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Liquid-phase combinatorial synthesis of biologically active peptides utilizing fluorous tag

Research Project

Project/Area Number 20580115
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionMeijo University

Principal Investigator

MATSUGI Masato  名城大学, 農学部, 教授 (90324805)

Project Period (FY) 2008 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2011: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsフルオラス / 液相コンビナトリアル合成 / 生理活性 / ペプチド / フルオラスタグ / コンビナトリアル合成 / 液相 / ミクスチャー合成
Research Abstract

A study to carry out a concise liquid combinatorial synthesis of bioactive peptides, which was encoded by fluorous tag, was conducted. We have developed a highly active condensation reagent for peptides coupling, and a large-scale synthetic method of the fluorous protecting-reagent for amino acids. Furthermore, a synthetic route of Tenuecyclamide B from the N-terminus was established for the liquid mixture synthesis of the all stereoisomers.

Report

(6 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report   Self-evaluation Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (56 results)

All 2010 2009 2008 Other

All Journal Article (14 results) (of which Peer Reviewed: 13 results) Presentation (24 results) Book (3 results) Remarks (5 results) Patent(Industrial Property Rights) (10 results) (of which Overseas: 2 results)

  • [Journal Article] Synthesis and RCM reactions using a recyclable Grubbs-Hoveyda metathesis catalyst activated by a light-fluorous tag2010

    • Author(s)
      Masato Matsugi, Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, Takayuki Shioiri
    • Journal Title

      Journal of Organic Chemistry

      Volume: 75 Pages: 7905-7908

    • Related Report
      2011 Final Research Report 2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An effective synthesis of 5, 4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction2010

    • Author(s)
      Masato Matsugi, Masaki Takeda, Ayano Takahashi, Takahide Tazaki, Hiroto Tamura, Takayuki Shioiri
    • Journal Title

      Chemical Pharmaceutical Bulletin

      Volume: 58 Pages: 1107-1110

    • NAID

      130000299825

    • Related Report
      2011 Final Research Report 2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pronounced rate enhancements in condensation reactions attributed to the fluorous tag in modified Mukaiyama reagents2010

    • Author(s)
      Masato Matsugi, Shuichi Nakamura, Yoko Kunda, Yuaya Sugiyama, Takayuki Shioiri
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 133-135

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and RCM reactions using a recyclable Grubbs-Hoveyda metathesis catalyst activated by a light-fluorous tag2010

    • Author(s)
      Masato Matsugi, Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, Takayuki Shioiri
    • Journal Title

      Journal of Organic Chemistry 75

      Pages: 7905-7908

    • Related Report
      2010 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] An effective synthesis of 5, 4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction2010

    • Author(s)
      Masato Matsugi, Masaki Takeda, Ayano Takahashi, Takahide Tazaki, Hiroto Tamura, Takayuki Shioiri
    • Journal Title

      Chemical Pharmaceutical Bulletin 58

      Pages: 1107-1110

    • NAID

      130000299825

    • Related Report
      2010 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Pronounced rate enhancements in condensation reactions attributed to the fluorous tag in modified Mukaiyama reagents2010

    • Author(s)
      Masato Matsugi, Shuichi Nakamura, Yoko Kunda, Yuaya Sugiyama, Takayuki Shioiri
    • Journal Title

      Tetrahedron Letters 51

      Pages: 133-135

    • Related Report
      2010 Self-evaluation Report 2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A development of concise amidation and esterification reactions using amedium fluorous Mukaiyama reagent2009

    • Author(s)
      Masato Matsugi, Toshiya Hayashi, Shohei Haseba, Yoko Kunda
    • Journal Title

      Journal of Research Institute of Meijo University 8

      Pages: 123-128

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ライト及びミディアムフルオラスタグの特性を利用する有機合成反応2009

    • Author(s)
      松儀真人
    • Journal Title

      和光純薬時報 77

      Pages: 2-6

    • Related Report
      2009 Annual Research Report
  • [Journal Article] An Alternative and Facile Purification Procedure of Amidation and Esterification Reactions Using a Medium Fluorous Mukaiyama Reagent2008

    • Author(s)
      Masato Matsugi, Misaki Suganuma, Shoko Yoshida, Shohei Hasebe, Yoko Kunda, Kotaro Hagihara, Sayaka Oka
    • Journal Title

      Tetrahedron Letters

      Volume: 49 Pages: 6573-6574

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct Perfluoroalkylation of Non-activated Aromatic C-H bonds of Phenols2008

    • Author(s)
      Masato Matsugi, Masakazu Hasegawa, Shohei Hasebe, Shohei Takai, Ryusuke Suyama, Yusuke Wakita, Kanako Kudo, Hiromi Imamura, Toshiya Hayashi, Seiichi Haga
    • Journal Title

      Tetrahedron Letters

      Volume: 49 Pages: 4189-4191

    • NAID

      130006998750

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Alternative and Facile Purification Procedure of Amidation and Esterification Reactions Using a Medium Fluorous Mukaiyama Reagent2008

    • Author(s)
      Masato Matsugi, Misaki Suganuma, Shoko Yoshida, Shohei Hasebe, Yoko Kunda, Kotaro Hagihara, Sayaka Oka
    • Journal Title

      Tetrahedron Letters 49

      Pages: 6573-6574

    • Related Report
      2010 Self-evaluation Report 2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Perfluoroalkylation of Non-activated Aromatic C-H bonds of Phenols2008

    • Author(s)
      Masato Matsugi, Masakazu Hasegawa, Shohei Hasebe, Shohei Takai, Ryusuke Suyama, Yusuke Wakita, Kanako Kudo, Hiromi Imamura, Toshiya Hayashi, Seiichi Haga
    • Journal Title

      Tetrahedron Letters 49

      Pages: 4189-4191

    • NAID

      130006998750

    • Related Report
      2010 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Direct Perfluoroalkylation of Non-activated Aromatic C-H bonds of Phenols2008

    • Author(s)
      Masato Matsugi, Masakazu Hasegawa, Shohei Hasebe, Shohei Takai, Ryusuke Suyama, Yusuk Wakita, Kanako Kudo, Hiromi Imamura, Toshiya Hayashi, Seiichi Haga
    • Journal Title

      Tetrahedron Letters 49

      Pages: 4189-4191

    • NAID

      130006998750

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ライトフルオラスタグを基点とする有機反応プロセスの簡略化2008

    • Author(s)
      松儀 真人
    • Journal Title

      有機合成化学協会誌 66

      Pages: 694-704

    • NAID

      10021176095

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of Fluorous-FMOC Reagents and Application to Fluorous Mixture Synthesis of Biological Active Peptides2010

    • Author(s)
      Yuya Sugiyama, Yuki Kurata, Atsushi Miyazaki, Takayuki Shioiri, Masato Matsugi
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル
    • Year and Date
      2010-12-18
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of Fluorous-FMOC Reagents and Application to Fluorous Mixture Synthesis of Biological Active Peptides2010

    • Author(s)
      Yuya Sugiyama, Yuki Kurata, Atsushi Miyazaki, Takayuki Shioiri, Masato Matsugi
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル
    • Year and Date
      2010-12-18
    • Related Report
      2010 Self-evaluation Report
  • [Presentation] Synthesis of Fluorous-FMOC Reagents and Application to Fluorous Mixture Synthesis of Biological Active Peptides2010

    • Author(s)
      Yuya Sugiyama, Yuki Kurata, Atsushi Miyazaki, Takayuki Shioiri, Masato Matsugi
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM)
    • Place of Presentation
      Convention Center(ホノルル)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis and RCM Reaction Using a Recyclable Grubbs-Hoveyda Metathesis Catalyst Activated by a Light Fluorous Tag2010

    • Author(s)
      Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, Takayuki Shioiri, Masato Matsugi
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM)
    • Place of Presentation
      Convention Center(ホノルル)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] ライトフルオラスタグにより活性化されたGrubbs-Hoveyda触媒の合成と閉環メタセシス反応2010

    • Author(s)
      鈴村直紀・小林佑基・土屋勇輝・塩入孝之・松儀真人
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(名古屋市)
    • Year and Date
      2010-11-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] ミディアムフルオラス向山試薬を用いる環境調和型縮合反応2010

    • Author(s)
      薫田陽子・松井純子・塩入孝之・松儀真人
    • Organizer
      フルオラス科学研究会第3回シンポジウム
    • Place of Presentation
      長良川国際会議場(岐阜市)
    • Year and Date
      2010-10-08
    • Related Report
      2010 Annual Research Report
  • [Presentation] Fluorous Mixture Synthesisによる簡易ペプチド合成:フルオラスFMOC試薬の効率的合成と再生ルートの検討2010

    • Author(s)
      倉田雄基・杉山祐也・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2010サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2010-07-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] ライトフルオラスタグを基点とするTenuecyclamide B全立体異性体の簡易合成:Tenuecyclamide B効率的合成ルートの検討2010

    • Author(s)
      宮崎惇・林晃市・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2010サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2010-07-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] フルオラスタグと極性タグに基づく二次元展開TLC分離法の開発2010

    • Author(s)
      山田友里菜・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2010サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2010-07-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] ミディアムフルオラスストラテジーを基点とする向山試薬の改良と反応加速効果2010

    • Author(s)
      薫田陽子・塩入孝之・松儀真人
    • Organizer
      日本農芸化学会2010年度大会
    • Place of Presentation
      東京大学
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] Tenuecyclamide B 全立体異性体のフルオラスミクスチャー合成:フルオラスFMOC試薬及び Tenuecyclamide B 合成ルートの検討2010

    • Author(s)
      林晃市・大脇慎司・倉田雄基・宮崎惇・塩入孝之・松儀真人
    • Organizer
      日本農芸化学会2010年度大会
    • Place of Presentation
      東京大学
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] 高活性なリサイクル型ライトフルオラスメタセシス触媒の合成2010

    • Author(s)
      小林佑基・若月麻未・塩入孝之・松儀真人
    • Organizer
      日本農芸化学会2010年度大会
    • Place of Presentation
      東京大学
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] フルオラスタグにより活性化されたリサイクル型フルオラスメタセシス触媒の合成2009

    • Author(s)
      小林佑基・若月麻未・塩入孝之・松儀真人
    • Organizer
      フルオラス科学研究会第2回シンポジウム
    • Place of Presentation
      金沢市
    • Year and Date
      2009-11-27
    • Related Report
      2011 Final Research Report 2010 Self-evaluation Report
  • [Presentation] ライト及びミディアムフルオラスタグを基点とする有機合成2009

    • Author(s)
      松儀真人
    • Organizer
      第2回フルオラス科学研究会シンポジウム
    • Place of Presentation
      ITビジネスプラザ武蔵(金沢市)
    • Year and Date
      2009-11-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] ミディアムフルオラス向山試薬を用いる簡易縮合反応2009

    • Author(s)
      薫田陽子・萩原洸太郎・塩入孝之・松儀真人
    • 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 2010 Self-evaluation Report
  • [Presentation] ミディアムフルオラス向山試薬を用いる簡易縮合反応2009

    • Author(s)
      薫田陽子・萩原洸太郎・塩入孝之・松儀真人
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市文化ホール(金沢市)
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report
  • [Presentation] Fluorous Mixture Synthesisによる簡易ペプチド合成:フルオラスFMOC試薬合成とジペプチド保護体の分離検討2009

    • Author(s)
      杉山祐也・竹田匡輝・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2009サマーシンポジウム
    • Place of Presentation
      東京都
    • Year and Date
      2009-07-27
    • Related Report
      2011 Final Research Report
  • [Presentation] Fluorous Mixture Synthesis による簡易ペプチド合成:フルオラスFMOC試薬合成とジペプチド保護体の分離検討2009

    • Author(s)
      杉山祐也・竹田匡輝・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2009サマーシンポジウム
    • Place of Presentation
      東京都
    • Year and Date
      2009-07-27
    • Related Report
      2010 Self-evaluation Report
  • [Presentation] Fluorous Mixture Synthesis による簡易ペプチド合成:フルオラスFMOC試薬合成とジペプチド保護体の分離検討2009

    • Author(s)
      杉山祐也・竹田匡輝・塩入孝之・松儀真人
    • Organizer
      日本プロセス化学会2009サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 新規パーフルオロアルキル化反応を用いたフルオラスメタセシス触媒の簡易合成2009

    • Author(s)
      長谷部匠平・今村裕美・工藤加奈子・小林佑基・松儀真人
    • Organizer
      日本農芸化学会2009年度大会
    • Place of Presentation
      福岡市
    • Year and Date
      2009-03-29
    • Related Report
      2011 Final Research Report 2010 Self-evaluation Report
  • [Presentation] アンドロゲンアンタゴニスト活性作用を指向した5位及び4'位二置換型フラボン類の合成2009

    • Author(s)
      竹田匡輝, 岡沙弥佳, 小川善久, 吉岡麻衣子, 細田晃文, 田村廣人, 松儀真人
    • Organizer
      日本農芸化学会2009年度大会
    • Place of Presentation
      マリンメッセ博多
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 新規パーフルオロアルキル化反応を用いたフルオラスメタセシス触媒の簡易合成2009

    • Author(s)
      長谷部匠平, 今村裕美, 工藤加奈子, 小林佑基, 松儀真人
    • Organizer
      日本農芸化学会2009年度大会
    • Place of Presentation
      マリンメッセ博多
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 無保護フェノール類の芳香環炭素上への直接フルオラスタグ導入反応2008

    • Author(s)
      長谷部匠平, 竹田匡輝, 今村裕美, 工藤加奈子, 小林佑基, 松儀真人
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都テルサ
    • Year and Date
      2008-11-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] 低温ラジカル開始剤を用いた無保護フェノール類のパーフルオロアルキル化反応2008

    • Author(s)
      長谷部匠平, 竹田匡輝, 松儀真人
    • Organizer
      フルオラス科学研究会第1回シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Year and Date
      2008-10-23
    • Related Report
      2008 Annual Research Report
  • [Book] フルオラスケミストリーの基礎と応用2010

    • Author(s)
      松儀真人, Dennis P. Curran
    • Publisher
      シーエムシー出版
    • Related Report
      2011 Final Research Report
  • [Book] フルオラスケミストリーの基礎と応用2010

    • Author(s)
      松儀真人・Dennis P.Curran
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Self-evaluation Report
  • [Book] フルオラスケミストリーの基礎と応用,(担当部分:第3章)2010

    • Author(s)
      松儀真人・Dennis P.Curran
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www-agr.meijo-u.ac.jp/cgi-bin/labo13/index.html

    • Related Report
      2011 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://www-agr.meijo-u.ac.jp/cgi-bin/labo13/index.html

    • Related Report
      2010 Self-evaluation Report
  • [Remarks]

    • URL

      http://www-agr.meijo-u.ac.jp/cgi-bin/labo13/index.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www-agr.meijo-u.ac.jp/cgi-bin/labo13/index.html

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www-agr.meiio-u.ac.jp/labs/nn013/gyouseki.html

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] アンドロゲン受容体アンタゴニスト及びアンドロゲン受容体結合阻害剤2009

    • Inventor(s)
      松儀真人,田村廣人
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2009-206134
    • Filing Date
      2009-09-07
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] フルオラス縮合剤,フッ素成分の分離方法2009

    • Inventor(s)
      松儀真人
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2009-055318
    • Filing Date
      2009-03-09
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] アンドロゲン受容体アンタゴニスト及びアンドロゲン受容体結合阻害剤2009

    • Inventor(s)
      松儀真人・田村廣人
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2009-206134
    • Filing Date
      2009-09-07
    • Related Report
      2010 Self-evaluation Report
  • [Patent(Industrial Property Rights)] フルオラス縮合剤、フッ素成分の分離方法2009

    • Inventor(s)
      松儀真人
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2009-055318
    • Filing Date
      2009-03-09
    • Related Report
      2010 Self-evaluation Report 2008 Annual Research Report
  • [Patent(Industrial Property Rights)] アンドロゲン受容体アンタゴニスト及びアンドロゲン受容体結合阻害剤2009

    • Inventor(s)
      松儀真人, 田村廣人
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2009-206134
    • Filing Date
      2009-09-07
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] フェノール類芳香族炭素上への炭素-炭素結合形成方法2008

    • Inventor(s)
      松儀真人,芳賀聖一,林利哉
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2008-148753
    • Filing Date
      2008-06-06
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] Separation of Fluorous Compounds2008

    • Inventor(s)
      Dennis P. Curran, Masato Matsugi, Marvin S. Yu
    • Industrial Property Rights Holder
      University of Pittsburgh, Fluorous Technologies Inc
    • Acquisition Date
      2008-04-29
    • Related Report
      2011 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] フェノール類芳香族炭素上への炭素-炭素結合形成方法2008

    • Inventor(s)
      松儀真人、芳賀聖一、林利哉
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2008-148753
    • Filing Date
      2008-06-06
    • Related Report
      2010 Self-evaluation Report
  • [Patent(Industrial Property Rights)] Separation of Fluorous Compounds2008

    • Inventor(s)
      Dennis P.Curran, Masato Matsugi, Marvin S.Yu
    • Industrial Property Rights Holder
      University of Pittsburgh, Fluorous Technologies Inc.
    • Acquisition Date
      2008-04-29
    • Related Report
      2010 Self-evaluation Report
    • Overseas
  • [Patent(Industrial Property Rights)] フェノール類芳香族炭素上への炭素-炭素結合形成方法2008

    • Inventor(s)
      松儀真人 林利哉 芳賀聖一
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Number
      2008-148753
    • Filing Date
      2008-06-09
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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