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Design and synthesis of peptide foldamer using alpha,alpha-disubstituted alpha-amino acids

Research Project

Project/Area Number 18K14870
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionNagasaki University

Principal Investigator

UEDA Atsushi  長崎大学, 医歯薬学総合研究科(薬学系), 准教授 (10732315)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsジ置換アミノ酸 / ペプチド / 有機分子触媒 / 薬学 / 有機化学 / フッ素
Outline of Final Research Achievements

Synthesis of α,α-disubstituted α-amino acids and their peptides were performed. Secondary structural analysis of these peptides could be useful for design of peptide foldamers. α-Trifluoromethylated α,α-disubstituted α-amino acids were synthesized with a variety of side chains. Optical resolution of these amino acids were achieved by chromatographic separation of the corresponding (R)-BINOL ester derivative. We also synthesized α-amino acids possessing rare sugar on their side chain. Simplification of peptide catalyst structure resulted in high catalytic activity, which is important from the point of green sustainability.

Academic Significance and Societal Importance of the Research Achievements

生体内で重要な役割を担うペプチドは、機能性分子としての高いポテンシャルを有している。今回フッ素を導入したペプチドにより、バイオアベイラビリティーの増大が期待でき、また一方で、希少糖を導入したアミノ酸を今後ペプチドへ導入していくことで、生体内リガンドとしての可能性も高まる。ペプチド触媒の簡素化による触媒活性の向上は、化合物のロスを減らし、グリーンサスティナビリティの向上に資する結果と考えられる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (45 results)

All 2021 2020 2019 2018

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 2 results) Presentation (36 results) (of which Int'l Joint Research: 11 results,  Invited: 1 results)

  • [Journal Article] Synthesis of Chiral α‐Trifluoromethyl α,α‐Disubstituted α‐Amino Acids and Conformational Analysis of L‐Leu‐Based Peptides with ( R )‐ or ( S )‐α‐Trifluoromethylalanine2020

    • Author(s)
      Ueda Atsushi、Ikeda Misuzu、Kasae Takuya、Doi Mitsunobu、Demizu Yosuke、Oba Makoto、Tanaka Masakazu
    • Journal Title

      ChemistrySelect

      Volume: 5 Issue: 35 Pages: 10882-10886

    • DOI

      10.1002/slct.202002888

    • NAID

      120006988512

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling2020

    • Author(s)
      Ueda Atsushi、Higuchi Mei、Sato Kazuki、Umeno Tomohiro、Tanaka Masakazu
    • Journal Title

      Molecules

      Volume: 25 Issue: 20 Pages: 4667-4667

    • DOI

      10.3390/molecules25204667

    • NAID

      120006988483

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose2020

    • Author(s)
      Ueda Atsushi、Pi Jinhong、Makura Yui、Tanaka Masakazu、Uenishi Jun'ichi
    • Journal Title

      RSC Advances

      Volume: 10 Issue: 16 Pages: 9730-9735

    • DOI

      10.1039/d0ra01033b

    • NAID

      120006988253

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] α-Selective glycosidation of d-tagatofuranose with a 3,4-O-isopropylidene protection2019

    • Author(s)
      Makura Yui、Ueda Atsushi、Matsuzaki Takashi、Minamino Tetsuo、Tanaka Masakazu
    • Journal Title

      Tetrahedron

      Volume: 75 Issue: 27 Pages: 3758-3766

    • DOI

      10.1016/j.tet.2019.05.052

    • NAID

      120006987697

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones2019

    • Author(s)
      Umeno Tomohiro、Ueda Atsushi、Doi Mitsunobu、Kato Takuma、Oba Makoto、Tanaka Masakazu
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 49 Pages: 151301-151301

    • DOI

      10.1016/j.tetlet.2019.151301

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans via Peptide-Catalyzed Michael Addition Followed by Kishi’s Reductive Cyclization2019

    • Author(s)
      Ueda Atsushi、Tanaka Masakazu、Higuchi Mei、Umeno Tomohiro
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 2 Pages: 989-989

    • DOI

      10.3987/com-18-s(f)63

    • NAID

      120006987689

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Helical Structures of Cyclopentene-based α,α-Disubstituted α-Amino Acid Homopeptides2018

    • Author(s)
      Tanaka Masakazu、Yakabi Haruka、Nakatani Haruki、Ueda Atsushi、Doi Mitsunobu、Oba Makoto
    • Journal Title

      CHIMIA International Journal for Chemistry

      Volume: 72 Issue: 12 Pages: 848-852

    • DOI

      10.2533/chimia.2018.848

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] β-Selective D-Psicofuranosylation of Pyrimidine Bases and Thiols2018

    • Author(s)
      Ueda Atsushi、Nishimura Yuri、Makura Yui、Tanaka Masakazu、Uenishi Jun'ichi
    • Journal Title

      HETEROCYCLES

      Volume: 97 Issue: 2 Pages: 729-729

    • DOI

      10.3987/com-18-s(t)42

    • NAID

      120006987688

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Left-handed helix of three-membered ring amino acid homopeptide interrupted by an N-H...ethereal O type hydrogen bond2018

    • Author(s)
      Y. Koba, A. Ueda, M. Oba, M. Doi, T. Kato, Y. Demizu, M. Tanaka*
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 24 Pages: 7830-7834

    • DOI

      10.1021/acs.orglett.8b03331

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] N末をチオウレアで修飾したヘリカルペプチド触媒による不斉1,4-付加反応2021

    • Author(s)
      佐藤 和樹、梅野 智大、上田 篤志、土井 光暢、加藤 巧馬、田中 正一
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ペプチド側鎖におけるE選択的i,i+4閉環メタセシス反応2021

    • Author(s)
      真倉 唯、上田 篤志、梅野 智大、加藤 巧馬、平山 和浩、土井 光暢、大庭 誠、田中 正一
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] D-プシコフラノースのβ-選択的グリコシル化を利用した(+)-5-チオスクロースの立体選択的合成2021

    • Author(s)
      上田 篤志、真倉 唯、皮 金紅、田中 正一、上西 潤一
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ヘリカルペプチドの側鎖炭素架橋形成反応におけるジ置換アミノ酸とE/Z選択性の関係性2020

    • Author(s)
      真倉 唯、上田 篤志、梅野 智大、加藤 巧馬、平山 和浩、土井 光暢、大庭 誠、田中 正一
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] N末にチオウレア部位を導入したヘリカルペプチド触媒による不斉マイケル付加反応2020

    • Author(s)
      佐藤 和樹、梅野 智大、上田 篤志、土井 光暢、加藤 巧馬、田中 正一
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] アセトナイド保護基を利用したD-タガトフラノースのα選択的グリコシル化反応の開発2020

    • Author(s)
      真倉 唯、上田 篤志、松崎 高志、南野 哲男、田中 正一
    • Organizer
      第30回記念万有福岡シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] ヘリカルペプチドを基盤とした高活性有機分子触媒および不斉配位子としての展開2020

    • Author(s)
      上田 篤志、佐藤 和樹、梅野 智大、田中 正一
    • Organizer
      反応と合成の進歩2020特別企画シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] (+)-5-チオスクロースおよび(+)-5-チオイソスクロースの立体選択的合成2020

    • Author(s)
      真倉 唯、上田 篤志、皮 金紅、田中 正一、上西 潤一
    • Organizer
      第39回日本糖質学会年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] D-プシコフラノースのβ選択的グリコシル化反応の開発2020

    • Author(s)
      上田 篤志、真倉 唯、山下隆則、西村優里、田中 正一、上西 潤一
    • Organizer
      第39回日本糖質学会年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] キラル相間移動触媒を用いるα-トリフルオロメチル化アミノ酸の不斉合成研究2020

    • Author(s)
      上田 篤志、池田 美鈴、大庭 誠、田中 正一
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 五員環状ジ置換アミノ酸を利用したE選択的なペプチド側鎖架橋形成法の開発2020

    • Author(s)
      真倉 唯、上田 篤志、梅野 智大、加藤 巧馬、平山 和浩、土井 光暢、大庭 誠、田中 正一
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] チオウレア部位を導入したヘリカルペプチドによる不斉マイケル付加反応2020

    • Author(s)
      佐藤 和樹、梅野 智大、上田 篤志、田中 正一
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 立体選択的1,3-双極子付加環化反応のためのヘリカルペプチド型ホスフィン配位子の開発2020

    • Author(s)
      梅野 智大、上田 篤志、加藤 巧馬、土井 光暢、田中 正一
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] alpha-Selective glycosidation of D-tagatofuranose using 3,4-O-isopropylidene protection.2019

    • Author(s)
      Yui Makura、Atsushi Ueda、Takashi Matsuzaki、Tetsuo Minamino、Masakazu Tanaka
    • Organizer
      The American Chemical Society Fall 2019 National Meeting & Exposition
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Design of helical peptide foldamers for asymmetric reactions.2019

    • Author(s)
      Tomohiro Umeno、Atsushi Ueda、Takuma Kato、Mitsunobu Doi、Masakazu Tanaka
    • Organizer
      The American Chemical Society Fall 2019 National Meeting & Exposition
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Helical peptide-catalyzed asymmetric Michael addition reactions of malonates to alpha,beta-unsaturated ketones and their synthetic applications.2019

    • Author(s)
      Atsushi Ueda、Mei Higuchi、Tomohiro Umeno、Arisa Sugiyama、Masakazu Tanaka
    • Organizer
      The American Chemical Society Fall 2019 National Meeting & Exposition
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of alpha-trifluoromethyl alpha-amino acids and conformational analysis of their peptides.2019

    • Author(s)
      Misuzu Ikeda, Takuya Kasae, Atsushi Ueda, Makoto Oba, Mitsunobu Doi, Masakazu Tanaka
    • Organizer
      第56回ペプチド討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] Asymmetric Michael addition reaction using peptide-catalysts with a thiourea moiety.2019

    • Author(s)
      Kazuki Sato、Tomohiro Umeno、Atsushi Ueda、Masakazu Tanaka
    • Organizer
      第56回ペプチド討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘリカルペプチドフォルダマーを利用した不斉触媒反応の開発2019

    • Author(s)
      梅野 智大、上田 篤志、加藤 巧馬、土井 光暢、田中 正一
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] ペプチドのN末にチオウレア部位を持つ触媒による不斉1,4-付加反応2019

    • Author(s)
      佐藤 和樹、梅野 智大、上田 篤志、田中 正一
    • Organizer
      第36回日本薬学会九州支部大会
    • Related Report
      2019 Research-status Report
  • [Presentation] 立体選択的 beta-D-プシコフラノシル化およびalpha-D-タガトフラノシル化による希少糖誘導体の合成2019

    • Author(s)
      真倉 唯、上田 篤志、上西 潤一、松崎 高志、南野 哲夫、田中 正一
    • Organizer
      第36回日本薬学会九州支部大会
    • Related Report
      2019 Research-status Report
  • [Presentation] Stereoselective synthesis of alpha-D-tagatofuranosides using acetonide protection.2019

    • Author(s)
      Yui Makura、Atsushi Ueda、Takashi Matsuzaki、Tetsuo Minamino、Masakazu Tanaka
    • Organizer
      Rare Sugar Congress 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Beta-Selective glycosidation of D-psicofuranose.2019

    • Author(s)
      Atsushi Ueda、Yui Makura、Takanori Yamashita、Yuri Nishimura、Masakazu Tanaka、Jun’ichi Uenishi
    • Organizer
      Rare Sugar Congress 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] ケタール保護基を利用したD-プシコフラノースおよびD-タガトフラノースの立体選択的グリコシル化反応2019

    • Author(s)
      真倉 唯、上田 篤志、上西 潤一、松崎 高志、南野 哲男、田中 正一
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ヘリカルペプチド触媒によるマロン酸エステルの不斉マイケル付加反応とその合成的利用2019

    • Author(s)
      上田 篤志、樋口 明、梅野 智大、杉山 綾里紗、田中 正一
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 光学活性α-トリフルオロメチル化ジ置換アミノ酸の合成とそのペプチドの2次構造解析2018

    • Author(s)
      池田 美鈴、笠江 卓矢、上田 篤志、大庭 誠、土井 光暢、田中 正一
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] ピリミジン塩基とチオールのβ選択的D-プシコフラノシル化反応2018

    • Author(s)
      真倉 唯、上田 篤志、西村 優里、上西 潤一、田中 正一
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] Conformational analysis of peptides having 1-aminocyclopentanecarboxylic acids with stapled side chain and their applications to organocatalysts2018

    • Author(s)
      Atsushi Ueda, Mei Higuchi, Suguru Matsumoto, Mitsunobu Doi, Masakazu Tanaka
    • Organizer
      The 256th American Chemical Society National Meeting & Exposition
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] β-Selective D-psicofuranosylation of alcohols, pyrimidine bases, and thiols2018

    • Author(s)
      Atsushi Ueda, Yui Makura, Yuri Nishimura, Masakazu Tanaka, Jun’ichi Uenishi
    • Organizer
      The 256th American Chemical Society National Meeting & Exposition
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] D-プシコフラノースの β 選択的 N-及び S-グリコシル化反応の開発2018

    • Author(s)
      真倉 唯、上田 篤志、西村 優里、田中 正一、上西 潤一
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] (-)-メントン由来のα,α-ジ置換アミノ酸含有ペプチドのX線結晶解析2018

    • Author(s)
      松本 卓、上田 篤志、土井 光暢、田中 正一
    • Organizer
      第62回香料・テルペンおよび精油化学に関する討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Conformational analysis of peptides having α,α-disubstituted α-amino acids and their uses as an organocatalyst2018

    • Author(s)
      Atsushi Ueda, Tomohiro Umeno, Kazuhiro Hirayama, Mei Higuchi, Mitsunobu Doi, Masakazu Tanaka
    • Organizer
      ICPAC Langkawi 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and conformational analysis of peptides having (-)-menthone-derived α, α-disubstituted α-amino acid2018

    • Author(s)
      Suguru Matsumoto, Atsushi Ueda, Mitsunobu Doi, Masakazu Tanaka
    • Organizer
      IKCOC-14
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Stereoselective glycosidation of D-psicofuranose and D-tagatofuranose using ketal protection2018

    • Author(s)
      Yui Makura, Atsushi Ueda, Jun’ichi Uenishi, Takashi Matsuzaki, Tetsuo Minamino, Masakazu Tanaka
    • Organizer
      IKCOC-14
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and analysis of α-trifluoromethylated α-amino acids and thier peptides2018

    • Author(s)
      Atsushi Ueda, Misuzu Ikeda, Takuya Kasae, Makoto Oba, Mitsunobu Doi, Masakazu Tanaka
    • Organizer
      IKCOC-14
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光学活性α-トリフルオロメチル化ジ置換アミノ酸を含有するペプチドの合成と二次構造解析2018

    • Author(s)
      池田 美鈴、笠江 卓矢、上田 篤志、大庭 誠、土井 光暢、田中 正一
    • Organizer
      第35回日本薬学会九州支部大会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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