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Construction of CD-Sensitive Porphyrin Tweezer Systems and Their Application for the Direct Sensing of Chiral Organic Molecules

Research Project

Project/Area Number 21590027
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

TAKANAMI Toshikatsu  明治薬科大学, 薬学部, 教授 (40241111)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2011: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsビスポルフィリン / 円二色性 / 絶対配置 / ホスト分子 / 超分子 / 分散型CDスペクトル / CD励起子法 / 不斉認識 / レセプター分子 / 不斉認識能 / SNAr反応 / 光学活性アミン / 分散性CDスペクトル / 絶対配置決定 / 光学活性アルコール / 非対応称ポルフィリン / 根岸クロスカップリング / 光学活性ジアミン / 光学活性ジオール / 非対称ポルフィリン
Research Abstract

Design, synthesis, and chirogenetic properties of novel pseudo-cofacial zinc porphyrin tweezers as an efficient circular dichroism(CD)-sensitive host molecule were explored. The notable features of the new tweezer systems are their facile synthetic accessibility and high binding affinity for a variety of optically active molecules, including diols, alcohols, and epoxides as well as amines, diamines, and aminoalcohols, providing an efficient direct, non-empirical determination of absolute configuration of these substrates at room temperature without the need for chemical derivatization.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (40 results)

All 2012 2011 2010 2009 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (22 results) Book (3 results) Remarks (4 results)

  • [Journal Article] An Efficient One-Pot Protocol for Asymmetric Bifunctionalization of 5, 15-Disubstituted Porphyrins : Direct Access to meso Activated Alkenyl-Substituted meso-Formylporphyrins2011

    • Author(s)
      T. Takanami, S. Hayashi, K. Iso, J. Matsumoto, F. Hino
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Issue: 41 Pages: 5345-5348

    • DOI

      10.1016/j.tetlet.2011.08.025

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Efficient One-Pot Procedure for Asymmetric Bifunctionalization of 5, 15-Disubstituted Porphyrins : A Simple Preparation of meso Acyl-, Alkoxycarbonyl-, and Carbamoyl-Substituted meso-Formylporphyrins2009

    • Author(s)
      T. Takanami, A. Wakita, J. Matsumoto, S. Sekine, K. Suda
    • Journal Title

      Chem. Commun

      Issue: 1 Pages: 101-103

    • DOI

      10.1039/b817551a

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Metallophthalocyanine Complex, Cr(TBPC)-OTf : An Efficient, Recyclable Lewis Acid Catalyst in the Regio-and Stereoselective Rearrangement of Epoxides to Aldehydes2009

    • Author(s)
      K. Suda, S. Nakajima, Y. Satoh, T. Takanami
    • Journal Title

      Chem. Commun

      Issue: 10 Pages: 1255-1257

    • DOI

      10.1039/b820948k

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] One-Pot Preparation of meso-Hydroxymethylporphyrins via a Sequential S_NAr Reaction with(2-Pyridyldimethylsilyl) methyllithium Followed by Hydrolysis and Aerobic Oxidation2009

    • Author(s)
      T. Takanami, J. Matsumoto, Y. Kumagai, A. Sawaizumi, K. Suda, A Facile
    • Journal Title

      Tetrahedron Lett

      Volume: 50 Issue: 1 Pages: 68-70

    • DOI

      10.1016/j.tetlet.2008.10.087

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly Regioselective Rearrangement of 2, 3-Diaryloxiranes into 2, 2-Diarylacetaldehydes Catalyzed by Ytterbium Porphyrin Complex, Yb(TPP) OTf2009

    • Author(s)
      T. Takanami, S. Nakajima, S. Nakadai, F. T. Takanami, S. Nakajima, S. Nakadai, F. Hino, K. Suda
    • Journal Title

      Heterocycles

      Volume: 77 Issue: 1 Pages: 365-374

    • DOI

      10.3987/com-08-s(f)27

    • NAID

      40016405879

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] 特異な反応場を持つルイス酸触媒としての金属ポルフィリンおよびフタロシアニン錯体2009

    • Author(s)
      高波利克、須田晃治
    • Journal Title

      有機合成化学協会誌

      Volume: 67 Pages: 595-605

    • NAID

      10024969268

    • URL

      https://www.jstage.jst.go.jp/browse/yukigoseikyokaishi/67/6/_contents/-char/ja/

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Efficient One-Pot Procedure for Asymmetric Bifunctionalization of 5,15-Disubstituted Porphyrins : A Simple Preparation of meso Acyl-, Alkoxycarbonyl-, and Carbamoyl-Substituted meso-Formylporphyrins2009

    • Author(s)
      高波利克
    • Journal Title

      Chem.Commun. 2009

      Pages: 101-103

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metallophthalocyanine Complex, Cr(TBPC)OTf : An Efficient, Recyclable Lewis Acid Catalyst in the Regio- and Stereoselective Rearrangement of Epoxides to Aldehydes2009

    • Author(s)
      Suda K
    • Journal Title

      Chem.Commun. 2009

      Pages: 1255-1257

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Facile One-Pot Preparation of meso-Hydroxymethylporphyrins via a Sequential S_NAr Reaction with(2-Pyridyldimethylsilyl)methyllithium Followed by Hydrolysis and Aerobic Oxidation2009

    • Author(s)
      高波利克
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 68-70

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Regioselective Rearrangement of 2,3-Diaryloxiranes into 2,2-Diaryl-acetaldehydes Catalyzed by Yitterbium Porphyrin Complex, Yb(TPP)OTf2009

    • Author(s)
      高波利克
    • Journal Title

      Heterocycles 77

      Pages: 365-374

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 特異な反応場を持つルイス酸触媒としての金属ポルフィリンおよびフタロシアニン錯体2009

    • Author(s)
      高波利克
    • Journal Title

      有機合成化学協会誌 67

      Pages: 595-605

    • NAID

      10024969268

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] フッ素官能基を持つ対面型ポルフィリン二量体の超分子円二色性を利用する化合物の非破壊的絶対配置決定2012

    • Author(s)
      林賢、高波利克
    • Organizer
      第10回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪府吹田市
    • Year and Date
      2012-05-12
    • Related Report
      2011 Final Research Report
  • [Presentation] Pd触媒を用いたハロゲン化ポルフィリンとR_3Si-CH_2MgXとの熊田カップリング:シリルメチルポルフィリンの合成2012

    • Author(s)
      杉田典昭、林賢、高波利克
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌市
    • Year and Date
      2012-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] An Efficient Preparation of meso Activated Alkenyl-Substituted meso-Formylporphyrins using a One-Pot Asymmetric Bifunctionalization of 5, 15-Disubstituted Porphyrins2011

    • Author(s)
      S. Hayashi, K. Iso, J. Matsumoto, F. Hino, T. Takanami
    • Organizer
      The 8th AFMC International Medicinal Chemistry Symposium(AIMECS11)
    • Place of Presentation
      Tokyo, Japan
    • Year and Date
      2011-12-01
    • Related Report
      2011 Final Research Report
  • [Presentation] An Efficient Preparation of meso Activated Alkenyl-Substituted meso-Formyl porphyrins using a One-Pot Asymmetric Bifunctionalization of 5,15-Disubstituted Porphyrins2011

    • Author(s)
      Hayashi S, Iso K, Matsumoto J, Hino F, Takanami T
    • Organizer
      e 8th AFMC International Medicinal Chemistry Symposium (AIMECS
    • Place of Presentation
      東京
    • Year and Date
      2011-12-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] 対面型ポルフィリン二量体の構築とその超分子CD励起子キラリティー法への応用2011

    • Author(s)
      林賢、岡田実、四倉未来、高波利克
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島市
    • Year and Date
      2011-11-08
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] フッ素官能基を持つ対面型ポルフィリン二量体の構築とその不斉認識能2011

    • Author(s)
      林賢、直江紗織、堀田美穂、大村慶一、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] 熊田カップリングを用いたポルフィリンの修飾反応2011

    • Author(s)
      杉田典昭、林賢、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] チオウレアをリンカー部分に含むポルフィリン二量体の構築2011

    • Author(s)
      直江紗織、林賢、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] フッ素官能基を持つ対面型ポルフィリン二量体の構築とその不斉認識能2011

    • Author(s)
      林賢、直江紗織、堀田美穂、大村慶一、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Annual Research Report 2010 Annual Research Report
  • [Presentation] 熊田カップリングを用いたポルフィリンの修飾反応2011

    • Author(s)
      杉田典昭、林賢、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] チオウレアをリンカー部分に含むポルフィリン二量体の構築2011

    • Author(s)
      直江紗織、林賢、高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Annual Research Report 2010 Annual Research Report
  • [Presentation] パラジウム触媒を用いたGrignard試薬とポルフィリンとのカップリング反応2011

    • Author(s)
      杉田典昭, 林賢, 高波利克
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] メソ位を鎖状構造で連結した対面型ポルフィリン二量体の構築とその分子認識能2010

    • Author(s)
      林賢, 四倉未来, 魚住亜祐美, 高波利克
    • Organizer
      第60回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟市
    • Year and Date
      2010-12-04
    • Related Report
      2011 Final Research Report
  • [Presentation] メソ位を鎖状構造で連結した対面型ポルフィリン二量体の構築とその分子認識能2010

    • Author(s)
      林賢, 四倉未来, 魚住亜祐美, 高波利克
    • Organizer
      第60回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2010-12-04
    • Related Report
      2010 Annual Research Report
  • [Presentation] Metalloporphyrins and Phthalocyanines as Efficient Lewis Acid Catalysts with a Unique Reaction-Field2010

    • Author(s)
      T. Takanami
    • Organizer
      6th International Conference on Porphyrins and Phthalocyanies(ICPP-6)
    • Place of Presentation
      Santa Ana Pueblo, New Mexico, USA
    • Year and Date
      2010-07-09
    • Related Report
      2011 Final Research Report
  • [Presentation] Metalloporphyrins and Phthalocyanines as Efficient Lewis Acid Catalysts with a Unique Reaction-Field2010

    • Author(s)
      Toshikatsu Takanami
    • Organizer
      6th International Conference on Porphyrins and Phthalocyanies (ICPP-6)
    • Place of Presentation
      Santa Ana Pueblo, New Mexico, USA
    • Year and Date
      2010-07-09
    • Related Report
      2010 Annual Research Report
  • [Presentation] 熊田カップリングを用いたポルフィリンの修飾反応2010

    • Author(s)
      魚住亜祐美、新海梓、高波利克
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山市
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] エノン類共存下でのポルフィリンとシリルメチルリチウム反応剤とのS_NAr反応:エノン構造とホルミル構造を持つ非対称ポルフィリンのone-pot合成2009

    • Author(s)
      松本純、磯和宏、澤泉青代、高波利克
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市
    • Year and Date
      2009-11-17
    • Related Report
      2011 Final Research Report
  • [Presentation] エノン類共存下でのポルフィリンとシリルメチルリチウム反応剤とのS_NAr反応:エノン構造とホルミル構造を持つ非対称ポルフィリンの one-pot 合成2009

    • Author(s)
      高波利克
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report
  • [Presentation] 対面型ポルフィリン二量体の構築及び超分子CD励起子キラリティー法への応用2009

    • Author(s)
      魚住亜祐美、四倉未来、高波利克
    • Organizer
      第26回有機合成化学セミナー
    • Place of Presentation
      前橋市
    • Year and Date
      2009-09-16
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] Exploration of the Reaction of(2-Pyridyldimethylsilyl) methyllithium with Porphyrins : A Simple Preparation for meso-Formyl-and meso-Hydroxymethylporphyrins2009

    • Author(s)
      T. Takanami, A. Sawaizumi, A. Wakita, J. Matsumoto, K. Suda
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2009-09-16
    • Related Report
      2011 Final Research Report
  • [Presentation] Exploration of the Reaction of(2-Pyridyldimethylsilyl)methyllithium with Porphyrins : A Simple Preparation for meso-Formyl- and meso-Hydroxymethyl-porphyrins2009

    • Author(s)
      高波利克
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      京都市
    • Year and Date
      2009-09-16
    • Related Report
      2009 Annual Research Report
  • [Book] 薬学用語辞典(日本薬学会編)2012

    • Author(s)
      高波利克
    • Publisher
      東京化学同人
    • Related Report
      2011 Final Research Report
  • [Book] スタンダード薬学シリーズ(日本薬学会編)2011

    • Author(s)
      高波利克
    • Publisher
      東京化学同人
    • Related Report
      2011 Final Research Report
  • [Book] スタンダード薬学シリーズ2「物理系薬学-I.物質の物理的性質」第2版2011

    • Author(s)
      高波利克(分担:日本薬学会編)
    • Publisher
      東京化学同人
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.my-pharm.ac.jp/~physchem/

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.my-pharm.ac.jp/~physchem/

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.my-pharm.ac.jp/~physchem/

    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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