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2010 Fiscal Year Final Research Report

Chirality Control of "Asymmetric Oxygen Atom" generated by Metal Ion Coordination

Research Project

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Project/Area Number 20550065
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Inorganic chemistry
Research InstitutionNara Women's University

Principal Investigator

MIKATA Yuji  Nara Women's University, 共生科学研究センター, 准教授 (10252826)

Project Period (FY) 2008 – 2010
Keywords金属錯体化学
Research Abstract

In this project, by careful design of the ligand and the selection of metal ion, we are going to clarify the possibility of the chirality generated on the metal-coordinated oxygen atom and its limitation, proposing the brand-new concept of "Asymmetric Oxygen". By appropriate design of the ligand, we are going to isolate and characterize the enantiomer based on exclusively "Asymmetric Oxygen". At the same time, we are going to analyze the physical properties of the compound in order to find possible application of "Asymmetric Oxygen".
At first, we examined the possible factors that are necessary to coordinate the achiral oxygen atom to the metal center. On the basis of this study, we constructed the system in which asymmetric oxygen and asymmetric nitrogen are generated simultaneously in the complex, and found that the configuration of the asymmetric nitrogen controls the configuration of the asymmetric oxygen. Furthermore, we succeeded in generating asymmetric oxygen atom using a ligand with an asymmetric carbon atom in various positions. X-ray crystallography of copper complexes revealed that the configuration of asymmetric oxygen controls the configuration of asymmetric oxygen atom. The chiral complexes exhibited characteristic Cotton effect in the d-d transition region of copper atom. This indicates that the configuration of asymmetric oxygen is preserved in solution state.

  • Research Products

    (43 results)

All 2011 2010 2009 2008

All Journal Article (21 results) (of which Peer Reviewed: 21 results) Presentation (22 results)

  • [Journal Article] Crystal structures and chiral recognition of the diastereomeric salts prepared from 2-methoxy-2-(1-naphthyl)propanoic acid2011

    • Author(s)
      A.Ichikawa, H.Ono, T.Echigo, Y.Mikata
    • Journal Title

      CrystEngComm in press

    • Peer Reviewed
  • [Journal Article] Methoxyquinolinediethylenetriamine conjugate as a fluorescent zinc sensor2011

    • Author(s)
      Y.Mikata, A.Yamashita, K.Kawata, H.Konno, S.Itami, K.Yasuda, S.Tamotsu
    • Journal Title

      Dalton Transactions in press

    • Peer Reviewed
  • [Journal Article] Intramolecular Ether Oxygen Coordination in the Zinc Complexes with Dipicolylamine (DPA)-Derived Ligands2011

    • Author(s)
      Y.Mikata, T.Fujimoto, T.Fujiwara, S.Kondo
    • Journal Title

      Inorg.Chim.Acta in press

    • Peer Reviewed
  • [Journal Article] Methoxy-substituted isoTQEN family for enhanced fluorescence response toward zinc ion2011

    • Author(s)
      Y.Mikata, A.Yamashita, K.Kawata, H.Konno, S.Itami, K.Yasuda, S.Tamotsu
    • Journal Title

      Dalton Transactions 40(16)

      Pages: 4055-4066

    • Peer Reviewed
  • [Journal Article] Bismuth heterocycles based on a diphenyl sulfone scaffold : Synthesis and substituent effect on the antifungal activity against Saccharomyces cerevisiae2011

    • Author(s)
      T.Murafuji, Y.Fujiwara, D.Yoshimatsu, I.Miyakawa, K.Migita, Y.Mikata
    • Journal Title

      Eur.J.Med.Chem. 46

      Pages: 519-525

    • Peer Reviewed
  • [Journal Article] Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes : Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction2010

    • Author(s)
      S.Yamazaki, Y.Yamamoto, Y.Fukushima, M.Takebayashi, T.Ukai, Y.Mikata
    • Journal Title

      J.Org.Chem. 75(15)

      Pages: 5216-5222

    • Peer Reviewed
  • [Journal Article] Cationic technetium and rhenium complexes with pendant carbohydrates2010

    • Author(s)
      C.L.Ferreira, F.L.N.Marques, M.R.Y.Okamoto, A.H.Otake, Y.Sugai, Y.Mikata, T.Storr, M.Bowen, S.Yano, M.J.Adam, R.Chammas, C.Orvig
    • Journal Title

      Appl.Radiat.Isotopes 68(6)

      Pages: 1087-1093

    • Peer Reviewed
  • [Journal Article] Crystal conformations and molecular packing of (S)-2-methoxy-2-(9-phenanthryl)propanoic acid and a diastereomeric amide prepared from (R)-2-methoxy-2-(1-naphthyl)propanoic acid2010

    • Author(s)
      A.Ichikawa, H.Ono, M.Takenaka, Y.Mikata
    • Journal Title

      CrystEngComm. 12(7)

      Pages: 2261-2268

    • Peer Reviewed
  • [Journal Article] Control of aggregation property of tris(maltohexaose)-linked porphyrins with an alkyl chain2010

    • Author(s)
      Y.Mikata, T.Sawaguchi, T.Kakuchi, M.Gottschaldt, U.S.Schubert, H.Ohi, S.Yano
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 663-671

    • Peer Reviewed
  • [Journal Article] Antioxidant action of sugar-pendant C60 fullerenes2009

    • Author(s)
      M.Horie, A.Fukuhara, Y.Saito, Y.Yoshida, H.Sato, H.Ohi, M.Obata, Y.Mikata, S.Yano, E.Niki
    • Journal Title

      Bioorg.Med.Chem.Lett. 19(20)

      Pages: 5902-5904

    • Peer Reviewed
  • [Journal Article] Copper(II) and zinc(II) complexes with C-glycoside-pendant dipicolylamine (DPA)-amino acid conjugates2009

    • Author(s)
      Y.Mikata, S.Fujii, M.Naemura, K.Takahashi, Y.Noguchi
    • Journal Title

      Dalton Trans. (46)

      Pages: 10305-10310

    • Peer Reviewed
  • [Journal Article] Zinc-Catalyzed Reactions of Ethenetricarboxylates with 2-(Trimethylsilylethynyl) anilines Leading to Bridged Quinoline Derivatives2009

    • Author(s)
      S.Yamazaki, S.Morikawa, K.Miyazaki, M.Takebayashi, Y.Yamamoto, T.Morimoto, K.Kakiuchi, Y.Mikata
    • Journal Title

      Org.Lett. 11(13)

      Pages: 2796-2799

    • Peer Reviewed
  • [Journal Article] Bisquinoline-based fluorescent zinc sensors2009

    • Author(s)
      Y.Mikata, A.Yamashita, A.Kawamura, H.Konno, Y.Miyamoto, S.Tamotsu
    • Journal Title

      Dalton Trans. (19)

      Pages: 3800-3806

    • Peer Reviewed
  • [Journal Article] Lewis acid-promoted reactions of ethenetricarboxylates with γ-CF_3-substituted propargyl alcohols2009

    • Author(s)
      S.Yamazaki, Y.Yamamoto, Y.Mikata
    • Journal Title

      Tetrahedron 65(10)

      Pages: 1988-1994

    • Peer Reviewed
  • [Journal Article] Preparation and conformational analysis of C-glycosyl β-and β/β-peptides2009

    • Author(s)
      Y.Inaba, T.Kawakami, S.Aimoto, T.Ikegami, T.Takeuchi, T.Nakazawa, S.Yano, Y.Mikata
    • Journal Title

      Carbohydr.Res. 344(5)

      Pages: 613-626

    • Peer Reviewed
  • [Journal Article] Feasible attachment of dinuclear ruthenium complex to gold electrode surface via new ligand substitution reaction2009

    • Author(s)
      H.Takagi, Y.Mikata, A.Ichimura, T.Yano, I.Kinoshita, M.Hori, T.J.Collins, M.Gottschaldt, S.Yano
    • Journal Title

      Electochimica Acta 54(4)

      Pages: 1286-1291

    • Peer Reviewed
  • [Journal Article] Characteristic conformations and molecular packings in crystal structures of diastereomeric esters prepared from (S)-2-methoxy-2-(1-naphthyl)propanoic acid2008

    • Author(s)
      A.Ichikawa, H.Ono, Y.Mikata
    • Journal Title

      Tetrahedron : Asymmetry 19(23)

      Pages: 2693-2698

    • Peer Reviewed
  • [Journal Article] The Isoquinoline-Based TQEN Family as TPEN-Derived Fluorescent Zinc Sensors2008

    • Author(s)
      Y.Mikata, A.Yamanaka, A.Yamashita, S.Yano
    • Journal Title

      Inorg.Chem. 47(16)

      Pages: 7295-7301

    • Peer Reviewed
  • [Journal Article] Syntheses, structural characterization and photophysical properties of 4-(2-pyridyl)-1, 2, 3-triazole rhenium(I) complexes2008

    • Author(s)
      M.Obata, A.Kitamura, A.Mori, C.Kameyama, J.Czaplewska, R.Tanaka, I.Kinoshita, T.Kusumoto, H.Hashimoto, M.Harada, Y.Mikata, T.Funabiki, S.Yano
    • Journal Title

      Dalton Trans. (25)

      Pages: 3292-3300

    • Peer Reviewed
  • [Journal Article] A general route to pendant C-glycosyl 1, 2-and 1, 3-diamines2008

    • Author(s)
      Y.Inaba, T.Fujimoto, H.Ono, M.Obata, S.Yano, Y.Mikata
    • Journal Title

      Carbohydr.Res. 343(5)

      Pages: 941-950

    • Peer Reviewed
  • [Journal Article] Preparation of C-glycoside pendant β2-and β2, 2-amino acids2008

    • Author(s)
      Y.Inaba, S.Yano, Y.Mikata
    • Journal Title

      Bull.Chem.Soc.Jpn. 81(5)

      Pages: 606-616

    • Peer Reviewed
  • [Presentation] キノリン部位を有する糖含有エチレンジアミン誘導体の亜鉛イオン選択的蛍光応答2011

    • Author(s)
      鵜飼杏奈・三方裕司
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      東京
    • Year and Date
      2011-03-28
  • [Presentation] 複素環芳香族置換グリシン誘導体を配位子とする金属錯体の合成と構造2011

    • Author(s)
      河田景子・三方裕司
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      東京
    • Year and Date
      2011-03-26
  • [Presentation] Mercury(II)-selective fluorescent response of bisquinoline derivatives with thioether linkage.2010

    • Author(s)
      三方裕司, 中垣芙美恵
    • Organizer
      Pacifichem 2010 Congress
    • Place of Presentation
      Waikiki, USA
    • Year and Date
      2010-12-19
  • [Presentation] Fluorescent response of isoquinoline-based amine derivatives toward zinc ion.2010

    • Author(s)
      河田景子, 三方裕司
    • Organizer
      Pacifichem 2010 Congress
    • Place of Presentation
      Waikiki, USA
    • Year and Date
      2010-12-19
  • [Presentation] Carbohydrate-appended metal complexes for enhanced cellular uptake of metal ion.2010

    • Author(s)
      三方裕司, 野口友華, 高橋京子
    • Organizer
      Pacifichem 2010 Congress
    • Place of Presentation
      Waikiki, USA
    • Year and Date
      2010-12-16
  • [Presentation] Quinoline-and isoquinoline-based molecular design for functional metal complexes.2010

    • Author(s)
      三方裕司
    • Organizer
      17th International SPACC-CSJ Symposium
    • Place of Presentation
      Kagoshima INVITED LECTURE
    • Year and Date
      2010-10-15
  • [Presentation] 亜鉛イオン特異的蛍光応答を示すトリス(1-イソキノリルメチル)アミン誘導体の開発2010

    • Author(s)
      河田景子・三方裕司
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2010-09-29
  • [Presentation] 金属の細胞内導入を目指した糖含有配位子の開発2010

    • Author(s)
      高橋京子・三方裕司
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2010-09-28
  • [Presentation] 糖含有配位子を用いた細胞への金属イオン導入2010

    • Author(s)
      高橋京子・三方裕司
    • Organizer
      第4回バイオ合同シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2010-09-25
  • [Presentation] エーテル酸素原子が金属中心に配位した亜鉛錯体の合成と構造2010

    • Author(s)
      藤原知美・三方裕司
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-28
  • [Presentation] イソキノリン部位を有するアミン誘導体の亜鉛イオン選択的蛍光応答2010

    • Author(s)
      河田景子・三方裕司
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-27
  • [Presentation] キノリン骨格を有するアルカンチオエーテル配位子の水銀(II)イオン選択的蛍光応答2010

    • Author(s)
      中垣芙美恵・三方裕司
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-27
  • [Presentation] 生物学的応用を目的とした糖含有配位子の開発2010

    • Author(s)
      野口友華・三方裕司
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-26
  • [Presentation] キノリン骨格を有するチオエーテル配位子の水銀イオンに対する蛍光応答2009

    • Author(s)
      中垣芙美恵・三方裕司
    • Organizer
      第59回錯体化学討論会
    • Place of Presentation
      長崎
    • Year and Date
      2009-09-26
  • [Presentation] 新規糖含有アニオン性配位子を用いた金属錯体の開発2009

    • Author(s)
      野口友華・三方裕司
    • Organizer
      第59回錯体化学討論会
    • Place of Presentation
      長崎
    • Year and Date
      2009-09-25
  • [Presentation] The Isoquinoline-Based TQEN Family as TPEN-Derived Fluorescent Zinc Sensors.2009

    • Author(s)
      三方裕司
    • Organizer
      ICBIC
    • Place of Presentation
      Nagoya
    • Year and Date
      2009-07-27
  • [Presentation] The TQEN (Tetrakis(2-quinolylmethylethylenedia mine)) Family as Fluorescent Zinc Sensors.2009

    • Author(s)
      三方裕司
    • Organizer
      PPC 2009
    • Place of Presentation
      Shiga INVITED LECTURE
    • Year and Date
      2009-07-10
  • [Presentation] Development of Isoquinoline-Based Fluorescent Zinc Sensor with High Affinity.2008

    • Author(s)
      山下梓, 三方裕司
    • Organizer
      14th International SPACC-CSJ Symposium
    • Place of Presentation
      Osaka
    • Year and Date
      2008-11-20
  • [Presentation] Development of Carbohydrate-Based Ligand Bearing N-(2-Pyridylmethyl)glycine Frame.2008

    • Author(s)
      野口友華, 三方裕司
    • Organizer
      14th International SPACC-CSJ Symposium
    • Place of Presentation
      Osaka
    • Year and Date
      2008-11-20
  • [Presentation] Design for Hg-selective fluorescent probes with alkanedithiol scaffold.2008

    • Author(s)
      中垣芙美恵, 三方裕司
    • Organizer
      14th International SPACC-CSJ Symposium
    • Place of Presentation
      Osaka
    • Year and Date
      2008-11-20
  • [Presentation] メトキシイソキノリン部位を有するエチレンジアミン誘導体の亜鉛イオンに対する蛍光応答2008

    • Author(s)
      山下梓・三方裕司
    • Organizer
      第58回錯体化学討論会
    • Place of Presentation
      金沢
    • Year and Date
      2008-09-20
  • [Presentation] 高い親和性を有する蛍光性亜鉛イオンキレーターの開発2008

    • Author(s)
      三方裕司・山中あずさ・山下梓
    • Organizer
      第3回バイオ関連化学合同シンポジウム
    • Place of Presentation
      横浜
    • Year and Date
      2008-09-19

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Published: 2012-01-26   Modified: 2016-04-21  

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