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Stabilization of "Asymmetric Oxygen" derived from Metal-Coordinated Oxygen Atom

Research Project

Project/Area Number 18550059
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, KYOUSEI Science Center for Life and Nature, Associate Professor (10252826)

Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥4,240,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥540,000)
Fiscal Year 2007: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2006: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsAsymmetric Oxygen Atom / Metal Coordination / Metal Complex / Ether Oxygen / Chirality / Asymmetric Coordination / O-Glycoside / S-Glycoside
Research Abstract

It is well known that a nitrogen lone pair inverts via pyramidal inversion, causing expeditious loss of chirality at a stereogenic nitrogen center. But metal-coordinated nitrogen atoms have been demonstrated as an asymmetric nitrogen. Similarly, it is possible that the oxygen atom of a unsymmetrical ether can become a chiral center when coordinated to a metal ion. In this case also, the chirality is extremely unstable due to the rapid inversion of the remaining oxygen lone pair. Preventing lone pair inversion by metal ion coordination is a potential route to compounds exhibiting a chiral oxygen atom. Strong coordination of the metal ion to the ether oxygen atom may lead to the necessary differentiation of the two oxygen lone pairs. Careful ligand design is needed in any effort to isolate a compound with a metal-bound asymmetric oxygen atom. In this project, controlling factors for the assembly of asymmetric oxygen atoms are discussed, including the effect of ligand structure, counterion, and solvent in a series of dipicolylamine-copper (II) complexes

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (44 results)

All 2008 2007 2006

All Journal Article (24 results) (of which Peer Reviewed: 13 results) Presentation (20 results)

  • [Journal Article] Preparation of C-glycoside pendant β^2-and β^<2,2>-amino acids2008

    • Author(s)
      Y. Inaba
    • Journal Title

      Bull. Chem. Soc. Jpn. 81(印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] A general route to pendant C-glycosyl 1,2-and 1,3-diamines2008

    • Author(s)
      Y. Inaba
    • Journal Title

      Carbohydr. Res. 343(5)

      Pages: 941-950

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • 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
    • Journal Title

      Dalton Trans (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Preparation of C-glycoside pendant β^2- and β^<2.2>-amino acids2008

    • Author(s)
      Y. Inaba
    • Journal Title

      Bull. Chem. Soc. Jpn (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] A general route to pendant C-glycosyl 1,2- and 1,3-diamines2008

    • Author(s)
      Y. Inaba
    • Journal Title

      Carbohydr. Res 343(5)

      Pages: 941-950

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Syntheses, structural characterization and photophysical properties of 4-(2-pyridyl)-1,2,3-triazole rhenium(I) complexes2008

    • Author(s)
      M. Obata
    • Journal Title

      Dalton Trans (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Characterization of azulenylphosphine derivatives. Unexpected debromination and its synthetic utility in the preparation of 2-substituted azulene2007

    • Author(s)
      A. F. M. M. Rahman
    • Journal Title

      Organometallics 26(12)

      Pages: 2971-2977

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Control of Intramolecular Oxygen Coordination in the Crystal Structure of the Copper (II) Complexes with Dipicolylamine (DPA)-Derived Ligands2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Eur. J. Inorg. Chem. (8)

      Pages: 1143-1149

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 2-(β-C-glucopyranosyl)-b-amino acid: A new class of glycopeptide building block2007

    • Author(s)
      Y. Inaba
    • Journal Title

      Tetrahedron Lett. 48(6)

      Pages: 993-997

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Asymmetric Sulfur Atom Coordination in a Copper (II) Dipicolylamine (DPA) Complex with a Thioglycoside Ligand2007

    • Author(s)
      Y. Sugai
    • Journal Title

      Dalton Trans. (33)

      Pages: 3705-3709

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Quinoline-based tetradendate nitrogen ligands stabilize the bis (μ-oxo) dinuclear manganese (III,III) core2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Dalton Trans. (30)

      Pages: 3330-3334

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Regioselective modification of octaethylporphyrin to a phytoporphyrin derivative possessing 13^1-oxo group fixed on an exo-five-membered ring, similar to molecular structures of naturally occurring photoactive chlorophylls2007

    • Author(s)
      M. Kunieda
    • Journal Title

      J. Org. Chem. 72(19)

      Pages: 7398-7401

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Consideration of molecular arrangements in regio- and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Org. Biomol. Chem. 5

      Pages: 3834-3841

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Control of Intramolecular Oxygen Coordination in the Crystal Structure of the Copper(II) Complexes with Dipicolylamine (DPA)-Derived Ligands2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Eur. J. Marg. Chem 8

      Pages: 1143-1149

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Facile synthesis of 2-(β-C-glucopyranosyl)-β-amino acid: A new class of glycopeptide building block2007

    • Author(s)
      Y. Inaba
    • Journal Title

      Tetrahedron Lett 48(6)

      Pages: 993-997

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Asymmetric Sulfur Atom Coordination in a Copper(II) Dipicolylamine (DPA) Complex with a Thioglycoside Ligand2007

    • Author(s)
      Y. Sugai
    • Journal Title

      Dalton Transactions 33

      Pages: 3705-3709

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Quinoline-based tetradendate nitrogen ligands stabilize the bis(μ-oxo) dinuclear manganese(III,III) core2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Dalton Transactions 30

      Pages: 3330-3334

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Regioselective modification of octaethylporphyrin to a phytoporphyrin derivative possessing 13^1-oxo group fixed on an exo-five-membered ring, similar to molecular structures of naturally occurring photoactive chlorophylls2007

    • Author(s)
      M. Kunieda
    • Journal Title

      J. Org. Chem 72(19)

      Pages: 7398-7401

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Consideration of molecular arrangements in recto-and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation2007

    • Author(s)
      Y. Mikata
    • Journal Title

      Org. Biomol Chem 5

      Pages: 3834-3841

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Asymmetric Sulfur Atom Coordination in a Copper(II)Dipicolylamine(DPA)Complex with a Thioglycoside Ligand2007

    • Author(s)
      Y. Sugai, S. Fujii, T. Fujimoto, S. Yano and Y. Mikata
    • Journal Title

      Dalton Transactions

      Pages: 3705-3709

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Consideration of molecular arrangements in regio- and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation2007

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

      Org. Biomol. Chem.

      Pages: 3834-3841

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Control of Intramolecular Oxygen Coordination in the Crystal Structure of the Copper (II) Complexes with Dipicolylamine (DPA)-Derived Ligands2007

    • Author(s)
      Y.Mikata, T.Fujimoto, Y.Sugai, S.Yano
    • Journal Title

      Eur. J. Inorg. Chem. (8)

      Pages: 1143-1149

    • Related Report
      2006 Annual Research Report
  • [Journal Article] The Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors2006

    • Author(s)
      Y. Mikata
    • Journal Title

      Inorg. Chem. 45(23)

      Pages: 9262-9268

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] The Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors2006

    • Author(s)
      Y. Mikata
    • Journal Title

      Inorg. Chem 45(23)

      Pages: 9262-9268

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 不斉炭素および不斉酸素原子を含む金属錯体の合成と構造2008

    • Author(s)
      三方裕司
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] 不斉窒素および不斉酸素原子を含む金属錯体の合成と構造2008

    • Author(s)
      松田紗織
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] N-(2-ピリジルメチル)グリシン骨格を有する糖含有金属配位子の開発2008

    • Author(s)
      野口友華
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] メトキシキノリン部位を有するN,N'-ジメチルエチレンジアミン誘導体の亜鉛イオン選択的蛍光応答2007

    • Author(s)
      山下 梓
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 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2007

    • Author(s)
      山中あずさ
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシド結合を有する糖含有金属配位子の開発2007

    • Author(s)
      藤井祥子
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシド結合を有するβ-アラニン型糖アミノ酸を用いた糖ペプチドの合成と立体構造解析2007

    • Author(s)
      稲葉陽子
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] エーテル酸素原子が金属中心に配位した金属錯体の合成と構造2007

    • Author(s)
      藤本智美
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシド結合を有する糖含有金属錯体の開発2007

    • Author(s)
      藤井祥子
    • Organizer
      第57回錯体化学討論会
    • Place of Presentation
      名古屋工業大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] メトキシキノリン部位を有するN,N-ジメチルエチレンジアミン誘導体の亜鉛イオン選択的蛍光応答2007

    • Author(s)
      山下 梓
    • Organizer
      第57回錯体化学討論会
    • Place of Presentation
      名古屋工業大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 不斉窒素および不斉酸素原子を含む金属錯体の合成と構造2007

    • Author(s)
      松田沙織
    • Organizer
      第57回錯体化学討論会
    • Place of Presentation
      名古屋工業大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシルβ-アミノ酸を用いたβ-ペプチドの合成と立体構造解析2007

    • Author(s)
      稲葉陽子
    • Organizer
      第22回生体機能関連シンポジウム
    • Place of Presentation
      東北大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Conformational Analysis of β-Peptides Uitilizing C-Glycosyl β-Amino Acid2007

    • Author(s)
      稲葉陽子
    • Organizer
      第44回ペプチド討論会
    • Place of Presentation
      富山国際会議場
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] キノリン部位を有するN, N-ジメチルエチレンジアミン誘導体の亜鉛イオン選択的蛍光応答2007

    • Author(s)
      山下 梓
    • Organizer
      第40回酸化反応討論会
    • Place of Presentation
      奈良女子大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Coordination-Induced Oxygen Atom Chirality in the Complexes with Pyridine- and Quinoline-based Ligands2007

    • Author(s)
      三方裕司
    • Organizer
      14th International SPACC-CSJ Symposium
    • Place of Presentation
      National Taiwan University
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Conformational Analysis of β-Peptides Uitilizing C-Glycosyl β-Amino Acid2007

    • Author(s)
      Yoko, Inaba
    • Organizer
      44th Japanese Peptide Symposium
    • Place of Presentation
      Toyama, Toyama International Conference Center
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Coordination-Induced Oxygen Atom Chirality in the Complexes with Pyridine- and Quinoline-based Ligands2007

    • Author(s)
      Y. Mikata
    • Organizer
      14th International SPACC-CSJ Symposium
    • Place of Presentation
      Taipei, National Taiwan University
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシド結合を有する糖含有金属配位子の開発2006

    • Author(s)
      藤井祥子
    • Organizer
      第56回錯体化学討論会
    • Place of Presentation
      広島大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] エーテル酸素原子が金属中心に配位した金属錯体の合成と構造2006

    • Author(s)
      藤本智美
    • Organizer
      第56回錯体化学討論会
    • Place of Presentation
      広島大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] C-グリコシド結合を有するβ-アラニン型糖アミノ酸を用いたペプチド合成2006

    • Author(s)
      稲葉陽子
    • Organizer
      バイオ関連化学合同シンポジウム
    • Place of Presentation
      京都大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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