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Design of proline analogues based on hybrid methods and their application

Research Project

Project/Area Number 21790018
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNational Institute of Health Sciences

Principal Investigator

DEMIZU Yosuke  National Institute of Health Sciences, 有機化学部, 研究官 (90389180)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsアミノ酸 / ペプチド / コンフォメーション / フォルダマー / ペプチド触媒
Research Abstract

The de novo design of peptides that fold into well-defined secondary structures is crucially important in a wide variety of fields such as organic chemistry, and biological and material sciences. Approaches to controlling the conformations of peptides have been studied, and as templates for stabilizing the secondary structures of peptides, α, α-disubstituted α-amino acids have been widely used. In this study, we demonstrated the synthesis of proline analogues and stabilized short helical peptides, and their application to the enantioselective epoxidation of (E)-chalcone.

Report

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

    (62 results)

All 2011 2010 2009 Other

All Journal Article (32 results) (of which Peer Reviewed: 28 results) Presentation (22 results) Remarks (2 results) Patent(Industrial Property Rights) (6 results)

  • [Journal Article] Design of a stabilized short helical peptide and its application to catalytic enantioselective epoxidation of (E)-chalcone2011

    • Author(s)
      N.Yamagata, Y.Demizu, Y.Sato, M.Doi, M.Tanaka, K.Nagasawa, H.Okuda, M.Kurihara
    • Journal Title

      Tetrahedron Lett. 52

      Pages: 798-801

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of stereoisomers of the non-secosteroidal ligand LG190178 and their evaluation using the mutant vitamin D receptor2011

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      Lett.Org.Chem.

      Volume: 8 Pages: 43-47

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of a stabilized short helical peptide and its application to catalytic enantioselective epoxidation of (E)-chalcone2011

    • Author(s)
      N.Yamagata, et al.
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 798-801

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformational studies on peptides containing α,α-disubstituted α-amino acids : chiral cyclic α,α-disubstituted α-amino, acid as an α-helical inducer2011

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      Org.Biomol.Chem.

      Volume: 9 Pages: 3303-3312

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of one D-Leu residue on right-handed helical -L-Leu-Aib- peptides in the crystal state2011

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      J.Pept.Sci.

      Volume: 17 Pages: 420-426

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Three-dimensional structure control of diastereomeric Leu-Leu-Aib-Leu-Leu-Aib sequences in the solid state2010

    • Author(s)
      Y.Demizu, M.Doi, Y.Sato, M.Tanaka, H.Okuda, M.Kurihara
    • Journal Title

      J.Org.Chem. 75

      Pages: 5234-5239

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conformations of peptides containing a chiral cyclic-α,α-disubstituted α-amino acid within the sequence of Aib residues2010

    • Author(s)
      Y.Demizu, M.Tanaka, M.Doi, M.Kurihara, H.Okuda, H.Suemune
    • Journal Title

      J.Pept.Sci. 16

      Pages: 621-626

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols2010

    • Author(s)
      M.Kuriyama, S.Tanigawa, Y.Kubo, Y.Demizu, O.Onomura
    • Journal Title

      Tetrahedron : Asymmetry 21

      Pages: 1370-1373

    • NAID

      120006984560

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solid-state conformation of diastereomeric -Pro-Pro-(Aib)_4 sequences2010

    • Author(s)
      M.Oba, Y.Demizu, N.Yamagata, Y.Sato, M.Doi, M.Tanaka, H.Suemune, H.Okuda, M.Kurihara
    • Journal Title

      Tetrahedron 66

      Pages: 2293-2296

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Controlling the helical screw sense of peptides with C-terminal L-valine2010

    • Author(s)
      Y.Demizu, N.Yamagata, Y.Sato, M.Doi, M.Tanaka, H.Okuda, M.Kurihara
    • Journal Title

      J.Pept.Sci. 16

      Pages: 153-158

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Computational study on helical structure of chiralα,α-disubstituted oligopeptides2010

    • Author(s)
      M.Kurihara, Y.Sato, N.Yamagata, Y.Demizu, H.Okuda, M.Nagano, M.Doi, M.Tanaka, H.Suemune
    • Journal Title

      Peptide Science 2009

      Pages: 385-386

    • Related Report
      2010 Final Research Report
  • [Journal Article] Controlling the helical screw sense of peptides by N-terminal proline2010

    • Author(s)
      N.Yamagata, Y.Demizu, Y.Sato, M.Oba, M.Tanaka, M.Doi, K.Nagasawa, H.Suemune, H.Okuda, M.Kurihara
    • Journal Title

      Peptide Science 2009

      Pages: 383-384

    • Related Report
      2010 Final Research Report
  • [Journal Article] Conformational analysis of water-soluble oligopeptides composed of chiral cyclicα,α-disubstitutedα,-amino acids2010

    • Author(s)
      Y.Demizu, M.Tanaka, H.Suemune, M.Doi, Y.Sato, H.Okuda, M.Kurihara
    • Journal Title

      Peptide Science 2009

      Pages: 381-382

    • Related Report
      2010 Final Research Report
  • [Journal Article] Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols2010

    • Author(s)
      M.Kuriyama, et al.
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 21 Pages: 1370-1373

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformations of peptides containing a chiral cyclic α,α-disubstituted α-amino acid within the sequence of Aib residues2010

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      J.Pept.Sci.

      Volume: 16 Pages: 621-626

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Three-dimensional structure control of diastereomeric Leu-Leu-Aib-Leu-Leu-Aib sequences in the solid state2010

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      J.Org.Chem.

      Volume: 75 Pages: 5234-5239

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-state confornlation of diastereomeric -Pro-Pro-(Aib)_4 sequences2010

    • Author(s)
      M.Oba, et al.
    • Journal Title

      Tetrahedron 66

      Pages: 2293-2296

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Controlling the helical screw sense of peptides with C-terminal L-valine2010

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      J.Pept.Sci. 16

      Pages: 153-158

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Non-enzymatic kinetic resolution of racemic alpha-hydroxyalkanephosphonates with chiral copper catalyst2009

    • Author(s)
      Y.Demizu, A.Moriyama, O.Onomura
    • Journal Title

      Tetrahedron Lett.<Highlighted by Synfacts 1126 (2009)> 37

      Pages: 5241-5244

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Helical-screw directions of diastereoisomeric cyclic α-amino acid oligomers2009

    • Author(s)
      M.Nagano, M.Tanaka, M.Doi, Y.Demizu, M.Kurihara, H.Suemune
    • Journal Title

      Org.Lett. 11

      Pages: 1135-1137

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct electrochemical α-cyanation of N-protected cyclic amines, S. S. Libendi2009

    • Author(s)
      Y.Demizu, O.Onomura
    • Journal Title

      Org.Biomol.Chem. 7

      Pages: 351-356

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ring contraction of α,β-unsaturated cyclic amines with cis-dihydroxylation at the α,β-position,S.2009

    • Author(s)
      S.Libendi, Y.Demizu, Y.Matsumura, O.Onomura
    • Journal Title

      Heterocycles 77

      Pages: 311-321

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Computational study on helical structure of α,α-disubstituted oligopeptides containing chiral α-amino acids2009

    • Author(s)
      M.Kurihara, Y.Sato, N.Yamagata, H.Okuda, M.Nagano, Y.Demizu, M.Doi, M.Tanaka, H.Suemune
    • Journal Title

      Peptide Science 2008

      Pages: 149-150

    • NAID

      10027166112

    • Related Report
      2010 Final Research Report
  • [Journal Article] Non-enzymatic kinetic resolut with chiral conner catalvstion of racemic α-hydroxyalkanephosphonates2009

    • Author(s)
      Y.Demizu, et al.
    • Journal Title

      Tetrahedron Lett. 37

      Pages: 5241-5244

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helical-screw directions of diastereoisomeric cyclic α-amino acid oligomers2009

    • Author(s)
      M.Nagano, et al.
    • Journal Title

      Org. Lett. 11

      Pages: 1135-1137

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct electrochemical α-cyanation of N-protected cyclic amines2009

    • Author(s)
      S.S.Libendi, et al.
    • Journal Title

      Org. Biomol. Chem. 7

      Pages: 351-356

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring contraction of α,β-unsaturated cyclic amines with cis-dihydroxylation at the α,β-position2009

    • Author(s)
      S.S.Libendi, et al.
    • Journal Title

      Heterocycles 77

      Pages: 311-321

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Computational study on helical structure of α,α-disubstituted oligopeptides containing chiral α-amino acids2009

    • Author(s)
      M.Kurihara, et al.
    • Journal Title

      Peptide Science 2008

      Pages: 149-150

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformational studies on peptides containing α,α-disubstituted α-amno acids : chiral cyclic ,α,α-disubstituted α-amino acidas an α-helical inducer

    • Author(s)
      Y.Demizu, M.Doi, M.Kurihara, H.Okuda, M.Nagano, H.Suemune, M.Tanaka
    • Journal Title

      Org. Biomol.Chem. (in press)

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solid-phase nucleophilic fluorination

    • Author(s)
      Y.Demizu, K.Sano, N.Terayama, W.Hakamata, Y.Sato, H.Inoue, H.Okuda, M.Kurihara
    • Journal Title

      Synth. Commun. (in press)

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of stereoisomers of the non-secosteroidal ligand LG190178 and their evaluation using the mutant vitamin D receptor

    • Author(s)
      Y.Demizu, A.Nakatsu, S.Honzawa, A.Yamashita, T.Sugiura, A.Kittaka, S.Kato, H.Okuda, M.Kurihara
    • Journal Title

      Lett.Org.Chem. (in press)

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Effect of one D-Leu residue on right-handed helical -L-Leu-Aib- peptides in the crystal state, Y. Demizu

    • Author(s)
      M.Doi, Y.Sato, M.Tanaka, H.Okuda, M.Kurihara
    • Journal Title

      J.Pept.Sci. (in press.)

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Presentation] ヘリカルペプチドの制御とカルコン類の不斉エポキシ化への応用2011

    • Author(s)
      出水庸介, 山縣奈々子, 佐藤由紀子, 土井光暢, 田中正一, 奥田晴宏, 栗原正明
    • Organizer
      日本薬学会第131回年会
    • Place of Presentation
      静岡
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Controlling the helical screw sense of Aib-based peptides with chiral α-amino acids2010

    • Author(s)
      Y.Demizu
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      ハワイ
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Conformational studies of diastereomeric -Leu-Aib- peptides2010

    • Author(s)
      Y.Demizu
    • Organizer
      5th International Peptide Symposium
    • Place of Presentation
      京都
    • Year and Date
      2010-12-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] ノンセコVDRリガンドの創製と結合様式の解析2010

    • Author(s)
      出水庸介
    • Organizer
      第29回メディシナルケミストリーシンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2010-11-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Structural control of diastereomeric Leu-Leu-Aib-Leu-Leu-Aib sequences2010

    • Author(s)
      Y.Demizu
    • Organizer
      31st European Peptide Symposium
    • Place of Presentation
      デンマーク
    • Year and Date
      2010-09-07
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新たな水素結合ネットワークを指向したVDRリガンド2010

    • Author(s)
      出水庸介
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      東京
    • Year and Date
      2010-05-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Development of non-secosteroidal VDR ligands2010

    • Author(s)
      Y.Demizu
    • Organizer
      The 21st French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2010-05-10
    • Related Report
      2010 Annual Research Report
  • [Presentation] C末端バリンによるヘリカル二次構造の制御2010

    • Author(s)
      出水庸介
    • Organizer
      日本薬学会第130回年会
    • Place of Presentation
      岡山桃太郎アリーナ(岡山)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Conformational studies of diastereomeric-Leu-Aib-peptides2010

    • Author(s)
      Demizu, Y., Doi, M., Sato, Y., Tanaka, M., Okuda, H., Kurihara, M
    • Organizer
      5th International Peptide Symposium
    • Place of Presentation
      Kyoto
    • Related Report
      2010 Final Research Report
  • [Presentation] Controlling the helical screw sense of Aib-based peptides with chiral a-amino acids2010

    • Author(s)
      Demizu, Y., Sato, Y., Tanaka, M, Doi, M, Suemune, H, Okuda, H, Kurihara, M
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Honolulu, USA
    • Related Report
      2010 Final Research Report
  • [Presentation] ノンセコVDRリガンドの創製と結合様式の解析2010

    • Author(s)
      出水庸介, 佐藤由紀子, 落合鋭士, 堀江恭平, 高木健一郎, 角田真二, 上村みどり, 奥田晴宏, 栗原正明
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2010 Final Research Report
  • [Presentation] Structural control of diastereomeric Leu-Leu-Aib-Leu-Leu-Aib sequences2010

    • Author(s)
      Demizu, Y, Doi, M, Sato, Y, Tanaka, M, Okuda, H Kurihara, M
    • Organizer
      31st European Peptide Symposium
    • Place of Presentation
      Copenhagen, Denmark
    • Related Report
      2010 Final Research Report
  • [Presentation] Development of non-secosteroidal VDR ligands2010

    • Author(s)
      Demizu, Y, Sato, Y, Ochiai, E, Horie, K, Kakua, S, Takimoto-Kamimura, M, Okuda, H, Kurihara, M
    • Organizer
      The 21st French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2010 Final Research Report
  • [Presentation] 新たな水素結合ネットワークを指向したVDRリガンド2010

    • Author(s)
      出水庸介, 佐藤由紀子, 竹内由起, 落合鋭士, 堀江恭平, 角田真二, 上村みどり, 奥田晴宏, 栗原正明
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      横浜
    • Related Report
      2010 Final Research Report
  • [Presentation] ヘリカルオリゴマーによるα,β-不飽和ケトンの不斉エポキシ化2010

    • Author(s)
      出水庸介, 田中正一
    • Organizer
      「協奏機能触媒」第7回公開シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2010 Final Research Report
  • [Presentation] C末端バリンによるヘリカル二次構造の制御2010

    • Author(s)
      出水庸介, 佐藤由紀子, 土井光暢, 田中正一, 奥田晴宏, 栗原正明
    • Organizer
      日本薬学会第130回年会
    • Place of Presentation
      岡山
    • Related Report
      2010 Final Research Report
  • [Presentation] ノンセコステロイド型VDRリガンドの設計と合成2009

    • Author(s)
      出水庸介
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京大学(東京)
    • Year and Date
      2009-11-25
    • Related Report
      2009 Annual Research Report
  • [Presentation] ノンセコステロイド型VDRリガンドのデノボ設計2009

    • Author(s)
      出水庸介
    • 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(石川)
    • Year and Date
      2009-11-16
    • Related Report
      2009 Annual Research Report
  • [Presentation] 水溶性キラル環状α,α-ジ置換アミノ酸およびペプチドの合成とコンフォメーション解析2009

    • Author(s)
      出水庸介
    • Organizer
      第46回ペプチド討論会
    • Place of Presentation
      北九州国際会議場(福岡)
    • Year and Date
      2009-11-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] ノンセコステロイド型VDRリガンドの設計と合成2009

    • Author(s)
      出水庸介, 金子文也, 岩井すみれ, 高橋健男, 佐藤由紀子, 落合鋭士, 堀江恭平, 角田真二, 上村みどり, 奥田晴宏, 栗原正明
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2010 Final Research Report
  • [Presentation] ノンセコステロイド型VDRリガンドのデノボ設計2009

    • Author(s)
      出水庸介, 金子文也, 岩井すみれ, 高橋健男, 佐藤由紀子, 落合鋭士, 堀江恭平, 角田真二, 上村みどり, 奥田晴宏, 栗原正明
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Related Report
      2010 Final Research Report
  • [Presentation] 水溶性キラル環状α,α-ジ置換アミノ酸およびペプチドの合成とコンフォメーション解析2009

    • Author(s)
      出水庸介, 田中正一, 末宗洋, 土井光暢, 佐藤由紀子, 奥田晴宏, 栗原正明
    • Organizer
      第46回ペプチド討論会
    • Place of Presentation
      北九州
    • Related Report
      2010 Final Research Report
  • [Remarks] 2010年有機合成化学協会 研究企画賞(カネカ)受賞

    • Related Report
      2010 Final Research Report
  • [Remarks] 高度に空間制御されたペプチドフォルダマーを利用した不斉有機触媒の開発

    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] ラムノシドエステル誘導体およびその製造方法2010

    • Inventor(s)
      尾野村治、出水庸介、久保裕紀、岩崎史哲
    • Industrial Property Rights Holder
      尾野村治、出水庸介、久保裕紀、岩崎史哲
    • Patent Publication Number
      2010-030916
    • Acquisition Date
      2010-02-12
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミノ酸エステル誘導体,および光学活性アミノアセタール誘導体の製造方法2009

    • Inventor(s)
      尾野村治、出水庸介、山本博将
    • Industrial Property Rights Holder
      尾野村治、出水庸介、山本博将
    • Patent Publication Number
      2009-227594
    • Acquisition Date
      2009-10-08
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] キシロシドエステル誘導体およびその製造方法2009

    • Inventor(s)
      尾野村治、出水庸介、岩崎史哲
    • Industrial Property Rights Holder
      尾野村治、出水庸介、岩崎史哲
    • Patent Publication Number
      2009-227610
    • Acquisition Date
      2009-10-08
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] グルコシドエステル誘導体およびその製造方法2009

    • Inventor(s)
      尾野村治、出水庸介、岩崎史哲
    • Industrial Property Rights Holder
      尾野村治、出水庸介、岩崎史哲
    • Patent Publication Number
      2009-221161
    • Acquisition Date
      2009-10-01
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] ピラノシドエステル化合物およびその製造方法2009

    • Inventor(s)
      尾野村治、出水庸介、岩崎史哲
    • Industrial Property Rights Holder
      尾野村治、出水庸介、岩崎史哲
    • Patent Publication Number
      2009-215175
    • Acquisition Date
      2009-09-24
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性α-スルポニルオキシカルボン酸アミド誘導体及びそれらの製造方法2009

    • Inventor(s)
      尾野村治、出水庸介、岩崎史哲
    • Industrial Property Rights Holder
      尾野村治、出水庸介、岩崎史哲
    • Patent Publication Number
      2009-091327
    • Acquisition Date
      2009-04-30
    • Related Report
      2009 Annual Research Report

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

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