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Middle-size cyclic peptides containing unnatural amino acids enable the control of higher cell function

Planned Research

Project AreaMiddle molecular strategy: Creation of higher bio-functional molecules by integrated synthesis.
Project/Area Number 15H05837
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionTohoku University

Principal Investigator

DOI TAKAYUKI  東北大学, 薬学研究科, 教授 (90212076)

Co-Investigator(Kenkyū-buntansha) 塚本 裕一  横浜薬科大学, 薬学部, 教授 (70323037)
Project Period (FY) 2015-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥45,500,000 (Direct Cost: ¥35,000,000、Indirect Cost: ¥10,500,000)
Fiscal Year 2019: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2018: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2017: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2016: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2015: ¥10,140,000 (Direct Cost: ¥7,800,000、Indirect Cost: ¥2,340,000)
Keywords中分子 / 環状ペプチド / 非天然型アミノ酸 / フロー合成 / 反応集積化 / 固相合成 / 環化反応 / 不斉合成
Outline of Final Research Achievements

We have developed a method for efficiently synthesizing cyclic peptide natural products and their analogues exhibiting biological activities. Their three-dimensional structures were clarified by X-ray crystal structure analysis and/or a distance geometry method based on NMR studies. We found that it is important to consider the membrane permeability of the cyclic peptides. Generally, cyclic peptides have a large polar surface area and low membrane permeability. In cyclic peptides that exhibit biological activity, however, the polar surface area decreases due to the intramolecular hydrogen bond between the amide bonds, resulting in sufficient membrane permeability. In addition, we have developed an asymmetric aldol reaction and Mannich reaction utilizing a flow system and have realized reaction integration that can efficiently supply starting materials required for the synthesis of middle-size molecules.

Academic Significance and Societal Importance of the Research Achievements

ガン細胞の増殖を抑制する活性、骨を溶かす破骨細胞を抑制する活性を有するなど、天然から発見された創薬シーズである環状ペプチド化合物は、従来の低分子量の化合物とは異なり中分子量(500から2,000程度)であり、難解な構造をもつ。我々はこれら中分子環状ペプチド化合物とその周辺化合物を効率良く合成する手法を確立し、活性評価、三次元構造解析を行って、その有用性、および活性発現に必要な構造情報を明らかにした。この際、フロー合成法により、合成の出発物質を効率良く供給できる反応集積化を実現した。

Report

(6 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (61 results)

All 2020 2019 2018 2017 2016 2015 Other

All Int'l Joint Research (5 results) Journal Article (19 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 19 results,  Open Access: 6 results,  Acknowledgement Compliant: 1 results) Presentation (28 results) (of which Int'l Joint Research: 7 results,  Invited: 6 results) Remarks (9 results)

  • [Int'l Joint Research] イーストアングリア大学(英国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Univ East Anglia(英国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Univ East Anglia(英国)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] University of East Anglia(英国)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] University of East Anglia(英国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Structure–Activity Relationship Study on Col-003, a Protein–Protein Interaction Inhibitor between Collagen and Hsp472020

    • Author(s)
      Yoshida Masahito、Saito Masazumi、Ito Shinya、Ogawa Koji、Goshima Naoki、Nagata Kazuhiro、Doi Takayuki
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 68 Issue: 3 Pages: 220-226

    • DOI

      10.1248/cpb.c19-00634

    • NAID

      130007804070

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2020-03-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Biphenylalanine Analogue of Apratoxin A Displaying Substantially Enhanced Cytotoxicity2020

    • Author(s)
      Doi Takayuki、Onda Yuichi、Fukushi Kazuki、Ohsawa Kosuke、Yoshida Masahito、Masuda Yuichi
    • Journal Title

      HETEROCYCLES

      Volume: 101 Issue: 2 Pages: 679-691

    • DOI

      10.3987/com-19-s(f)35

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of Protected l-allo-Enduracididine and l-Enduracididine via Asymmetric Nitroaldol Reaction2020

    • Author(s)
      Ohsawa Kosuke、Zhao Hongbin、Tokunaga Takuya、Thomas Carys、Ganesan A.、Masuda Yuichi、Doi Takayuki
    • Journal Title

      Synthesis

      Volume: 52 Issue: 06 Pages: 942-948

    • DOI

      10.1055/s-0039-1691522

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Scalable Total Syntheses and Structure‐Activity Relationships of Haouamine A, B, and their Derivatives as Stable Formate Salts2020

    • Author(s)
      Hirokazu Tsukamoto, Saki Nakamura, Akito Tomida, Takayuki Doi
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 55 Pages: 12528-12532

    • DOI

      10.1002/chem.202001756

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Structural Revision of Cyclotetrapeptide Asperterrestide A2019

    • Author(s)
      Ohsawa Kosuke、Sugai Masato、Zhang Linnan、Masuda Yuichi、Yoshida Masahito、Doi Takayuki
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 11 Pages: 6765-6779

    • DOI

      10.1021/acs.joc.9b00526

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium‐Catalyzed Umpolung Type‐II Cyclization of Allylic Carbonate‐Aldehydes Leading to 3‐Methylenecycloalkanol Derivatives2019

    • Author(s)
      Tsukamoto Hirokazu、Kawase Ayumu、Doi Takayuki
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 361 Issue: 16 Pages: 3733-3738

    • DOI

      10.1002/adsc.201900450

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] First Total Synthesis of Palmarumycin C6 based on Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene to 3-Bromo-1-indenone2019

    • Author(s)
      Doi Takayuki、Tsukamoto Hirokazu、Nomura Yumi
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 1 Pages: 549-565

    • DOI

      10.3987/com-18-s(f)52

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates2019

    • Author(s)
      Tsukamoto Hirokazu、Kawase Ayumu、Omura Hirotaka、Doi Takayuki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 92 Issue: 10 Pages: 1743-1753

    • DOI

      10.1246/bcsj.20190167

    • NAID

      130007728663

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium(0)-Lithium Iodide Cocatalyzed Asymmetric Hydroalkylation of Conjugated Enynes with Pronucleophiles Leading to 1,3-Disubstituted Allenes2019

    • Author(s)
      Hirokazu Tsukamoto, Tatsuya Konno, Kazuya Ito, and Takayuki Doi
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 17 Pages: 6811-6814

    • DOI

      10.1021/acs.orglett.9b02439

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium(0)-catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-methylene-2H-1-benzopyran-4-ols2019

    • Author(s)
      Kawase Ayumu、Omura Hirotaka、Doi Takayuki、Tsukamoto Hirokazu
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 11 Pages: 1402-1405

    • DOI

      10.1246/cl.190642

    • NAID

      130007741835

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclodepsipeptide Natural Products Apratoxins A and C and Their Analogs2018

    • Author(s)
      T. Doi, Y. Masuda, M. Yoshida
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 11 Pages: 1170-1175

    • DOI

      10.5059/yukigoseikyokaishi.76.1170

    • NAID

      130007503326

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2018-11-01
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of Spiromamakone A and Structure Revision of Spiropreussione A2018

    • Author(s)
      H. Tsukamoto, S.Hanada, Y. Nomura, T. Doi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 86 Issue: 16 Pages: 9430-9441

    • DOI

      10.1021/acs.joc.8b01075

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] onjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application To Synthesize the Proposed Structure of Spiropreussione A2018

    • Author(s)
      H. Tsukamoto, Y. Nomura, K. Fujiwara, S. Hanada, T. Doi
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 10 Pages: 3140-3143

    • DOI

      10.1021/acs.orglett.8b01259

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A total synthesis and biological evaluation of siladenoserinol A and its analogues2018

    • Author(s)
      M. Yoshida, K. Saito, H. Kato, S. Tsukamoto, T. Doi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 印刷中 Issue: 18 Pages: 5147-5150

    • DOI

      10.1002/anie.201801659

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Systematic Analysis of the Relationship among 3D Structure, Bioactivity, and Membrane Permeability of PF1171F, a Cyclic Hexapeptide with Paralyzing Effects on Silkworms2017

    • Author(s)
      Masuda Yuichi、Tanaka Ren、Ganesan A.、Doi Takayuki
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 21 Pages: 11447-11463

    • DOI

      10.1021/acs.joc.7b01975

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Stereoselective Synthesis of beta-Amino Acid Derivatives by Asymmetric Mannich Reaction in Flow2017

    • Author(s)
      M. Yoshida, K. Umeda, T. Doi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 10 Pages: 1157-1163

    • DOI

      10.1246/bcsj.20170194

    • NAID

      130006770674

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Conformation-Based Design and Synthesis of Apratoxin A Mimetics Modified at the α,β-Unsaturated Thiazoline Moiety2017

    • Author(s)
      Onda Yuichi、Masuda Yuichi、Yoshida Masahito、Doi Takayuki
    • Journal Title

      J. Med. Chem.

      Volume: 60 Issue: 15 Pages: 6751-6765

    • DOI

      10.1021/acs.jmedchem.7b00833

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Selective inhibition of sterolO-acyltransferase 1 isozyme by beauveriolide III in intact cells2017

    • Author(s)
      T. Ohshiro, K. Kobayashi, M. Ohba, D. Matsuda, L. L. Rudel, T. Takahashi, T. Doi, H. Tomoda
    • Journal Title

      Scientific Reports

      Volume: 7 Issue: 1 Pages: 4163-4163

    • DOI

      10.1038/s41598-017-04177-8

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Combinatorial Solid-Phase Synthesis and Biological Evaluation of Cyclodepsipeptide Destruxin B as a Negative Regulator for Osteoclast Morphology2016

    • Author(s)
      H. Sato, M. Yoshida, H. Murase, H. Nakagawa, T. Doi
    • Journal Title

      ACS Combinatorial Science

      Volume: 18 Issue: 9 Pages: 590-595

    • DOI

      10.1021/acscombsci.6b00076

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 構造活性相関研究を指向した生物活性新奇鎖状ペプチドJBIR-126の全合成2019

    • Author(s)
      大山皓介、吉田将人、新家一男、土井隆行
    • Organizer
      第115回有機合成シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Biological Evaluation of 3D Structure-Mimicked Apratoxin A Analogues2019

    • Author(s)
      Takayuki Doi, Kazuki Fukushi, Yuichi Onda, Masahito Yoshida
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 環状テトラペプチドAsperterrestide A の全合成および構造訂正2019

    • Author(s)
      大澤宏祐 、菅井柾人、張林楠、増田裕一、吉田将人、土井隆行
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 生物活性をもつ中分子環状ペプチドの合成と三次元構造解析2019

    • Author(s)
      土井隆行
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Synthetic study for novel Foxo3a inhibitor JBIR-1412019

    • Author(s)
      Kotaro Yasoshima, Masahito Yoshida, Teppei Kawahara, Kazuo Shin-ya, and Takayuki Doi
    • Organizer
      The 56th Japanese Peptide Symposium
    • Related Report
      2019 Annual Research Report
  • [Presentation] 0価パラジウム触媒を用いた共役エンインのヒドロアルキル化反応による光学活性アレン合成法の開発2019

    • Author(s)
      伊藤和也,金野達也,土井隆行,塚本裕一
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 光学活性なシクロヘキセノンのβ脱離を利用したhaouamine類の全合成研究2019

    • Author(s)
      塚本裕一、富田昂仁、中村早希、土井隆行
    • Organizer
      第116回有機合成シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 三次元構造を模倣したapratoxin A誘導体の合成と生物活性評価2019

    • Author(s)
      土井隆行,福士和希,恩田勇一,吉田将人
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 中分子環状ペプチドの合成、生物活性、三次元構造2019

    • Author(s)
      土井隆行
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Synthesis, 3D Structure Analysis, and Biological Evaluation of Apratoxin A and Its Analogues2018

    • Author(s)
      Takayuki Doi
    • Organizer
      10th International Peptide Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光学活性アジリジンに対する連続アルキル化反応を鍵としたカルノサジン類の効率的合成法の開発2018

    • Author(s)
      大澤宏祐,窪田準也,土井隆行
    • Organizer
      第114回有機合成シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 新規抗菌活性を有するTeixobactin の合成研究2018

    • Author(s)
      大澤 宏祐, 徳永 拓野, Thomas Carys, A. Ganesan, 増田 裕一, 土井隆行
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 抗腫瘍活性を有するAsperterrestide A の合成研究2018

    • Author(s)
      大澤 宏祐, 菅井 柾人, 張 林楠, 増田 裕一, 吉田将人, 土井 隆行
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] デストラキシンB ラクタム誘導体の全合成と生物活性評価2018

    • Author(s)
      吉田 将人, 今野 源, 丹羽 悠菜, 中川 大, 土井隆行
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Piperidamycin F誘導体の合成研究2017

    • Author(s)
      吉田将人,高橋優輔,関岡直樹,新家一男,土井隆行
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内キャンパス,仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] Teixobactinの合成研究2017

    • Author(s)
      大澤宏祐,徳永拓野,増田裕一,土井隆行
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内キャンパス,仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthetic study for teixobactin2017

    • Author(s)
      K. Ohsawa, T. Tokunaga, C. Thomas, A. Ganesan, Y. Masuda, T. Doi
    • Organizer
      The 54rd Japanese Peptide Symposium
    • Related Report
      2017 Annual Research Report
  • [Presentation] スピロママコンAおよび類縁体の合成研究2017

    • Author(s)
      塚本裕一,花田祥吾,熊坂幸一,土井隆行
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Spiropreussione A提唱構造の全合成2017

    • Author(s)
      塚本裕一,野村友美,藤原広一,土井隆行
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Teixobactinの合成研究2017

    • Author(s)
      大澤宏祐,徳永拓野,Carys Thomas, A. Ganesan, 増田裕一,土井隆行
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 創薬展開を指向した中分子環状ペプチドdestruxin 類の合成を基盤とする機能評価と高活性分子プローブの創製2017

    • Author(s)
      吉田将人,佐藤寛,安達謙太, 今野源, 石田恵崇,村瀬隼人,丹羽悠菜,中川大,土井隆行
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 3D structure-based design and synthesis of apratoxin A mimetics2017

    • Author(s)
      Y. Onda, Y. Masusa, M. Yoshida, T. Doi
    • Organizer
      12th Australian Peptide Conference 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Biological Evaluation of Cyclodepsipeptide Natural Products2016

    • Author(s)
      Takayuki Doi
    • Organizer
      The 10th International Symposium on Integrated Synthesis (ISONIS-10)
    • Place of Presentation
      Awaji Yumebutai International Conference Center, Hyogo
    • Year and Date
      2016-11-17
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Protein-Protein Interaction Inhibitor Thielocin B12016

    • Author(s)
      T. Doi, M. Yoshida, K. Ohsawa, K. Shin-ya, M. Takagi, Y. Uekusa, T. Yamaguchi, K.i Kato, T. Hirokawa, T. Natsume
    • Organizer
      Symposium on Foldamers 2016
    • Place of Presentation
      IECB, Bordeaux-Pessac, France
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 環状デプシペプチド天然物の全合成と生物活性評価2016

    • Author(s)
      土井隆行
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Biologically Active Cyclodepsipeptide Natural Product2016

    • Author(s)
      Takayuki Doi
    • Organizer
      The 12th International Symposium on Organic Reactions (ISOR-12)
    • Place of Presentation
      Kyoto Terrsa, Kyoto
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total synthesis of cyclodepsipeptide natural products and their biological evaluation2015

    • Author(s)
      T. Doi
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] カイコ麻痺活性を示す環状ペプチドPF1171類の全合成と三次元構造ー活性相関2015

    • Author(s)
      増田裕一,田中錬,土井隆行
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Remarks] 東北大学薬学研究科反応制御化学分野学会発表

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/presentation.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] Doi Laboratory Presentations

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/presentation-e.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 東北大学薬学研究科反応制御化学分野論文リスト

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/publication.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] Doi Laboratory Publications

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/publication-e.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 東北大学薬学部,大学院薬学研究科 反応制御化学分野 Doi Laboratory 論文発表

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/publication.html

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report 2016 Annual Research Report 2015 Annual Research Report
  • [Remarks] 東北大学薬学部,大学院薬学研究科 反応制御化学分野 Doi Laboratory 学会発表

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/presentation.html

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report 2016 Annual Research Report 2015 Annual Research Report
  • [Remarks] Doi Laboratory, Publication List

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/publication-e.html

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report 2015 Annual Research Report
  • [Remarks] Doi Laboratory, Presentations in Symposium

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/presentation-e.html

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report 2016 Annual Research Report 2015 Annual Research Report
  • [Remarks] Doi Laboratory, Publication List Japanese

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/publication-e.html

    • Related Report
      2016 Annual Research Report

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Published: 2015-07-02   Modified: 2022-11-04  

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