Rights)] イソオキサゾール誘導体又はジヒドロイソオキサゾール誘導体の製造方法2006

    • Inventor(s)
      堀内昭・伊藤賢一・中里紀子・岩井英郎・宇月原貴光・柴文
    • Industrial Property Rights Holder
      立教学院
    • Industrial Property Number
      特許第3789465号
    • Filing Date
      2006-04-07
  • [Patent(Industrial Property Rights)] 1,2,4-オキサジアゾール誘導体の製造方法2006

    • Inventor(s)
      堀内昭・伊藤賢一・酒巻弘
    • Industrial Property Rights Holder
      立教学院
    • Industrial Property Number
      特許第3776112号
    • Filing Date
      2006-03-03
  • [Patent(Industrial Property Rights)] ヒトパピローマウイルス症患治治療薬および抗ヒト免疫不全ウイルス薬2006

    • Inventor(s)
      坂上宏・川添豊・大槻マミ太郎・稲葉葉一・柴文・堀内昭・中島秀喜・荒津千明
    • Industrial Property Rights Holder
      (株)日本生薬研究所
    • Industrial Property Number
      国際WO 2006/001364
    • Filing Date
      2006-01-05
    • Overseas

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Published: 2010-06-10   Modified: 2016-04-21  

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