Updated on 2024/12/05

写真a

 
FUSE Shinichiro
 
Organization
Graduate School of Pharmaceutical Sciences Department of Basic Medicinal Sciences Organic Chemistry Professor
Graduate School
Graduate School of Pharmaceutical Sciences
Undergraduate School
School of Engineering Materials Science and Engineering
Title
Professor
External link

Degree 1

  1. Doctor (Engineering) ( 2005.3   Tokyo Institute of Technology ) 

Research Interests 4

  1. Micro-Flow Synthesis

  2. Synthetic Organic Chemistry

  3. Automated Synthesis

  4. 天然物合成

Research Areas 2

  1. Nanotechnology/Materials / Synthetic organic chemistry  / Synthetic Organic Chemistry

  2. Life Science / Pharmaceutical chemistry and drug development sciences  / Process Chemistry

Research History 5

  1. Tokyo Institute of Technology   Laboratory for Chemistry and Life Science, Institute of Innovative Research   Associate professor

    2016.4 - 2019.10

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    Country:Japan

  2. Tokyo Institute of Technology   Chemical Resources Laboratory   Associate professor

    2015.2 - 2016.3

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    Country:Japan

  3. Tokyo Institute of Technology   Department of Applied Chemistry, Graduate School of Science and Engineering   Associate Professor

    2008.3 - 2015.1

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    Country:Japan

  4. Harvard University   Department of Chemistry and Chemical Biology   Postdoctoral Fellow

    2006.5 - 2008.2

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    Country:United States

  5. ChemGenesis Inc.   Development Department   Researcher

    2005.4 - 2006.4

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    Country:Japan

Education 1

  1. Tokyo Institute of Technology   Graduate School, Division of Science and Engineering   Department of Applied Chemistry

    2000.4 - 2005.3

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    Country: Japan

Professional Memberships 10

  1. 天然物化学談話会   世話人代表

    2022.7 - 2024.7

  2. 天然物化学談話会   世話人

    2011.7 - 2024.7

  3. The Chemical Society of Japan

  4. Japanese Society for Chemical Biology

  5. Kinka Chemical Society

  6. The Pharmaceutical Society of Japan

  7. 有機合成化学協会

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  8. アメリカ化学会

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  9. The Japanese Peptide Society

  10. 日本プロセス化学会

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Awards 8

  1. The Award of Ohsumi Life Science Research Society for Young Scientist

    2021.11   Ohsumi Life Science Research Society   Development of Micro-Flow Synthetic Approaches for Accelerating Peptide Science

    Shinichiro Fuse

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    Award type:Award from Japanese society, conference, symposium, etc.  Country:Japan

  2. Lectureship Award

    2017.11   Asian Core Program/Advance Research Network   Highly efficient amide bond formation using micro-flow technology

    Shinichiro Fuse

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    Award type:Award from international society, conference, symposium, etc. 

  3. 東工大挑戦的研究賞 学長特別賞

    2017.7   東京工業大学   大量核酸供給を可能にする革新的マイクロフロー合成法開発への挑戦

    布施新一郎

  4. 第35回有機合成化学奨励賞

    2016.12   有機合成化学協会   サイト選択的反応の開発と多官能基性化合物合成への展開

    布施新一郎

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    Award type:Award from Japanese society, conference, symposium, etc. 

  5. 日本化学会第95春季年会「若い世代の特別講演会」講演者

    2015.3   日本化学会   マイクロフロー合成法を駆使する高選択的反応を基軸とした天然物合成

    布施新一郎

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    Award type:Award from Japanese society, conference, symposium, etc. 

  6. 東京工業大学工系若手奨励賞

    2010.8   東京工業大学工系   マイクロリアクターを活用する活性型ビタミンD3の高選択的合成法の確立

    布施新一郎

  7. 有機合成化学協会日産化学工業研究企画賞

    2008.12   有機合成化学協会   マイクロリアクターを活用した反応系内生成ホスゲンによる高速かつ高選択的反応の開発

    布施新一郎

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    Award type:Award from Japanese society, conference, symposium, etc. 

  8. 第40回天然物化学談話会奨励賞

    2005.7   天然物化学談話会   ラボオートメーションの導入による有機合成の効率化を指向したタキソールの全合成研究

    布施新一郎

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    Award type:Award from Japanese society, conference, symposium, etc. 

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Papers 67

  1. Switching between P-acylation and O-acylation of H-phosphonates with chloroformates by changing acyl pyridinium and acyl ammonium ions in a microflow reactor Reviewed

    Chemical Communications   Vol. 60   page: 10874 - 10877   2024.8

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/D4CC02871F

  2. フロー・自動合成,機械学習技術が駆動する有機合成の革新 Invited

    布施 新一郎

    日本農薬学会誌   Vol. 49 ( 2 ) page: 99 - 105   2024.8

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:公益社団法人 有機合成化学協会  

  3. One-step syntheses of diaza-dioxa-fenestranes via the sequential (3+2) cycloadditions of linear precursors and their structural analyses Reviewed

    Nature Communications   Vol. 15   page: 6087   2024.7

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41467-024-49935-1

  4. ペプチドの次世代フロー・マイクロ合成法 Invited

    布施 新一郎

    月刊ファインケミカル   Vol. 53 ( 7 ) page: 15 - 21   2024.7

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:公益社団法人 有機合成化学協会  

  5. Rapid and mild nucleophilic substitution of highly active (indol-2-yl)methyl electrophile in a microflow reactor Invited Reviewed

    Synthesis   Vol. 56 ( 17 ) page: 2663 - 2669   2024.6

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0043-1775370

  6. Effect of Brønsted acids on the activation of mixed anhydride/mixed carbonic anhydride and C-terminal-free N-methylated peptide synthesis in a micro-flow reactor, Reviewed

    Chemistry a European Journal   Vol. 30 ( 38 ) page: e202401402   2024.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.202401402

  7. Rapid in situ generation of 2-(halomethyl)-5-phenylfuran and nucleophilic addition in a microflow reactor Reviewed

    Y. Matsuura, S. Fuse

    Organic and Biomolecular Chemistry   Vol. 22 ( 17 ) page: 3448 - 3452   2024.4

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Journal of Organic Chemistry  

    Unsymmetrical H-phosphonates were synthesized by a rapid (<15 s) and mild (20 °C) process in a microflow reactor as the first example of the sequential direct substitution of the chlorine atoms in PCl3 with alkoxyl/aryloxy groups using equivalent amounts of PCl3 and alcohols. The optimal base concentration differed in each step, presumably attributed to differences in the Brønsted basicity of the electrophilic intermediates. Phosphite hydrolysis was observed, and the structure-hydrolysis relationship was quantitatively evaluated.

    DOI: 10.1039/D4OB00358F

  8. Facile generation of t-butoxycarbonyl chloride equivalent and its use in micro-flow reactor Invited Reviewed

    K. Miyamoto, R. Okabe, S. Fuse

    Organic Process Research and Development   Vol. 28 ( 5 ) page: 1971 - 1978   2024.4

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Journal of Organic Chemistry  

    Unsymmetrical H-phosphonates were synthesized by a rapid (<15 s) and mild (20 °C) process in a microflow reactor as the first example of the sequential direct substitution of the chlorine atoms in PCl3 with alkoxyl/aryloxy groups using equivalent amounts of PCl3 and alcohols. The optimal base concentration differed in each step, presumably attributed to differences in the Brønsted basicity of the electrophilic intermediates. Phosphite hydrolysis was observed, and the structure-hydrolysis relationship was quantitatively evaluated.

    DOI: 10.1021/acs.oprd.4c00009

  9. Microflow, sequential coupling and cyclization approach for synthesis of cyclic phosphotriesters from PCl3 Reviewed

    K. Nakabayashi, H. Kitamura, S. Fuse

    CHEMISTRY-AN ASIAN JOURNAL   Vol. 19 ( 11 ) page: e202400256   2024.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemistry - An Asian Journal  

    Substituted indoles are important as drugs. A number of valuable indoles have been synthesized via nucleophilic substitution at the 3’-position of indoles. However, the preparation of an indolylmethyl electrophile containing a tertiary carbon at the 3’-position and its subsequent nucleophilic substitution are challenging owing to the instability of the electrophile. Herein, we demonstrated the rapid one-flow synthesis of indoles via sequential 1,2-addition/nucleophilic substitution of indolyl-3-carbaldehydes. The use of a microflow technology helped in suppressing the undesired reactions caused by the unstable intermediates, resulting in significantly higher yields and reproducibility compared to those under batch conditions. A crown ether was effective when 1-alkylindole-3-carboxaldehyde was used as a substrate. However, the crown ether exerted a detrimental effect when 1H-indole-3-carboxaldehyde was used. A total of 15 structurally diverse indole derivatives were obtained in generally acceptable to good yields.

    DOI: 10.1002/asia.202400256

  10. Micro-flow heteroatom alkylation <i>via</i> TfOH-mediated rapid <i>in situ</i> generation of carbocations and subsequent nucleophile addition Reviewed

    Matsuura, Y; Fuse, S

    CHEMICAL COMMUNICATIONS   Vol. 60   page: 2497 - 2500   2024.1

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Communications  

    A rapid nucleophilic substitution reaction was developed using carbocations generated from diarylmethanol and trifluoromethanesulfonic acid. Undesired reactions caused by the carbocations were suppressed, presumably due to the rapid and uniform generation of carbocations and the subsequent rapid and uniform distribution of nucleophiles by the micro-flow technology.

    DOI: 10.1039/d3cc06308a

    Web of Science

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  11. Microflow Synthesis of Unsymmetrical H-Phosphonates via Sequential and Direct Substitution of Chlorine Atoms in Phosphorus Trichloride with Alkoxy Groups. Reviewed

    Tanaka Y, Kitamura H, Fuse S

    The Journal of organic chemistry     2024.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Journal of Organic Chemistry  

    Unsymmetrical H-phosphonates were synthesized by a rapid (<15 s) and mild (20 °C) process in a microflow reactor as the first example of the sequential direct substitution of the chlorine atoms in PCl3 with alkoxyl/aryloxy groups using equivalent amounts of PCl3 and alcohols. The optimal base concentration differed in each step, presumably attributed to differences in the Brønsted basicity of the electrophilic intermediates. Phosphite hydrolysis was observed, and the structure-hydrolysis relationship was quantitatively evaluated.

    DOI: 10.1021/acs.joc.3c02467

    Scopus

    PubMed

  12. Multi-objective Bayesian optimisation using <i>q</i>-noisy expected hypervolume improvement (<i>q</i>NEHVI) for the Schotten-Baumann reaction Reviewed International coauthorship

    Zhang, JYZ; Sugisawa, N; Felton, KC; Fuse, S; Lapkin, AA

    REACTION CHEMISTRY & ENGINEERING   Vol. 9 ( 3 ) page: 706 - 712   2023.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Reaction Chemistry and Engineering  

    Amide bond formation is one of the most prevalent reactions in the pharmaceutical industry, among which the Schotten-Baumann reaction with a long history is useful as a potential green amide formation approach. However, the use of water in the reaction system often causes undesired hydrolysis and can generate a multiphase system. This makes the reaction space complex, making it challenging to find the optimal conditions. In this study, the Schotten-Baumann reaction was studied in a continuous flow and was optimised with two objectives using a Bayesian optimisation algorithm based on the q-noisy expected hypervolume improvement (qNEHVI) acquisition function. The algorithm guided the experiment design over a range of electrophiles, equivalents, solvents, and flow rates, and was able to identify the Pareto front of optimal solutions efficiently. Based on the optimisation results, reactions under a flow and batch conditions were compared; undesired hydrolysis was suppressed successfully using the flow conditions. Finally, the relationship between the solvent and flow rate was discussed to gain more insights into this reaction.

    DOI: 10.1039/d3re00502j

    Web of Science

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  13. One-Flow Synthesis of Substituted Indoles via Sequential 1,2-Addition/Nucleophilic Substitution of Indolyl-3-Carbaldehydes Reviewed

    Fuse, S; Kanda, S; Masui, H

    CHEMISTRY-AN ASIAN JOURNAL   Vol. 19 ( 1 ) page: e202300909   2023.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemistry - An Asian Journal  

    Substituted indoles are important as drugs. A number of valuable indoles have been synthesized via nucleophilic substitution at the 3’-position of indoles. However, the preparation of an indolylmethyl electrophile containing a tertiary carbon at the 3’-position and its subsequent nucleophilic substitution are challenging owing to the instability of the electrophile. Herein, we demonstrated the rapid one-flow synthesis of indoles via sequential 1,2-addition/nucleophilic substitution of indolyl-3-carbaldehydes. The use of a microflow technology helped in suppressing the undesired reactions caused by the unstable intermediates, resulting in significantly higher yields and reproducibility compared to those under batch conditions. A crown ether was effective when 1-alkylindole-3-carboxaldehyde was used as a substrate. However, the crown ether exerted a detrimental effect when 1H-indole-3-carboxaldehyde was used. A total of 15 structurally diverse indole derivatives were obtained in generally acceptable to good yields.

    DOI: 10.1002/asia.202300909

    Web of Science

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  14. Switchable Synthesis of 7-and 14-Membered Cyclic Peptides Containing N-Methyl- and & beta;-Amino Acids Utilizing Microflow Technology Reviewed

    Fuse Shinichiro, Okabe Ren

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   Vol. 26 ( 35 ) page: e202300700   2023.8

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    Publisher:European Journal of Organic Chemistry  

    Smaller cyclic peptides containing non-proteinogenic amino acids have garnered much attention for use as drugs, but their chemical synthesis is extremely challenging. In this study, a rapid (60.5 min) synthesis of 7- and 14-membered cyclic peptides containing N-methyl- and β-amino acids was achieved by only switching the concentrations (0.20 M or 0.01 M) of the substrates. The developed approach required neither expensive transition-metals nor expensive coupling agents. As far as we could ascertain, this is the first report of the synthesis of smaller (≤16-membered) cyclic N-methylated peptides via dimerization-cyclization strategy.

    DOI: 10.1002/ejoc.202300700

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  15. Rapid and column-chromatography-free peptide chain elongation via a one-flow, three-component coupling approach Reviewed

    Sugisawa Naoto, Ando Akira, Fuse Shinichiro

    Chemical Science   Vol. 14 ( 25 ) page: 6986 - 6991   2023.6

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/d3sc01333b

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  16. One-Flow Syntheses of Unsymmetrical Sulfamides and <i>N</i>-Substituted Sulfamate Esters Invited Reviewed

    Sugisawa Naoto, Nakabayashi Kohei, Sugisawa Hiroki, Fuse Shinichiro

    ORGANIC LETTERS   Vol. 26 ( 14 ) page: 2739 - 2744   2023.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Organic Letters  

    We developed one-flow syntheses of unsymmetrical sulfamides and N-substituted sulfamate esters by changing a nucleophile and a tertiary amine from inexpensive and commercially available chlorosulfonic acid. In the synthesis of N-substituted sulfamate esters, unexpected symmetrical sulfite formation was suppressed by changing the tertiary amine. The effect of tertiary amines was proposed using linear regression. Our approach rapidly (≤90 s) provides desired products containing acidic and/or basic labile groups without tedious purification under mild (20 °C) conditions.

    DOI: 10.1021/acs.orglett.3c01546

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  17. Continuous-/Micro-Flow Reactions Using Highly Electrophilic PCl3 and POCl3. Invited Reviewed

    Kitamura H, Fuse S

    ChemPlusChem   Vol. 88 ( 6 ) page: e202300176   2023.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cplu.202300176

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  18. Peptide Cyclization by the Use of Acylammonium Species Reviewed

    Shamoto Otoka, Komuro Keiji, Sugisawa Naoto, Chen Ting-Ho, Nakamura Hiroyuki, Fuse Shinichiro

    Angewandte Chemie International Edition   Vol. 62 ( 27 ) page: e202300647   2023.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Angewandte Chemie - International Edition  

    Although cyclic peptides have become increasingly important as drugs, the most conventional peptide cyclization method using moderately active coupling agents suffers from a lot of waste and high cost as well as long reaction times and burdensome purification. Herein, we report an unconventional approach to peptide cyclization that uses acylammonium species generated from inexpensive and less wasteful Me2NBn and ClCO2i-Pr. Using this approach, we observed the desired rapid activation of the C-terminus of cyclization precursors by an acylammonium ion for rapid and epimerization/dimerization-free cyclization of synthetically challenging peptides, including a difficult cyclization involving N-methyl amide bond formation. The ease of purification, productivities, and reaction mass efficiencies of our approach were significantly superior to those in previous reports. We synthesized a previously reported versicotide D analogue, and our data indicated that its assigned stereostructure should be revised.

    DOI: 10.1002/anie.202300647

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  19. Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution Reviewed

    Hisashi Masui, Sena Kanda, Shinichiro Fuse

    Communications Chemistry   Vol. 6   page: 47   2023.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s42004-023-00837-1

  20. A liquid-phase continuous-flow peptide synthesizer for preparing C-terminal free peptides Reviewed

    Yuma Otake, Kyohei Adachi, Yoshiaki Yamashita, Natsumi Iwanaga, Hirokatsu Sunakawa, Taiki Shamoto, Jun-ichi Ogawa, Atsushi Ito, Yutaka Kobayashi, Keiichi Masuya, Shinichiro Fuse, Daisuke Kubo, Hidenosuke Itoh

    Reaction Chemistry & Engineering   Vol. 8 ( 4 ) page: 863 - 870   2022.12

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/D2RE00453D

  21. Micro-flow N-acylation using highly electrophilic acyl ammonium cations for peptide and urethane-protected N-carboxyanhydride syntheses Invited Reviewed

    Hisashi Masui, Shinichiro Fuse

    Journal of Synthetic Organic Chemistry, Japan   Vol. 80 ( 11 ) page: 986 - 993   2022.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.5059/yukigoseikyokaishi.80.986

  22. Sequential Nucleophilic Substitution of Phosphorus Trichloride with Alcohols in a Continuous-Flow Reactor and Consideration of a Mechanism for Reduced Over-reaction through the Addition of Imidazole Reviewed

    Hiroshi Kitamura, Yuma Otake, Naoto Sugisawa, Hiroki Sugisawa, Tomonori Ida, Hiroyuki Nakamura, Shinichiro Fuse

    CHEMISTRY-A EUROPEAN JOURNAL   Vol. 28 ( 37 ) page: e202200932   2022.7

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.202200932

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  23. Recent Advances in the Solid- and Solution-Phase Synthesis of Peptides and Proteins Using Microflow Technology Invited Reviewed

    Masui Hisashi, Fuse Shinichiro

    ORGANIC PROCESS RESEARCH & DEVELOPMENT   Vol. 26 ( 6 ) page: 1751 - 1765   2022.6

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    Authorship:Last author, Corresponding author   Language:Japanese   Publisher:Organic Process Research and Development  

    Peptides have become increasingly important as drugs and drug candidates. In particular, specialty peptides have garnered considerable attention in recent years because of their improved metabolic stability, higher affinity, and biological target selectivity; some of them have the ability to enable cell membrane permeation and oral administration. Despite its long history, peptide synthesis has various limitations, such as high cost, generation of large amounts of waste, and the requirement for hazardous reagents and solvents. Microflow synthesis, wherein the inner diameter of the reaction tube is ≤1 mm, presents several advantages compared with conventional batch synthesis, such as precise control of the reaction time on a short scale, precise reaction temperature control, and facile scale-up with high reproducibility. Microflow technology has been utilized for peptide synthesis since the beginning of the 21st century. The advantages of microflow synthesis enable the use of highly active and unstable chemical species or high-Temperature conditions that accelerate peptide synthesis. The combined use of microflow technology, automated synthesis, and online monitoring technologies has emerged in recent years. This approach not only improved the synthetic efficiency but also afforded large amounts of reliable data that can be used to train machine learning models. This review summarizes the solid-and solution-phase syntheses of α-peptides and specialty peptides, including N-methylated peptides, β-peptides, and cyclic peptides, reported mainly after 2017. The recently reported mesoflow peptide syntheses (inner diameter of the reaction channels > 1 mm), the microflow automated syntheses, and in-line analysis are covered in this review.

    DOI: 10.1021/acs.oprd.2c00074

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  24. A micro-flow rapid dual activation approach for urethane-protected alpha-amino acid N-carboxyanhydride synthesis Reviewed

    Okabe Ren, Sugisawa Naoto, Fuse Shinichiro

    ORGANIC & BIOMOLECULAR CHEMISTRY   Vol. 20 ( 16 ) page: 3303 - 3310   2022.3

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    Authorship:Last author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/d2ob00167e

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  25. Continuous-Flow Synthesis of N-Methylated Peptides via Generation of an Acyl N-Methylimidazolium Cation.

    Masui H, Fuse S

    Chemical Protein Synthesis   Vol. 2530   page: 45 - 53   2022

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    Language:English   Publisher:Methods in Molecular Biology  

    A detailed protocol is described for the continuous-flow synthesis of N-methylated peptides. N-Methylated peptides are very important class of bioactive compounds compared with normal peptides because they can enhance oral bioavailability, cell membrane permeability, and stability against enzymatic degradation. In our developed flow synthesis, a variety of N-methylated dipeptides is obtained in high yields without severe racemization from equivalent amounts of amino acids. The addition of a strong Brønsted acid is critical to generate the highly reactive N-methylimidazolium cation species to accelerate the amidation. The developed approach enabled the synthesis of a bulky peptide with a higher yield in a shorter amount of time compared with the results of conventional amidation.

    DOI: 10.1007/978-1-0716-2489-0_4

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  26. Rapid and mild one-flow synthetic approach to unsymmetrical sulfamides guided by Bayesian optimization Reviewed International coauthorship

    Naoto Sugisawa, Hiroki Sugisawa, Yuma Otake, Roman V. Krems, Hiroyuki Nakamura, Shinichiro Fuse

    Chemistry -Methods   Vol. 1 ( 11 ) page: 484 - 490   2021.8

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cmtd.202100053

  27. I Love Synthetic Organic Chemistry!

    Fuse Shinichiro

    Journal of Synthetic Organic Chemistry, Japan   Vol. 79 ( 4 ) page: 346 - 348   2021.4

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    Language:Japanese   Publisher:The Society of Synthetic Organic Chemistry, Japan  

    DOI: 10.5059/yukigoseikyokaishi.79.346

    CiNii Research

  28. Rapid and mild lactamization using highly electrophilic triphosgene in a micro-flow reactor, Reviewed

    Shinichiro Fuse, Keiji Komuro, Yuma Otake, Hisashi Masui, Hiroyuki Nakamura

    Chemistry a European Journal   Vol. 27 ( 27 ) page: 7525 - 7532   2021.1

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.202100059

  29. Cluster Preface: Integrated Synthesis Using Continuous-Flow Technologies Invited

    Fuse Shinichiro

    SYNLETT   Vol. 31 ( 19 ) page: 1878 - 1879   2020.12

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    Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0040-1706605

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  30. Recent Advances in Continuous-Flow Reactions Using Metal-Free Homogeneous Catalysts Invited Reviewed

    Naoto Sugisawa, Hiroyuki Nakamura, Shinichiro Fuse

    Catalysts   Vol. 10 ( 11 ) page: 1321   2020.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

  31. Innovation in peptide syntheses accelerated by micro-flow technologies

    Fuse Shinichiro

    MEDCHEM NEWS   Vol. 30 ( 4 ) page: 193 - 200   2020.11

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    Language:Japanese   Publisher:The Pharmaceutical Society of Japan  

    <p>Peptide drugs become increasingly important. In particular, specialty peptides including cyclic peptides and <i>N</i>-methylated peptides have garnered much attention in recent years. However, low cost production of these peptides has not been achieved. Nearly 140 years have passed since the first report of peptide bond formation by Theodor Curtius and numerous synthetic approaches have been developed for peptide syntheses. It seems like a very challenging task for making innovation in peptide syntheses. Micro-flow synthesis that uses thin channels as reaction space emerged in 1990’s. It provides new values for the uncontrollable reactions when using traditional batch reactors. Here, I introduce our amide bond formation using micro-flow technologies for accelerating innovation in peptide syntheses.</p>

    DOI: 10.14894/medchem.30.4_193

    CiNii Research

  32. Size-Controllable and Scalable Production of Liposomes Using a V-Shaped Mixer Micro-Flow Reactor

    Kawamura Jun, Kitamura Hiroshi, Otake Yuma, Fuse Shinichiro, Nakamura Hiroyuki

    ORGANIC PROCESS RESEARCH & DEVELOPMENT   Vol. 24 ( 10 ) page: 2122 - 2127   2020.10

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    Language:Japanese   Publisher:Organic Process Research and Development  

    The use of microfluidics has been regarded as a promising solution for the costly and complex preparation of liposomes, and the development of controllable and scalable liposome production using simple-structured, readily available, and inexpensive "off-the-shelf"microfluidics remains important pursuit. We have achieved simple and inexpensive production of liposomes using an off-the-shelf V-shaped mixer. The size of liposomes was controlled (50-70 nm diameter, PDI < 0.1) in the desired range (<100 nm) by changing the relative flow rate of the ethanol solution of lipids and the aqueous solution. The developed approach is scalable (12 mL/min), and several representative lipids, including inexpensive Span 60, can be used for the preparation of nanoparticles.

    DOI: 10.1021/acs.oprd.0c00174

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  33. Size-controllable and scalable production of liposomes using a V-shape mixer micro-flow reactor Invited Reviewed

    Jun Kawamura, Hiroshi Kitamura, Yuma Otake, Shinichiro Fuse, Hiroyuki Nakamura

    Organic Process Research and Development   Vol. 24 ( 10 ) page: 2122 - 2127   2020.6

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    Language:English   Publishing type:Research paper (scientific journal)  

  34. Investigation into the influence of an acrylic acid acceptor in organic D-π-A sensitizers against phototoxicity Reviewed

    Shinichiro Fuse, Wataru Moriya, Shinichi Sato, Hiroyuki Nakamura

    Bioorganic and Medicinal Chemistry   Vol. 28 ( 13 ) page: 115558   2020.5

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    DOI: 10.1016/j.bmc.2020.115558

  35. Photochemical Conversion of Isoxazoles to 5-Hydroxyimidazolines. Reviewed

    Taiki Morita, Shinichiro Fuse, Hiroyuki Nakamura

    Organic Letters   Vol. 22 ( 9 ) page: 3460 - 3463   2020.5

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    DOI: 10.1021/acs.orglett.0c00910

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  36. N-Methylated Peptide Synthesis via Acyl N-Methylimidazolium Cation Generation Accelerated by a Brønsted Acid. Reviewed

    Yuma Otake, Yusuke Shibata, Yoshihiro Hayashi, Susumu Kawauchi, Hiroyuki Nakamura, Shinichiro Fuse

    Angewandte Chemie (International ed. in English)   Vol. 59 ( 31 ) page: 12925 - 12930   2020.4

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    DOI: 10.1002/anie.202002106

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  37. Micro-flow synthesis of β-amino acid derivatives via a rapid dual activation approach. Reviewed

    Naoto Sugisawa, Hiroyuki Nakamura, Shinichiro Fuse

    Chemical communications (Cambridge, England)   Vol. 56   page: 4527 - 4530   2020.4

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    DOI: 10.1039/d0cc01403f

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  38. Single-Step, Rapid, and Mild Synthesis of beta-Amino Acid N-Carboxy Anhydrides Using Micro-Flow Technology

    Sugisawa Naoto, Otake Yuma, Nakamura Hiroyuki, Fuse Shinichiro

    CHEMISTRY-AN ASIAN JOURNAL   Vol. 15 ( 1 ) page: 79 - 84   2020.1

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    β-Amino acid N-carboxy anhydrides (β-NCAs) are rarely used in the synthesis of β-peptides, which is due mainly to the poor availability of these potentially useful substrates. Herein, we describe the heretofore challenging synthesis of β-NCAs via a single-step, rapid, and mild formation using pH flash switching and flash dilution, which are aspects of micro-flow technology. We synthesized 15 β-NCAs in good to excellent yields that included acid-labile β-NCAs that cannot be readily synthesized using the conventional Leuchs approach. Scaled-up synthesis using this process can be readily achieved via continuous operation.

    DOI: 10.1002/asia.201901429

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  39. Design, synthesis, and evaluation of indeno[2,1-c]pyrazolones for use as inhibitors against hypoxia-inducible factor (HIF)-1 transcriptional activity.

    Fuse S, Suzuki K, Kuchimaru T, Kadonosono T, Ueda H, Sato S, Kizaka-Kondoh S, Nakamura H

    Bioorganic & medicinal chemistry   Vol. 28 ( 1 ) page: 115207   2020.1

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    DOI: 10.1016/j.bmc.2019.115207

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  40. マイクロフロー合成技術による次世代医薬品(ペプチド)合成法の開発

    布施 新一郎

    月刊 PHARMSTAGE   Vol. 11   page: 13 - 22   2020

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  41. Design, synthesis, and evaluation of azo D–π-A dyes as photothermal agents Reviewed

    Shinichiro Fuse, Tsukasa Oishi, Keisuke Matsumura, Yoshihiro Hayashi, Susumu Kawauchi, Hiroyuki Nakamura

    Organic & Biomolecular Chemistry   Vol. 18 ( 1 ) page: 93 - 101   2019.12

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    DOI: 10.1039/c9ob02066g

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  42. The design, synthesis, and evaluation of azo D-π-A dyes as photothermal agents Reviewed

    Shinichiro Fuse, Tsukasa Oishi, Keisuke Matsumura, Yoshihiro Hayashi, Susumu Kawauchi, Hiroyuki Nakamura

    Organic and Biomolecular Chemistry   Vol. 18 ( 1 ) page: 93-101   2019.12

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  43. Single-step, rapid, and mild synthesis of β-amino acid N-carboxy anhydrides using micro-flow technology Reviewed

    Naoto Sugisawa, Yuma Otake, Hiroyuki Nakamura, and Shinichiro Fuse

    Chemistry an Asian Journal   Vol. 15 ( 1 ) page: 79-84   2019.11

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  44. Peptide chain elongation using unprotected amino acids in a micro-flow reactor Reviewed

    Shinichiro Fuse, Koshiro Masuda, Yuma Otake, Hiroyuki Nakamura

    Chemistry a European Journal   Vol. 25 ( 66 ) page: 15091-15097   2019.11

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  45. Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor Reviewed

    Shinichiro Fuse, Koshiro Masuda, Yuma Otake, Hiroyuki Nakamura

    Chemistry – A European Journal   Vol. 25 ( 66 ) page: 15091 - 15097   2019.11

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    DOI: 10.1002/chem.201903531

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  46. Design, synthesis, and evaluation of indeno[2,1-c]pyrazolones for use as inhibitors against hypoxia-inducible factor (HIF)-1 transcriptional activity Reviewed

    Shinichiro Fuse, Kensuke Suzuki, Takahiro Kuchimaru, Tetsuya Kadonosono, Hiroki Ueda, Shinichi Sato, Shinae Kizaka-Kondo, and Hiroyuki Nakamura

    Bioorganic and Medicinal Chemistry   Vol. 28   page: 115207   2019.11

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  47. Cover Feature: Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor (Chem. Eur. J. 66/2019) Reviewed

    Shinichiro Fuse, Koshiro Masuda, Yuma Otake, Hiroyuki Nakamura

    Chemistry – A European Journal     2019.11

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    DOI: 10.1002/chem.201904370

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  48. Donor-acceptor polymers containing thiazole-fused benzothiadiazole acceptor units for organic solar cells Reviewed

    Tomoya Nakamura, Yasuhisa Ishikura, Noriko Arakawa, Megumi Hori, Motoi Satou, Masaru Endo, Hisashi Masui, Shinichiro Fuse, Takashi Takahashi, Yasujiro Murata, Richard Murdey, Atsushi Wakamiya

    RSC Advances   Vol. 9 ( 13 ) page: 7107-7114   2019.3

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  49. Donor-acceptor polymers containing thiazole-fused benzothiadiazole acceptor units for organic solar cells.

    Nakamura T, Ishikura Y, Arakawa N, Hori M, Satou M, Endo M, Masui H, Fuse S, Takahashi T, Murata Y, Murdey R, Wakamiya A

    RSC advances   Vol. 9 ( 13 ) page: 7107 - 7114   2019.3

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    DOI: 10.1039/c9ra00229d

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  50. Peptide Synthesis Utilizing Micro-flow Technology Reviewed

    Shinichiro Fuse, Yuma Otake, Hiroyuki Nakamura

    Chemistry - An Asian Journal   Vol. 13 ( 24 ) page: 3818 - 3832   2018.12

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    DOI: 10.1002/asia.201801488

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  51. Elucidating the mode of action for thiophene-based organic D-π-A sensitizers for use in photodynamic therapy Reviewed

    Shinichiro Fuse, Miori Takizawa, Shinichi Sato, Shigetoshi Okazaki, Hiroyuki Nakamura,

    Bioorganic and Medicinal Chemistry   Vol. 27 ( 2 ) page: 315-321   2018.12

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  52. Synthesis of 3-hydroxy-4-substituted-picolinonitriles from 4-propargylaminoisoxazoles via stepwise and one-pot isoxazolopyridine formation/N-O bond cleavage sequence Reviewed

    Shintaro Fukuhara, Somaraju Yugandar, Shinichiro Fuse, Hiroyuki Nakamura

      Vol. 3 ( 12 ) page: 16472-16476   2018.12

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  53. The design, synthesis, and evaluation of organic dithienopyrrole-based D-pai-A dyes for use as sensitizers in photodynamic therapy Reviewed

    Shinichiro Fuse, Keisuke Matsumura, Miori Takizawa, Shinichi Sato, Hiroyuki Nakamura,

    Bioorganic and Medicinal Chemistry Letters   Vol. 28 ( 18 ) page: 3099-3104   2018.10

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  54. The design, synthesis, and evaluation of organic dithienopyrrole-based D-π-A dyes for use as sensitizers in photodynamic therapy Reviewed

    Shinichiro Fuse, Keisuke Matsumura, Miori Takizawa, Shinichi Sato, Hiroyuki Nakamura

    Bioorganic and Medicinal Chemistry Letters   Vol. 28 ( 18 ) page: 3099 - 3104   2018.10

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    © 2018 Elsevier Ltd Dithienopyrrole-based organic dyes that combine an electron-donating moiety (D), a π-conjugated bridge moiety (π), and an electron-accepting moiety (A) were designed and synthesized in short steps by previously developed one-pot Suzuki-Miyaura coupling approach. Absorption wavelengths of the dyes were readily tuned by altering the D and A moieties. The use of a strongly electron-withdrawing cyanopyridone acceptor enabled NIR absorption. A synthesized sensitizer, 2j, exerted potent phototoxicity mainly via a Type I mechanism in cells. A nitrogen atom in the dithienopyrrole ring serves as a connecting point for the introduction of functional building blocks that can improve the properties of sensitizers, which makes this D-π-A sensitizer a valuable template for the further development of sensitizers.

    DOI: 10.1016/j.bmcl.2018.07.025

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  55. Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor. Reviewed

    Otake Yuma, Nakamura Hiroyuki, Fuse Shinichiro

    Angewandte Chemie (International ed. in English)   Vol. 57 ( 35 ) page: 11389 - 11393   2018.8

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    DOI: 10.1002/anie.201803549

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  56. Recent advances in the integrated micro-flow synthesis containing photochemical reactions Reviewed

    Yuma Otake, Hiroyuki Nakamura, Shinichiro Fuse

    Tetrahedron Letters   Vol. 59 ( 18 ) page: 1691 - 1697   2018.5

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    Micro-flow photochemical reactions have great advantage over batch photochemical reactions due to its high light-penetration efficiency. Integrated micro-flow reaction enables efficient synthesis of structurally complex compounds from simple starting materials and it can avoid handling of explosive, toxic, unstable, or odorous intermediates. Combination of micro-flow photochemical reactions with integrated micro-flow synthesis enhances their benefits. Here we summarize recently reported integrated multi-step micro-flow synthesis containing various photochemical reactions.

    DOI: 10.1016/j.tetlet.2018.03.019

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  57. Synthesis of Pyrazolofuropyrazine via One-Pot S <inf>N</inf> Ar Reaction and Intramolecular Direct C-H Arylation Reviewed

    Shinichiro Fuse, Megumi Inaba, Shinichi Sato, Manjusha Joshi, Hiroyuki Nakamura

    Synthesis (Germany)   Vol. 50 ( 7 ) page: 1493 - 1498   2018.4

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    © Georg Thieme Verlag Stuttgart New York. Fused-ring systems containing heterocycles are attractive templates for drug discovery. Biologically active 6-5-5+6 fused-ring systems that possess heterocycles are available, but these require a relatively large number of synthetic steps for preparation. Therefore, pyrazolofuropyrazine was designed as a 6-5-5+6 ring system template that incorporates ready accessibility for drug discovery. Pyrazolofuropyrazines were successfully constructed in only a few steps via one-pot S N Ar reaction/intramolecular C-H direct arylation. As a drug candidate, pyrazolofuropyrazine has earned a favorable LogP, although significant biological activity has yet to be established; the ready accessibility of pyrazolofuropyrazine template, however, offers an opportunity for the rapid development of promising new drug candidates.

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  58. Recent progresses in the synthesis of functionalized isoxazoles Reviewed

    Taiki Morita, Somaraju Yugandar, Shinichiro Fuse, Hiroyuki Nakamura

    TETRAHEDRON LETTERS   Vol. 59 ( 13 ) page: 1159 - 1171   2018.3

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    Isoxazole is an important pharmacophore that is critical for biological activity. The isoxazole ring ranks 33rd in frequency among the 351 ring systems found in marketed drugs, thus suggesting a great deal of interest in the synthesis of functional isoxazoles. In recent years, various approaches have been developed for the synthesis and functionalization of isoxazoles. This comprehensive survey summarizes the recent new synthetic approaches to functionalized isoxazoles, with particular focus on the last three years with regard to the following reaction types: (1) 1,3-dipolar cycloaddition, (2) condensation, (3) cycloisomerization, and (4) direct functionalization. (C) 2018 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2018.02.020

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  59. D–π–A Dyes that Contain New Hydantoin Anchoring Groups for Dye-Sensitized Solar Cells Reviewed

    Hisashi Masui, Masato M. Maitani, Shinichiro Fuse, Ayaka Yamamura, Yuhei Ogomi, Shuzi Hayase, Tatsuo Kaiho, Hiroshi Tanaka, Yuji Wada, Takashi Takahashi

    Asian Journal of Organic Chemistry   Vol. 7 ( 2 ) page: 458 - 464   2018.2

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    The development of new anchoring groups is important to facilitate effective co-sensitization in dye-sensitized solar cells (DSSCs). Herein, stable organic D–π–A dyes that contain new heterocyclic hydantoin-based anchoring groups have been designed, synthesized, and used in DSSCs. These dye sensitizers were evaluated in terms of their absorption spectra, electrochemical properties, and performance in DSSC devices. Although only one-third of the amount of hydantoin-containing dyes adsorbed onto TiO2 relative to their cyanoacrylic-acid-containing analogues, they exhibited effective photoexcited electron-transfer properties. External quantum efficiencies of over 80 % was observed, which were comparable to those of the cyanoacrylic-acid-containing dyes. In addition, the new hydantoin-containing dyes exhibited significant robustness, which could allow improved stability of their corresponding photovoltaic devices under harsh conditions, such as high temperature and humidity.

    DOI: 10.1002/ajoc.201700542

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  60. Gold(I)-Catalyzed Intramolecular SEAr Reaction: Efficient Synthesis of Isoxazole-Containing Fused Heterocycles Reviewed

    Taiki Morita, Shintaro Fukuhara, Shinichiro Fuse, Hiroyuki Nakamura

    ORGANIC LETTERS   Vol. 20 ( 2 ) page: 433 - 436   2018.1

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    Intramolecular electrophilic aromatic substitution (SEAr) reaction at the 5-position of isoxazoles was achieved. The electron-donating heteroatoms (N and O) at the 4-position of isoxazoles, which can be readily prepared based on our originally developed synthetic procedure, and a cationic gold(I) catalyst are essential for the intramolecular SEAr reaction to synthesize isoxazole-containing fused heterocycles. Structurally diverse isoxazolopyridines 6 and isoxazolopyrans 9, including base-labile 3-unsubstituted derivatives, were synthesized in good to high yields. The addition of N-phenylbenzaldimine as a hydrogen acceptor improved yields in the synthesis of isoxazolopyridines. Furthermore, synthesis of the tetracyclic fused ring system 12 was achieved by tandem cyclization from the corresponding diyne 11.

    DOI: 10.1021/acs.orglett.7b03760

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  61. Integrated Micro-Flow Synthesis Based on Photochemical Wolff Rearrangement Reviewed

    Shinichiro Fuse, Yuma Otake, Hiroyuki Nakamura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   Vol. 2017 ( 44 ) page: 6466 - 6473   2017.12

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    The Wolff rearrangement of -diazo carbonyl compounds has remained important in organic synthesis since its development more than 115 years ago. The risks involved in handling diazo compounds can be minimized by utilizing micro-flow technology. In addition, photochemical Wolff rearrangement can be carried out efficiently with the aid of micro-flow technology. Integrated micro-flow synthesis is therefore well-suited to the preparation of -diazo carbonyl compounds and their photochemical Wolff rearrangement. This review article summarizes recently reported micro-flow photochemical Wolff rearrangements and their application in integrated micro-flow syntheses.

    DOI: 10.1002/ejoc.201700789

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  62. Photodynamic therapy using a cytotoxic photosensitizer porphyrus envelope that targets the cell membrane Reviewed

    Mizuho Inai, Norihiro Honda, Hisanao Hazama, Sharmin Akter, Shinichiro Fuse, Hiroyuki Nakamura, Tomoyuki Nishikawa, Yasufumi Kaneda, Kunio Awazu

    PHOTODIAGNOSIS AND PHOTODYNAMIC THERAPY   Vol. 20   page: 238 - 245   2017.12

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    Background: Subcellular localization of a photosensitizer is known to determine the therapeutic efficacy of photodynamic therapy (PDT). Cell membrane is an optimal target that promises an effective treatment outcome. Objectives: We previously developed a novel photosensitizer named porphyrus envelope (PE) by combining hemagglutinating virus of Japan envelope (HVJ-E) with lipidated protoporphyrin IX (PpIX lipid). In the current study, the cellular localization of PE and its ability to induce multiple anti-tumor effect were characterized.
    Materials and Methods: The localization and uptake of PpIX lipid in cells were evaluated with confocal laser scanning microscopy and a cell-based fluorescent assay, respectively. The ability of PE to suppress the migration and proliferation of cancer cells was assessed using a scratch-wound assay. The synergistic effect of PDT and HVJ-E treatment was evaluated using an in vitro experiment with PC-3 cells.
    Results: PE localized along the cell membrane and PpIX lipid accumulated selectively in the prostate cancer cells within 10 min. Also, PE maintained the ability to undergo fusion and induce cancer cell death even after light irradiation at the dose for PDT. Incubation with PE resulted in delayed migratory and proliferative activity of PC 3 cells. PE-mediated PDT was twice as effective when cells were further incubated with PE following PDT.
    Conclusions: PE allows rapid drug delivery targeting the cell membrane. Because the cytotoxicity of HVJ-E was maintained, synergistic effect of HVJ-E and the photochemical reactions resulted in highly effective killing of prostate cancer cells in vitro and thus represents a promising treatment for prostate cancer.

    DOI: 10.1016/j.pdpdt.2017.10.017

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  63. Systematic Synthesis of Thiophene-based, Organic Donor-pi-Acceptor Dyes and Elucidation of Their Structure-Function Relationship Reviewed

    Shinichiro Fuse

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 75 ( 9 ) page: 49 - 62   2017.9

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    Thiophene-based organic D-pi-A dyes exert various functions as sensitizers of dye-sensitized solar cells, p-type semiconductors of thin-film organic solar cells, and inhibitors of aggregation of amyloid-beta and tau proteins those are regarded as promising drug targets of Alzheimer's disease. This account describes rapid and systematic synthesis of thiophene-based organic D-pi-A dyes via our developed, one-pot, cross-coupling approach and evaluation of their various functions in order to acquire high-quality structure-function relationship information.

    DOI: 10.5059/yukigoseikyokaishi.75.941

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  64. Thiophene-Based Organic D-pi-A Dyes as Potent Sensitizers for Photodynamic Therapy Reviewed

    Shinichiro Fuse, Miori Takizawa, Keisuke Matsumura, Shinichi Sato, Shigetoshi Okazaki, Hiroyuki Nakamura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 34 ) page: 5170 - 5177   2017.9

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    In this study, synthetically readily accessible, thiophene-based organic D--A sensitizers exerted high phototoxicity and are valuable as sensitizer templates for use in photodynamic therapy (PDT). Evaluation of the antitumor activity of our previously synthesized D--A sensitizers under photoirradiation revealed their potent phototoxicity. The structural requirements of the D--A sensitizer for phototoxicity were elucidated with the rapid synthesis of structurally simplified analogues and evaluation of their antitumor activity under photoirradiation. Our developed sensitizers mainly accumulated in mitochondria and damaged cancer cells through both Type I and Type II mechanisms. The developed new template could be useful in the future development of sensitizers that could fulfil the requirements for PDT.

    DOI: 10.1002/ejoc.201701019

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  65. Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C-H Direct Arylations Reviewed

    Shinichiro Fuse, Taiki Morita, Hiroyuki Nakamura

    SYNTHESIS-STUTTGART   Vol. 49 ( 11 ) page: 2351 - 2360   2017.6

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    Functionalized isoxazoles are important as pharmaceuticals and agrochemicals. Generally, electrophilic aromatic substitution or generation of carbanions/electrophilic trapping approach is used to introduce functional groups into unsubstituted heteroaromatics. However, these approaches have not been simple to apply to unsubstituted isoxazoles due to their poor nucleophilicity and instability under basic conditions. Recently several approaches have been reported to overcome these problems. This review summarizes the functionalization of isoxazoles, including SEAr reactions and C-H direct arylations, towards the step-by-step multifunctionalization of isoxazoles.

    DOI: 10.1055/s-0036-1588784

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  66. Solution-phase automated synthesis of an alpha-amino aldehyde as a versatile intermediate Reviewed

    Hisashi Masui, Sae Yosugi, Shinichiro Fuse, Takashi Takahashi

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 13   page: 106 - 110   2017

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    A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

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  67. Total synthesis and stereochemistry revision of mannopeptimycin aglycone Reviewed

    Shinichiro Fuse, Hiroshi Tanaka, Takashi Takahashi, Takayuki Doi

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   Vol. 75 ( 12 ) page: 1274 - 1285   2017

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    Mannopeptimycin is an attractive drug candidate due to its strong antimicrobial activity against drug-resistant strains. However, detailed elucidation of structure - activity relationship and its mode of action has been hampered because the chemical synthesis of the densely functionalized aglycone moiety consisting of cyclic hexapeptide was not established. The key point in the synthesis of the aglycone was the construction of densely functionalized unnatural amino acids, Aiha-A and Aiha-B. This account describes isolation, structural determination of mannopepti-mycins, previously reported synthesis of Aiha-A and Aiha-B as well as our short-step, high-yielding synthesis of Aihas leading to the first synthesis of mannopeptimycin aglycone with stereochemistry revision of originally proposed structure.

    DOI: 10.5059/yukigoseikyokaishi.75.1274

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Books 44

  1. 生体分子や医薬品をつくるための化学 ペプチド・タンパク質の化学合成

    林剛介、佐藤浩平、真木勇太、布施新一郎( Role: Joint author ,  ケミカルバイオロジーの冒険第8回 現代化学, (11))

    東京化学同人  2024.11 

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    Responsible for pages:31-37   Language:Japanese Book type:Scholarly book

  2. 有機化学:自動合成の最新動向

    布施新一郎( Role: Contributor ,  第IV部10)

    東京化学同人  2024.3 

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    Total pages:7   Responsible for pages:68-74   Language:Japanese Book type:General book, introductory book for general audience

  3. ペプチドの超高効率フロー合成法

    布施新一郎( Role: Sole author ,  あなたのラボから薬を生み出す~アカデミア創薬の実践~)

    羊土社  2024.2 

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    Total pages:7   Responsible for pages:157-163   Language:Japanese Book type:Scholarly book

  4. 有機合成化学における実験自動化、データサイエンス利用の最前線

    布施新一郎( Role: Sole author)

    日本薬学会  2023.9 

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    Total pages:6   Responsible for pages:825-830   Language:Japanese Book type:Scholarly book

  5. N-メチル化ペプチドのマイクロフロー合成法開発 Reviewed

    布施新一郎( Role: Contributor ,  66)

    化学同人  2023.7 

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    Total pages:2   Responsible for pages:132-133   Language:Japanese Book type:General book, introductory book for general audience

  6. ベイズ最適化を駆使したマイクロフロー反応での条件探索

    布施新一郎( Role: Sole author)

    化学工学会  2023.7 

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    Total pages:4   Responsible for pages:293-296   Language:Japanese Book type:Scholarly book

  7. リン酸トリエステル合成の変革期

    増井悠、布施新一郎( Role: Joint author ,  月刊化学 注目のトピックス)

    化学同人  2023.1 

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    Total pages:2   Responsible for pages:64-65   Language:Japanese Book type:Scholarly book

  8. 特殊中分子ペプチド医薬のマイクロフロー合成

    布施新一郎( Role: Sole author ,  中分子ペプチド医薬で新たな標的を狙う!! ~新章を迎えた創薬モダリティ~ (1))

    羊土社  2023.1 

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    Total pages:6   Responsible for pages:39-44   Language:Japanese Book type:Scholarly book

  9. フロー・自動合成・機械学習を駆使する有機合成

    布施新一郎( Role: Sole author)

    大阪工研協会  2022.11 

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    Responsible for pages:366-372   Language:Japanese Book type:Scholarly book

  10. Continuous-flow synthesis of N-methylated peptides via generation of an acyl N-methylimidazolium cation

    Hisashi Masui, Shinichiro Fuse( Role: Joint author)

    Springer Nature  2022.6  ( ISBN:978-1-0716-2489-0

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    Total pages:9   Responsible for pages:45-53   Language:English Book type:Scholarly book

    DOI: 10.1007/978-1-0716-2489-0_4

  11. 研究開発部門へのDX導入によるR&Dの効率化、実験の短縮化

    布施新一郎( Role: Joint author ,  第4章3節 有機合成化学における自動合成技術、フロー合成技術、機械学習の活用)

    技術情報協会  2022.4 

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    Responsible for pages:428-441   Language:Japanese Book type:Scholarly book

  12. ベイズ最適化を用いた反応条件探索の効率化

    杉澤直斗、布施新一郎( Role: Joint author ,  月刊 月刊研究開発リーダー(193))

    技術情報協会  2022.4 

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    Total pages:3   Responsible for pages:10-12   Language:Japanese Book type:Scholarly book

  13. ペプチド合成

    布施新一郎、増井悠( Role: Joint author ,  フローマイクロ合成の最新動向 第3編第12章)

    シーエムシー出版  2021.8 

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    Responsible for pages:122-136   Language:Japanese Book type:Scholarly book

  14. Efficient synthesis of biologically active peptides based on micro-flow amide bond formation peptide synthesis utilizing micro-flow technology

    Shinichiro Fuse( Role: Sole author)

    Springer Nature  2021.7  ( ISBN:978-981-16-2458-2

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    Total pages:22   Responsible for pages:139-160   Language:English Book type:Scholarly book

    DOI: 10.1007/978-981-16-2458-2_9

  15. 創薬における有機合成の自動化について考える

    布施新一郎( Role: Sole author ,  ~特集新型コロナで変わる時代の実験自動化・遠隔化~ (1))

    羊土社  2020.12 

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    Total pages:5   Responsible for pages:13-17   Language:Japanese Book type:Scholarly book

  16. フローマイクロリアクターによるペプチド合成

    布施新一郎( Role: Sole author ,  フロー合成、連続生産のプロセス設計、条件設定と応用事例 第6章8節)

    技術情報協会  2020.12 

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    Total pages:6   Responsible for pages:300-315   Language:Japanese Book type:Scholarly book

  17. 入手容易なマイクロミキサーを用いたリポソームの調製法開発

    北村宙士、小竹佑磨、川村淳、布施新一郎、中村浩之( Role: Joint author ,  製剤機械技術学会誌 29 (4))

    製剤機械技術学会  2020.12 

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    Total pages:7   Responsible for pages:407-413   Language:Japanese Book type:Scholarly book

  18. 自動化はどこからきたのか 自動化は何者か 自動化はどこへ行くのか~有機合成の自動化を考える~

    布施新一郎( Role: Sole author ,  現代化学 (11))

    東京化学同人  2020.11 

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    Total pages:3   Responsible for pages:36-38   Language:Japanese Book type:Scholarly book

  19. マイクロフロー合成技術による次世代医薬品(ペプチド)合成法の開発

    布施新一郎( Role: Sole author ,  月刊 PHARMSTAGE (11))

    技術情報協会  2020.11 

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    Total pages:10   Responsible for pages:13-22   Language:Japanese Book type:Scholarly book

  20. マイクロフロー合成法を駆動力とするペプチド合成の革新

    布施新一郎( Role: Sole author ,  MEDCHEM NEWS 30 (4))

    日本薬学会 医薬化学部会  2020.11 

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    Total pages:7   Responsible for pages:193-199   Language:Japanese Book type:Scholarly book

  21. 化学合成法

    (医薬品開発における中分子領域(核酸医薬・ペプチド医薬品)における開発戦略 第3章1節 ペプチド医薬品における各合成の概要 1.)

    情報機構  2019 

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    Responsible for pages:113-120  

  22. マイクロフローアミド化法を基盤とする高効率ペプチド合成法の開発

    布施新一郎(触媒技術の動向と展望2019 1 [3-4] (b))

    触媒学会  2019 

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    Responsible for pages:124-134  

  23. マイクロフロー法によるペプチド合成

    布施新一郎(月刊ファインケミカル, 48, (1))

    シーエムシー出版  2019 

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    Responsible for pages:13-21  

  24. 実践光化学

    布施新一郎(光化学フロンティア 未来材料を生む有機光化学の基礎 第III部実用編 第18章)

    化学同人  2018 

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    Responsible for pages:388-399  

  25. フローマイクロリアクターによるペプチド合成

    布施新一郎(ペプチド医薬品開発のためのスクリーニング・安定化・製剤化技術 第4章3節)

    技術情報協会  2018 

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    Responsible for pages:162-173  

  26. Recent progresses in the synthesis of functionalized isoxazoles

    Taiki Morita, Somaraju Yugandar, Shinichiro Fuse, Hiroyuki Nakamura(Tetrahedron Lett. 59 (13))

    Elsevier  2018 

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    Responsible for pages:1159-1171  

  27. Recent advances in the integrated micro-flow synthesis containing photochemical reactions

    Yuma Otake, Hiroyuki Nakamura, Shinichiro Fuse(Tetrahedron Lett. 59 (18))

    Elsevier  2018 

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    Responsible for pages:1691-1697  

  28. Peptide synthesis utilizing micro-flow technology

    Shinichiro Fuse, Yuma Otake, Hiroyuki Nakamura,(Chem. Asian J. 13 (24))

    Wiley-VCH  2018 

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    Responsible for pages:3818-3832  

  29. マンノペプチマイシンアグリコンの合成と立体化学訂正

    布施新一郎、田中浩士、高橋孝志、土井隆行(有機合成化学協会誌 75 (9))

    有機合成化学協会  2017 

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    Responsible for pages:941-954  

  30. Step-by-step multifunctionalization of isoxazoles based on SEAr reactions and C-H direct arylations

    Shinichiro Fuse, Taiki Morita, Hiroyuki Nakamura,(2351-2360)

    Thieme  2017 

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    Responsible for pages:2351-2360  

  31. Integrated micro-flow synthesis based on photochemical Wolff rearrangement

    Shinichiro Fuse, Yuma Otake, Hiroyuki Nakamura(Eur. J. Org. Chem. (44))

    2017 

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    Responsible for pages:6466-6473  

  32. コンビナトリアル科学を基盤とする材料開発

    増井悠、布施新一郎、高橋孝志(OrganoMetalicNEWS (3))

    近畿化学協会 有機金属部会  2015 

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    Responsible for pages:100-104  

  33. マイクロフロー光反応・イミドイル化反応を駆使する効率的な有機合成

    布施新一郎、高橋孝志(有機合成化学協会誌 73 (5))

    有機合成化学協会  2015 

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    Responsible for pages:442-451  

  34. サイト選択的マイクロフロー反応を駆使する天然物合成

    布施新一郎(化学と工業, 飛翔する若手研究者68, (8))

    日本化学会  2015 

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    Responsible for pages:733-734  

  35. 担持反応剤による反応

    布施新一郎、高橋孝志(フロー・マイクロ合成, 基礎から実際の合成・製造まで 第17章)

    化学同人  2014 

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    Responsible for pages:203-215  

  36. マイクロフローリアクターを駆使したペプチドの迅速合成

    布施新一郎、高橋孝志(現代化学, (7))

    東京化学同人  2014 

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    Responsible for pages:24-28  

  37. Micro-flow technology: Another solution for the site-selective modification of multi-functionalized molecules

    Shinichiro Fuse, Yuto Mifune, Nobutake Tanabe, Takashi Takahashi(Synlett Synpacts 25 (15))

    Thieme  2014 

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    Responsible for pages:2087-2092  

  38. ケミカルバイオロジーのための化合物群合成

    布施新一郎、高橋孝志(ケミカルバイオロジー, 成功事例から学ぶ研究戦略 第3章)

    丸善出版  2013 

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    Responsible for pages:46-60  

  39. マイクロフロー合成法を駆使する有機合成

    布施新一郎(有機合成化学協会誌 70 (2))

    有機合成化学協会  2012 

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    Responsible for pages:177-178  

  40. Efficient synthesis of natural products aided by automated synthesizers and microreactors

    Shinichiro Fuse, Kazuhiro Machida, Takashi Takahashi(New Strategies in Chemical Synthesis and Catalysis, chapter 2)

    Wiley-VCH  2012 

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    Responsible for pages:33-56  

  41. 天然物を基盤としたケミカルバイオロジー研究を加速させる合成工学的新技術

    布施新一郎、高橋孝志(化学工業, 62)

    化学工業社  2011 

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    Responsible for pages:7-13  

  42. ラボオートメーション技術を活用したタキソールおよび9員環エンジイン化合物の合成

    高橋孝志、布施新一郎(天然物全合成の最新動向 V 生物活性天然物の高効率大量合成)

    シーエムシー出版  2007 

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    Responsible for pages:279-292  

  43. タキソール

    布施新一郎、土井隆行、高橋孝志(天然物化学 -植物編- 3.1.4)

    アイピーシー  2007 

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    Responsible for pages:301-310  

  44. 合成ロボットを使った天然物合成

    高橋孝志、布施新一郎(化学フロンティア 14)

    化学同人  2004 

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    Responsible for pages:66-73  

▼display all

MISC 73

  1. Recent advances in continuous-flow reactions using metal-free homogeneous catalysts Invited Reviewed

    Naoto Sugisawa, Hiroyuki Nakamura, Shinichiro Fuse

    Catalysts   Vol. 10 ( 11 ) page: 1321   2020.11

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    Authorship:Lead author   Language:English  

    DOI: 10.3390/catal10111321

  2. Peptide Synthesis Utilizing Micro-flow Technology Reviewed

    Shinichiro Fuse, Yuma Otake, Hiroyuki Nakamura

    Chemistry - An Asian Journal     2018.11

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  3. Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor. Reviewed

    Otake Yuma, Nakamura Hiroyuki, Fuse Shinichiro

    Angewandte Chemie (International ed. in English)   Vol. 57 ( 35 ) page: 11389   2018.8

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  4. D-pi-A Dyes that Contain New Hydantoin Anchoring Groups for Dye-Sensitized Solar Cells Reviewed

    Masui Hisashi, Maitani Masato M, Fuse Shinichiro, Yamamura Ayaka, Ogomi Yuhei, Hayase Shuzi, Kaiho Tatsuo, Tanaka Hiroshi, Wada Yuji, Takahashi Takashi

    Asian Journal of Organic Chemistry   Vol. 7 ( 2 ) page: 458-464   2018

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  5. Gold(I)-Catalyzed Intramolecular SEAr Reaction: Efficient Synthesis of Isoxazole-Containing Fused Heterocycles Reviewed

    Morita Taiki, Fukuhara Shintaro, Fuse Shinichiro, Nakamura Hiroyuki

    Organic Letters   Vol. 20 ( 2 ) page: 433-436   2018

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  6. Recent advances in the integrated micro-flow synthesis containing photochemical reactions Reviewed

    Otake Yuma, Nakamura Hiroyuki, Fuse Shinichiro

    Tetrahedron Letters   Vol. 59 ( 18 ) page: 1691-1697   2018

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  7. Recent progresses in the synthesis of functionalized isoxazoles Reviewed

    Morita Taiki, Yugandar Somaraju, Fuse Shinichiro, Nakamura Hiroyuki

    Tetrahedron Letters   Vol. 59 ( 13 ) page: 1159-1171   2018

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  8. Synthesis of Pyrazolofuropyrazine via One-Pot SNAr Reaction and Intramolecular Direct C-H Arylation Reviewed

    Fuse Shinichiro, Inaba Megumi, Sato Shinichi, Joshi Manjusha, Nakamura Hiroyuki

    Synthesis-Stuttgart   Vol. 50 ( 7 ) page: 1493-1498   2018

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  9. The design, synthesis, and evaluation of organic dithienopyrrole-based D-pi-A dyes for use as sensitizers in photodynamic therapy. Reviewed

    Fuse Shinichiro, Matsumura Keisuke, Takizawa Miori, Sato Shinichi, Nakamura Hiroyuki

    Bioorganic & medicinal chemistry letters     2018

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  10. Integrated Micro-Flow Synthesis Based on Photochemical Wolff Rearrangement Reviewed

    Fuse Shinichiro, Otake Yuma, Nakamura Hiroyuki

    European Journal of Organic Chemistry   Vol. 2017 ( 44 ) page: 6466-6473   2017.12

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  11. Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone Reviewed

    Fuse Shinichiro, Tanaka Hiroshi, Takahashi Takashi, Doi Takayuki

    Journal of Synthetic Organic Chemistry Japan   Vol. 75 ( 12 ) page: 1274-1285   2017

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  12. Photodynamic therapy using a cytotoxic photosensitizer porphyrus envelope that targets the cell membrane Reviewed

    Inai Mizuho, Honda Norihiro, Hazama Hisanao, Akter Sharmin, Fuse Shinichiro, Nakamura Hiroyuki, Nishikawa Tomoyuki, Kaneda Yasufumi, Awazu Kunio

    Photodiagnosis and Photodynamic Therapy   Vol. 20   page: 238-245   2017

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  13. Solution-phase automated synthesis of an alpha-amino aldehyde as a versatile intermediate Reviewed

    Masui Hisashi, Yosugi Sae, Fuse Shinichiro, Takahashi Takashi

    Beilstein Journal of Organic Chemistry   Vol. 13   page: 106-110   2017

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  14. Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C-H Direct Arylations Reviewed

    Fuse Shinichiro, Morita Taiki, Nakamura Hiroyuki

    Synthesis-Stuttgart   Vol. 49 ( 11 ) page: 2351-2360   2017

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  15. Systematic Synthesis of Thiophene-based, Organic Donor-pi-Acceptor Dyes and Elucidation of Their Structure-Function Relationship Reviewed

    Fuse Shinichiro

    Journal of Synthetic Organic Chemistry Japan   Vol. 75 ( 9 ) page: 49-62   2017

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  16. Thiophene-Based Organic D-pi-A Dyes as Potent Sensitizers for Photodynamic Therapy Reviewed

    Fuse Shinichiro, Takizawa Miori, Matsumura Keisuke, Sato Shinichi, Okazaki Shigetoshi, Nakamura Hiroyuki

    European Journal of Organic Chemistry   ( 34 ) page: 5170-5177   2017

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  17. 6-Azido-6-deoxy-L-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes Reviewed

    Hamagami Hiroki, Kumazoe Motofumi, Yamaguchi Yoshiki, Fuse Shinichiro, Tachibana Hirofumi, Tanaka Hiroshi

    Chemistry-a European Journal   Vol. 22 ( 36 ) page: 12884-12890   2016

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  18. A rapid and clean synthetic approach to cyclic peptides via micro-flow peptide chain elongation and photochemical cyclization: synthesis of a cyclic RGD peptide Reviewed

    Mifune Yuto, Nakamura Hiroyuki, Fuse Shinichiro

    Organic & Biomolecular Chemistry   Vol. 14 ( 47 ) page: 11244-11249   2016

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  19. Development of 1-aryl-3-furanyl/thienyl-imidazopyridine templates for inhibitors against hypoxia inducible factor (HIF)-1 transcriptional activity Reviewed

    Fuse Shinichiro, Ohuchi Toshiaki, Asawa Yasunobu, Sato Shinichi, Nakamura Hiroyuki

    Bioorganic & Medicinal Chemistry Letters   Vol. 26 ( 24 ) page: 5887-5890   2016

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  20. Generation of an 4-Isoxazolyl Anion Species: Facile Access to Multifunctionalized Isoxazoles Reviewed

    Morita Taiki, Fuse Shinichiro, Nakamura Hiroyuki

    Angewandte Chemie-International Edition   Vol. 55 ( 43 ) page: 13580-13584   2016

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  21. Rapid Synthesis of D-A '-pi-A Dyes through a One-Pot Three-Component Suzuki-Miyaura Coupling and an Evaluation of their Photovoltaic Properties for Use in Dye-Sensitized Solar Cells Reviewed

    Irie Shunsuke, Fuse Shinichiro, Maitani Masato M, Wada Yuji, Ogomi Yuhei, Hayase Shuzi, Kaiho Tatsuo, Masui Hisashi, Tanaka Hiroshi, Takahashi Takashi

    Chemistry-a European Journal   Vol. 22 ( 7 ) page: 2507-2514   2016

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  22. Synthesis and Evaluation of Thiophene-Based Organic Dyes Containing a Rigid and Nonplanar Donor with Secondary Electron Donors for Use in Dye-Sensitized Solar Cells Reviewed

    Fuse Shinichiro, Takahashi Ryota, Maitani Masato M, Wada Yuji, Kaiho Tatsuo, Tanaka Hiroshi, Takahashi Takashi

    European Journal of Organic Chemistry   ( 3 ) page: 508-517   2016

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  23. Synthesis of Asymmetrical-Terminally Bifunctionlized Alkanes by Sequential Suzuki-Miyaura Coupling Using B-Thexylboracyclanes Reviewed

    Suzuki Ryota, Fuse Shinichiro, Tanaka Hiroshi

    European Journal of Organic Chemistry   ( 21 ) page: 3478-3481   2016

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  24. The -Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect Reviewed

    Aoyagi Taku, Ohira Shuichi, Fuse Shinichiro, Uzawa Jun, Yamaguchi Yoshiki, Tanaka Hiroshi

    Chemistry-a European Journal   Vol. 22 ( 20 ) page: 6968-6973   2016

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  25. The Design, Synthesis, and Evaluation of 1,5,7-Trisubstituted-3-Pyridyl-Xanthones for Use as Insecticides Starting from PyripyropeneA Reviewed

    Fuse Shinichiro, Matsumura Keisuke, Johmoto Kohei, Uekusa Hidehiro, Tanaka Hiroshi, Hirose Tomoyasu, Sunazuka Toshiaki, Omura Satoshi, Takahashi Takashi

    Chemistry-a European Journal   Vol. 22 ( 51 ) page: 18450-18455   2016

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  26. The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67LR Reviewed

    Shiraishi Nana, Kumazoe Motofumi, Fuse Shinichiro, Tachibana Hirofumi, Tanaka Hiroshi

    Chemistry-a European Journal   Vol. 22 ( 37 ) page: 13050-13053   2016

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  27. Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation Reviewed

    Fuse Shinichiro, Mifune Yuto, Nakamura Hiroyuki, Tanaka Hiroshi

    Nature Communications   Vol. 7   page: 13491   2016

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  28. Sequential SNAr Reaction/Suzuki-Miyaura Coupling/C-H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles Reviewed

    Morita Taiki, Kobayashi Daisuke, Matsumura Keisuke, Johmoto Kohei, Uekusa Hidehiro, Fuse Shinichiro, Takahashi Takashi

    Chemistry-an Asian Journal   Vol. 10 ( 8 ) page: 1626-1630   2015

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  29. Regioselective, One-Pot, Three-Component Synthesis of 1,3,4-and 1,3,5-Triarylpyrazoles from 1-and 2-Aryl-1-alkenyl Sulfones Reviewed

    Fuse Shinichiro, Sugiyama Hirotaka, Kobayashi Daisuke, Iijima Yusuke, Matsumura Keisuke, Tanaka Hiroshi, Takahashi Takashi

    European Journal of Organic Chemistry   ( 21 ) page: 4756-4764   2015

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  30. A Facile Preparation of alpha-Aryl Carboxylic Acid via One-Flow Arndt-Eistert Synthesis Reviewed

    Fuse Shinichiro, Otake Yuma, Mifune Yuto, Tanaka Hiroshi

    Australian Journal of Chemistry   Vol. 68 ( 11 ) page: 1657-1661   2015

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  31. Asymmetric Total Synthesis of ent-PyripyropeneA Reviewed

    Fuse Shinichiro, Ikebe Ayako, Oosumi Kazuya, Karasawa Tomoya, Matsumura Keisuke, Izumikawa Miho, Johmoto Kohei, Uekusa Hidehiro, Shin-ya Kazuo, Doi Takayuki, Takahashi Takashi

    Chemistry-a European Journal   Vol. 21 ( 26 ) page: 9454-9460   2015

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  32. Directing/Protecting-Group-Free Synthesis of Tetraaryl-Substituted Pyrazoles through Four Direct Arylations on an Unsubstituted Pyrazole Scaffold Reviewed

    Fuse Shinichiro, Morita Taiki, Johmoto Kohei, Uekusa Hidehiro, Tanaka Hiroshi

    Chemistry-a European Journal   Vol. 21 ( 41 ) page: 14370-14375   2015

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  33. Efficient Organic Synthesis based on Micro-flow Photo-reaction, Imidoylation, and Acylation Reviewed

    Fuse Shinichiro, Takahashi Takashi

    Journal of Synthetic Organic Chemistry Japan   Vol. 73 ( 5 ) page: 442-451   2015

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    Research data storage URL: http://orcid.org/0000-0002-6836-4180

  34. Facile, One-Step Synthesis of 5-Substituted Thieno[3,4-c]pyrrole-4,6-dione by Palladium-Catalyzed Carbonylative Amidation Reviewed

    Fuse Shinichiro, Takahashi Ryota, Takahashi Takashi

    European Journal of Organic Chemistry   ( 16 ) page: 3430-3434   2015

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  35. Palladium-catalyzed double carbonylation-based diversity-oriented synthesis of 3,4-dihydroisoquinoline-1-carboxamides Reviewed

    Masui Hisashi, Ishizawa Natsumi, Fuse Shinichiro, Takahashi Takashi

    Tetrahedron   Vol. 71 ( 37 ) page: 6354-6360   2015

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  36. Rapid Synthesis of Thiophene-Based, Organic Dyes for Dye-Sensitized Solar Cells (DSSCs) by a One-Pot, Four-Component Coupling Approach Reviewed

    Matsumura Keisuke, Yoshizaki Soichi, Maitani Masato. M, Wada Yuji, Ogomi Yuhei, Hayase Shuzi, Kaiho Tatsuo, Fuse Shinichiro, Tanaka Hiroshi, Takahashi Takashi

    Chemistry-a European Journal   Vol. 21 ( 27 ) page: 9742-9747   2015

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  37. Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone Reviewed

    Fuse Shinichiro, Koinuma Hirotsugu, Kimbara Atsushi, Izumikawa Miho, Mifune Yuto, He Haiyin, Shin-ya Kazuo, Takahashi Takashi, Doi Takayuki

    Journal of the American Chemical Society   Vol. 136 ( 34 ) page: 12011-12017   2014

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  38. Development of dual targeting inhibitors against aggregations of amyloid-beta and tau protein Reviewed

    Fuse Shinichiro, Matsumura Keisuke, Fujita Yuki, Sugimoto Hachiro, Takahashi Takashi

    European Journal of Medicinal Chemistry   Vol. 85   page: 228-234   2014

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  39. Efficient Amide Bond Formation through a Rapid and Strong Activation of Carboxylic Acids in a Microflow Reactor Reviewed

    Fuse Shinichiro, Mifune Yuto, Takahashi Takashi

    Angewandte Chemie-International Edition   Vol. 53 ( 3 ) page: 851-855   2014

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  40. Elucidating the Structure-Property Relationships of Donor-pi-Acceptor Dyes for Dye-Sensitized Solar Cells (DSSCs) through Rapid Library Synthesis by a One-Pot Procedure Reviewed

    Fuse Shinichiro, Sugiyama Sakae, Maitani Masato M, Wada Yuji, Ogomi Yuhei, Hayase Shuzi, Katoh Ryuzi, Kaiho Tatsuo, Takahashi Takashi

    Chemistry-a European Journal   Vol. 20 ( 34 ) page: 10685-10694   2014

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  41. Elucidation of the Structure-Property Relationship of p-Type Organic Semiconductors through Rapid Library Construction via a One-Pot, Suzuki-Miyaura Coupling Reaction Reviewed

    Fuse Shinichiro, Matsumura Keisuke, Wakamiya Atsushi, Masui Hisashi, Tanaka Hiroshi, Yoshikawa Susumu, Takahashi Takashi

    Acs Combinatorial Science   Vol. 16 ( 9 ) page: 494-499   2014

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  42. Microflow Technology: Another Solution for the Site-Selective Modification of Multifunctionalized Molecules Reviewed

    Fuse Shinichiro, Mifune Yuto, Tanabe Nobutake, Takahashi Takashi

    Synlett   Vol. 25 ( 15 ) page: 2087-2092   2014

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  43. Rapid and Structurally Diverse Synthesis of Multi-Substituted beta-Keto Amide Derivatives Based on a Dioxinone Scaffold Reviewed

    Fuse Shinichiro, Yoshida Hayato, Oosumi Kazuya, Takahashi Takashi

    European Journal of Organic Chemistry   ( 22 ) page: 4854-4860   2014

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  44. Rapid Library Synthesis of Amphiphiles Based On a Dioxinone Scaffold and Identification of Nonlamellar Liquid Crystals Reviewed

    Fuse Shinichiro, Nakamura Kentarou, Mifune Yuto, Marubayashi Hironori, Hijikuro Ichiro, Nojima Shuichi, Tanaka Hiroshi, Takahashi Takashi

    Synlett   Vol. 25 ( 19 ) page: 2806-2813   2014

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  45. Synthesis of EDOT-containing organic dyes via one-pot, four-component Suzuki-Miyaura coupling and the evaluation of their photovoltaic properties Reviewed

    Fuse Shinichiro, Asai Yuya, Sugiyama Sakae, Matsumura Keisuke, Maitani Masato M, Wada Yuji, Ogomi Yuhei, Hayase Shuzi, Kaiho Tatsuo, Takahashi Takashi

    Tetrahedron   Vol. 70 ( 45 ) page: 8690-8695   2014

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  46. Synthesis of N-Allyloxycarbonyl 3,5-Dihydroxyphenylglycine via Photochemical Wolff Rearrangement-Nucleophilic Addition Sequence in a Micro-Flow Reactor Reviewed

    Mifune Yuto, Fuse Shinichiro, Tanaka Hiroshi

    Journal of Flow Chemistry   Vol. 4 ( 4 ) page: 173-179   2014

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  47. Micro-flow synthesis and structural analysis of sterically crowded diimine ligands with five aryl rings Reviewed

    Fuse Shinichiro, Tanabe Nobutake, Tannna Akio, Konishi Yohei, Takahashi Takashi

    Beilstein Journal of Organic Chemistry   Vol. 9   page: 2336-2343   2013

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  48. Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A Reviewed

    Fuse Shinichiro, Inaba Kennichi, Takagi Motoki, Tanaka Masahiro, Hirokawa Takatsugu, Johmoto Kohei, Uekusa Hidehiro, Shin-Ya Kazuo, Takahashi Takashi, Doi Takayuki

    European Journal of Medicinal Chemistry   Vol. 66   page: 180-184   2013

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  49. Sequential Coupling Approach to the Synthesis of Nickel(II) Complexes with N-aryl-2-amino Phenolates Reviewed

    Fuse Shinichiro, Tago Hiroaki, Maitani Masato M, Wada Yuji, Takahashi Takashi

    Acs Combinatorial Science   Vol. 14 ( 10 ) page: 545-550   2012

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  50. An iterative approach to the synthesis of thiophene-based organic dyes Reviewed

    Fuse Shinichiro, Yoshida Hayato, Takahashi Takashi

    Tetrahedron Letters   Vol. 53 ( 26 ) page: 3288-3291   2012

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  51. Combinatorial Synthesis and Evaluation of alpha-Iminocarboxamide-Nickel(II) Catalysts for the Copolymerization of Ethylene and a Polar Monomer Reviewed

    Fuse Shinichiro, Masui Hisashi, Tannna Akio, Shimizu Fumihiko, Takahashi Takashi

    Acs Combinatorial Science   Vol. 14 ( 1 ) page: 17-24   2012

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  52. Continuous-flow synthesis of activated vitamin D-3 and its analogues Reviewed

    Fuse Shinichiro, Mifune Yuto, Tanabe Nobutake, Takahashi Takashi

    Organic & Biomolecular Chemistry   Vol. 10 ( 27 ) page: 5205-5211   2012

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  53. One-Pot, Three-Component Coupling Approach to the Synthesis of alpha-Iminocarboxamides Reviewed

    Masui Hisashi, Fuse Shinichiro, Takahashi Takashi

    Organic Letters   Vol. 14 ( 16 ) page: 4090-4093   2012

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  54. Total synthesis of spiruchostatin B aided by an automated synthesizer Reviewed

    Fuse Shinichiro, Okada Kumiko, Iijima Yusuke, Munakata Asami, Machida Kazuhiro, Takahashi Takashi, Takagi Motoki, Shin-ya Kazuo, Doi Takayuki

    Organic & Biomolecular Chemistry   Vol. 9 ( 10 ) page: 3825-3833   2011

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  55. Continuous in situ generation and reaction of phosgene in a microflow system Reviewed

    Fuse Shinichiro, Tanabe Nobutake, Takahashi Takashi

    Chemical Communications   Vol. 47 ( 47 ) page: 12661-12663   2011

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  56. JBIR-56 and JBIR-57, 2(1H)-Pyrazinones from a Marine Sponge-Derived Streptomyces sp SpD081030SC-03 Reviewed

    Motohashi Keiichiro, Inaba Kennichi, Fuse Shinichiro, Doi Takayuki, Izumikawa Miho, Khan Shams Tabrez, Takagi Motoki, Takahashi Takashi, Shin-ya Kazuo

    Journal of Natural Products   Vol. 74 ( 7 ) page: 1630-1635   2011

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  57. Ribosomal Synthesis of Backbone-Macrocyclic Peptides Containing gamma-Amino Acids Reviewed

    Ohshiro Yukinori, Nakajima Eiji, Goto Yuki, Fuse Shinichiro, Takahashi Takashi, Doi Takayuki, Suga Hiroaki

    Chembiochem   Vol. 12 ( 8 ) page: 1183-1187   2011

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  58. Three-component coupling approach toward the synthesis of a resorcylic acid lactone framework Reviewed

    Sugiyama Sakae, Fuse Shinichiro, Takahashi Takashi

    Tetrahedron   Vol. 67 ( 35 ) page: 6654-6658   2011

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  59. Rapid Assembly of Resorcylic Acid Lactone Frameworks through Sequential Palladium-Catalyzed Coupling Reactions Reviewed

    Fuse Shinichiro, Sugiyama Sakae, Takahashi Takashi

    Chemistry-an Asian Journal   Vol. 5 ( 12 ) page: 2459-2462   2010

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  60. Design, synthesis and evaluation and QSAR analysis of (-)-N 1-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors

    Jun Takahashi, Ichiro Hijikuro, Takeshi Kihara, Modachur G. Murugesh, Shinichiro Fuse, Yoshinori Tsumura, Akinori Akaike, Tetsuhiro Niidome, Takashi Takahashi, Hachiro Sugimoto

    Bioorganic and Medicinal Chemistry Letters   Vol. 20 ( 5 ) page: 1718-1720   2010

  61. Design, synthesis and evaluation of carbamate-modified (-)-N 1-phenetylnorphysostigmine derivatives as selective butyrylcholinesterase inhibitors

    Jun Takahashi, Ichiro Hijikuro, Takeshi Kihara, Modachur G. Murugesh, Shinichiro Fuse, Yoshinori Tsumura, Akinori Akaike, Tetsuhiro Niidome, Takashi Takahashi, Hachiro Sugimoto

    Bioorganic and Medicinal Chemistry Letters   Vol. 20 ( 5 ) page: 1721-1723   2010

  62. Functional and Structural Analysis of a Key Region of the Cell Wall Inhibitor Moenomycin.

    Shinichiro Fuse, Hirokazu Tsukamoto, Yanqiu Yuan, Tsung-Shing Andrew Wang, Yi Zhang, Megan Bolla, Suzanne Walker, Piotr Sliz, Daniel Kahne

    ACS Chemical Biology   Vol. 5 ( 7 ) page: 701-711   2010

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  63. Synthesis of Bicyclic Enediynes That Possess a Photosensitive Triggering Device and Exhibit Strong DNA Cleaving Activity

    Hiroshi Tanaka, Yoshikazu Tanaka, Masafumi Minoshima, Sho Yamaguchi, Shinichiro Fuse, Takayuki Doi, Susumu Kawauchi, Hiroshi Sugiyama and Takashi Takahashi

    Chemical Communications   Vol. 46 ( 32 ) page: 5942-5944   2010

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  64. Construction of the ABC Ring System of Taxanes via Stereoselective One-Pot Three-Component Coupling and Intramolecular Alkylation of a Protected Cyanohydrin Ether

    Takayuki Serizawa, Shigeru Miyamoto, Shinichiro Fuse, Takayuki Doi, and Takashi Takahashi

    Bulletin of the Chemical Society of Japan   Vol. 83 ( 8 ) page: 942-949   2010

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  65. Anti-Influenza Virus Compound from Streptomyces sp RI18 Reviewed

    Takagi Motoki, Motohashi Keiichiro, Nagai Aya, Izumikawa Miho, Tanaka Masahiro, Fuse Shinichiro, Doi Takayuki, Iwase Keiichiro, Kawaguchi Atsushi, Nagata Kyosuke, Takahashi Takashi, Shin-ya Kazuo

    Organic Letters   Vol. 12 ( 20 ) page: 4664-4666   2010

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  66. Continuous-flow synthesis of vitamin D-3 Reviewed

    Fuse Shinichiro, Tanabe Nobutake, Yoshida Masahito, Yoshida Hayato, Doi Takayuki, Takahashi Takashi

    Chemical Communications   Vol. 46 ( 46 ) page: 8722-8724   2010

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  67. Development and Application of a Solution-Phase Automated Synthesizer, 'ChemKonzert' Reviewed

    Machida Kazuhiro, Hirose Yoichiro, Fuse Shinichiro, Sugawara Tohru, Takahashi Takashi

    Chemical & Pharmaceutical Bulletin   Vol. 58 ( 1 ) page: 87-93   2010

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  68. An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked

    Yoshikazu Tanaka, Shinichiro Fuse, Hiroshi Tanaka, Takayuki Doi, Takashi Takahashi

    Organic Process Research & Development   Vol. 13 ( 6 ) page: 1111-1121   2009

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  69. Stereoselective one-pot three-component coupling approach towards the synthesis of the AC ring system of taxanes

    Takayuki Serizawa, Yoshitaka Numajiri, Shinichiro Fuse, Takayuki Doi, Takashi Takahashi

    Tetrahedron Letters   Vol. 50 ( 26 ) page: 3408-3410   2009

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  70. Complete Characterization of the Seventeen Step Moenomycin Biosynthetic Pathway

    Bohdan Ostash, Emma H. Doud, Cecilie Lin, Iryna Ostash, Deborah L. Perlstein, Shinichiro Fuse, Manuel Wolpert, Daniel Kahne, Suzanne Walker

    Biochemistry   Vol. 48 ( 37 ) page: 8830-8841   2009

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  71. Structural analysis of the contacts anchoring moenomycin to peptidoglycan glycosyltransferases and inplications for antibiotic design

    Yanqiu Yuan, Shinichiro Fuse, Bohdan Ostash, Piotr Sliz, Daniel Kahne, Suzanne Walker

    ACS Chemical Biology   Vol. 3 ( 7 ) page: 429   2008

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  72. A formal total synthesis of taxol aided by an automated synthesizer

    Takayuki Doi, Shinichiro Fuse, Shigeru Miyamoto, Kazuoki Nakai, Daisuke Sasuga, Takashi Takahashi

    Chemistry an Asian Journal   Vol. 1 ( 3 ) page: 370-383   2006

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  73. Ti(III) catalyzed radical cyclization of 6, 7-epoxygeranyl acetate

    Shinichiro Fuse, Malcoln Hanochi, Takashi Takahashi, Takayuki Doi

    Tetrahedron letters   Vol. 45 ( 9 ) page: 1961-1963   2004

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▼display all

Presentations 151

  1. 古典的反応剤を駆使する新規フロー反応の開発を目指して Invited

    布施新一郎

    第15回プロセス化学ラウンジ  2024.12.5 

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    Event date: 2024.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:浜名湖弁天島リゾート THE OCEAN、静岡   Country:Japan  

  2. 化学における知識発見を加速する対話エージェント

    三輪 拓真、平澤 寅庄、吉野 幸一郎、馬場 雪乃、藤吉 弘亘、坂口 慶祐、 松原 誠二郎、宮尾 知幸、椴山 儀恵、布施 新一郎、小野 寛太、牛久 祥孝

    第15回対話システムシンポジウム(第102回SLUD研究会)  2024.11.29 

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    Event date: 2024.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:国立国語研究所、東京  

  3. Microflow synthesis of peptides Invited International conference

    Shinichiro Fuse

    2024 BrainLink X-Lab Day  2024.11.23 

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    Event date: 2024.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Grand Josun Busan Hotels & Resorts, Busan, Korea  

  4. 古典的反応剤による新輝不老反応の開発をめざして Invited

    布施新一郎

    第47回ケムステVシンポ「マイクロフローケミストリー」  2024.11.13 

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    Event date: 2024.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  5. Developing new microflow processes using classical reagents Invited International conference

    Shinichiro Fuse

    Flow Chemistry Asia 2024 

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    Event date: 2024.11

    Language:English   Presentation type:Oral presentation (keynote)  

    Venue:Hotel Nikko Narita, Ibaraki, Japan   Country:Japan  

  6. Microflow Synthesis of C-Terminal-Free Sterically Hindered Specialty Peptides International conference

    Hinata Dosaki, Ting-Ho Chen, Shinichiro Fuse

    The 61st Japanese Peptide Symposium  2024.10.29 

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    Event date: 2024.10

    Language:English   Presentation type:Poster presentation  

    Venue:Nagoya University, Nagoya, Aichi, Japan   Country:Japan  

  7. Switchable Acylation of H-Phosphonate with Acyl Ammonium/Pyridinium Ion in a Micro-Flow Reactor International conference

    Hiroshi Kitamura, Yuma Tanaka, Shinichiro Fuse

    International Microreaction Technology Conference (IMRET17)  2024.10.28 

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    Event date: 2024.10

    Language:English   Presentation type:Oral presentation (general)  

  8. Micro-Flow Synthesis of Unsymmetrical H-Phosphonates and Consideration of a Mechanism for Reduced Overreaction International conference

    Yuma Tanaka・Hiroshi Kitamura・Shinichiro Fuse

    International Microreaction Technology Conference (IMRET17)  2024.10.28 

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    Event date: 2024.10

    Language:English   Presentation type:Oral presentation (general)  

  9. 高求電子性活性種を利用するマイクロフロー合成法

    山崎直人, 布施新一郎

    文部科学省科学研究費助成事業「学術変革領域A:デジタル化による高度精密有機合成の新展開」第6回成果報告会  2024.9.5 

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    Event date: 2024.9

    Language:Japanese   Presentation type:Poster presentation  

    Venue:横浜国立大学常盤台キャンパス   Country:Japan  

  10. Microflow synthesis of peptides Invited International conference

    Shinichiro Fuse

    The 18th Chinese International Peptide Symposium (CPS2024)  2024.6.30 

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    Event date: 2024.6 - 2024.7

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hong Kong Ocean Park Marriott Hotel, Hong Kong, China  

  11. マイクロフローリアクター内での三塩化リンに対する連続的な直接アルコキシ化による非対称H―ホスホネートの合成

    田中 裕真、北村 宙士、布施 新一郎

    第124回有機合成シンポジウム  2024.6.27 

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    Event date: 2024.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:北海道大学鈴木章ホール   Country:Japan  

  12. 二残基ずつペプチド鎖を伸長できる超高速マイクロフロー合成法による医薬品候補化合物の創出 Invited

    布施新一郎

    JBA未来へのバイオ技術勉強会, 超高速革新的大量薬剤生産  2024.5.10 

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    Event date: 2024.5

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:web講演   Country:Japan  

  13. 非対称H-ホスホネートのマイクロフロー合成法の開発と反応の詳細に関する考察

    田中 裕真、北村 宙士、布施 新一郎

    日本化学会第104春季年会  2024.3.20 

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学船橋キャンパス 千葉   Country:Japan  

  14. Chemo-selective acylation of H-phosphonate with acyl ammonium/pyridinium ion in a micro-flow reactor International coauthorship

    Hiroshi Kitamura, Shinichiro Fuse

    2024.3.20 

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    Event date: 2024.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  15. Development of rapid peptide chain elongation via a three-component coupling approach International coauthorship

    Naoto Sugisawa, Akira Ando, Shinichiro Fuse

    2024.3.20 

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    Event date: 2024.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  16. マイクロフロー合成法を駆使したトリフルオロメタンスルホン酸によるカルボカチオン生成と続く求核付加反応の開発

    松浦 祐真、布施 新一郎

    日本化学会第104春季年会  2024.3.20 

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学船橋キャンパス 千葉   Country:Japan  

  17. マイクロフローリアクターを用いたt-ブチルオキシクロリドおよびその等価体の迅速合成と利用法開発

    宮本 佳奈、岡部 蓮、布施 新一郎

    日本化学会第104春季年会  2024.3.20 

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学船橋キャンパス 千葉   Country:Japan  

  18. マイクロフローリアクターを用いたペプトイド合成におけるジケトピペラジン形成の回避

    大倉 優輝、田中 裕真、布施 新一郎

    日本化学会第104春季年会  2024.3.20 

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学船橋キャンパス 千葉   Country:Japan  

  19. フロー・自動合成、機械学習技術が駆動する有機合成の革新 Invited

    布施新一郎

    第8回FlowSTシンポジウム  2024.2.9 

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    Event date: 2024.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:イイノホール、東京   Country:Japan  

  20. 新輝不老反応の開発を目指して Invited

    布施新一郎

    東海コンファレンス2023 in 岡崎  2024.1.10 

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    Event date: 2024.1

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:岡崎コンファレンスセンター、愛知   Country:Japan  

  21. 古典的な新輝不老反応の開発を目指して Invited

    布施新一郎

    化学プロセス研究コンソーシアム2023年度第2回全体会議  2023.12.18 

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    Event date: 2023.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:京都大学桂キャンパス、京都   Country:Japan  

  22. ベイズ最適化による研究・開発効率化検討

    百瀬一樹, 杉澤宏樹, 田邊祐介, 堀田一海, 白鳥和矢, 宮澤朋久, 藤谷忠博, 杉澤直斗, 中林晃平, 布施新一郎

    第46回ケモインフォマティクス討論会  2023.11.23  日本化学会 ケモインフォマティクス部会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:中央大学、東京   Country:Japan  

  23. フロー・自動合成、機械学習技術が駆動する有機合成の革新 Invited

    布施新一郎

    第37回農薬デザイン研究会  2023.11.22 

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    Event date: 2023.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:ホテルマイステイズ新大阪コンファレンスセンター、大阪   Country:Japan  

  24. マイクロフローリアクター中でのカップリング-環化連続反応による環状リン酸トリエステルの高速合成

    中林 晃平、北村 宙士、布施 新一郎

    第40回メディシナルケミストリーシンポジウム  2023.11.13  日本薬学会 医薬化学部会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:名古屋大学 愛知   Country:Japan  

  25. 三塩化リンに対する直接アルコキシ化を用いた非対称H-ホスホネートのマイクロフロー合成法の開発

    田中 裕真、北村 宙士、布施 新一郎

    第40回メディシナルケミストリーシンポジウム  2023.11.13  日本薬学会 医薬化学部会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:名古屋大学 愛知   Country:Japan  

  26. マイクロフロー合成法を駆使するフラン環隣接炭素上での迅速求核置換反応の開発

    松浦 祐真、増井 悠、布施 新一郎

    第40回メディシナルケミストリーシンポジウム  2023.11.13  日本薬学会 医薬化学部会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:名古屋大学 愛知   Country:Japan  

  27. マイクロフローリアクター中でのアシルアンモニウムイオンによるH-ホスホネートの化学選択的アシル化反応の開発

    北村 宙士、布施 新一郎

    第123回有機合成シンポジウム  2023.11.7  有機合成化学協会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:早稲田大学国際会議場、東京   Country:Japan  

  28. マイクロフローリアクター中でのアシルアンモニウムイオンによるH-ホスホネートの化学選択的アシル化反応の開発

    北村 宙士、布施 新一郎

    第123回有機合成シンポジウム  2023.11.7  有機合成化学協会

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    Event date: 2023.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:早稲田大学国際会議場、東京   Country:Japan  

  29. マイクロフローを駆使する連続的迅速活性種スイッチング法の開発

    宮本 佳奈、岡部 蓮、布施 新一郎

    第13回CSJ化学フェスタ   2023.10.18  日本化学会

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    Event date: 2023.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:タワーホール船堀、千葉   Country:Japan  

  30. Rapid and column-chromatography-free flow-peptide chain elongation Invited International conference

    Shinichiro Fuse

    Flow Chemistry Asia 2023 

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    Event date: 2023.10

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hotel Nikko Narita, Ibaraki, Japan   Country:Japan  

  31. マイクロフロー合成法を駆使する超高効率ペプチド合成手法の開発 Invited

    布施新一郎

    富山県立大学生物・医薬品工学研究センターセミナー 医薬品製造のDx 第一回 セミナー  2023.8.30 

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    Event date: 2023.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:富山県立大学、富山   Country:Japan  

  32. 非対称H-ホスホネートのマイクロフロー合成法と反応の詳細に関する考察

    田中裕真、北村宙士、布施新一郎

    第69回日本薬学会東海支部大会  2023.7.8 

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    Event date: 2023.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:名古屋大学 愛知   Country:Japan  

  33. ペプチドの超高速マイクロフロー合成

    布施新一郎

    ITbM/GTRコンソーシアム第11回ワークショップ  2023.7.4 

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    Event date: 2023.7

    Language:Japanese   Presentation type:Symposium, workshop panel (nominated)  

    Venue:名古屋大学、愛知   Country:Japan  

  34. 古典的な新輝不老反応の開発を目指して Invited

    布施新一郎

    第56回天然物化学談話会  2023.6.29  天然物化学談話会世話人会

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    Event date: 2023.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:つくば国際会議場、茨城   Country:Japan  

  35. Innovation of organic synthesis driven by machine-learning, automated synthesis, and micro-flow synthesis International conference

    Shinichiro Fuse

    2023.4.4  Imperial College London ROAR

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    Event date: 2023.4

    Language:English   Presentation type:Public lecture, seminar, tutorial, course, or other speech  

    Venue:Imperial College London, Molecular Sciences Research Hub, London, UK   Country:United Kingdom  

  36. 多環一挙構築法によるヘテロ原子含有フェネストランの効率的合成とその構造解析

    増井悠、石川裕貴、布施新一郎、高橋孝志

    日本薬学会第143春季年会  2023.3.26 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:北海道大学 北海道   Country:Japan  

  37. マイクロフロー法によるフラン類縁体のα位での迅速求核置換反応の開発

    松浦祐真、増井悠、布施新一郎

    日本化学会第103春季年会  2023.3.22 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス 千葉   Country:Japan  

  38. Investigation into the effect of tertiary amine and Brønsted acid for rapid formation and amidation of mixed anhydride using a micro-flow reactor International coauthorship

    Ting-Ho Chen, Otoka Shamoto, Shinichiro Fuse

    2023.3.22 

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    Event date: 2023.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  39. 非対称H-ホスホネートのマイクロフロー合成法の開発

    田中裕真、北村宙士、布施新一郎

    日本化学会第103春季年会 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス 千葉   Country:Japan  

  40. マイクロフローリアクター中でのカップリング-環化連続反応による環状リン酸トリエステルの高速合成

    中林晃平、北村宙士、布施新一郎

    日本化学会第103春季年会  2023.3.22 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス 千葉   Country:Japan  

  41. Highly efficient peptide chain elongation via one-flow, three-component coupling approach Invited International conference

    Shinichiro Fuse

    11th Singapore International Chemistry Conference (SICC-11)  2022.12.14 

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    Event date: 2022.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Innovis Building, Singapore   Country:Singapore  

  42. Micro-flow synthesis of asymmetrical phosphotriesters and its mechanistic consideration using DFT calculation International conference

    Hiroshi Kitamura, Yuma Otake, Naoto Sugisawa, Hiroki Sugisawa, Tomonori Ida, Hiroyuki Nakamura, Shinichiro Fuse

    International Microreaction Technology Conference (IMRET16)  2022.11.29 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (general)  

  43. Rapid, mild and column-free peptide chain elongation via one-flow, three-component coupling approach International conference

    Naoto Sugisawa, Akira Ando, Shinichiro Fuse

    International Microreaction Technology Conference (IMRET16)  2022.11.28 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (general)  

  44. Micro-flow synthesis of peptide International conference

    Shinichiro Fuse

    International Microreaction Technology Conference (IMRET16)  2022.11.28 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (general)  

  45. 古くて新しい高求電子性反応剤を用いるマイクロフロー合成法の開発 Invited

    布施 新一郎

    第39回メディシナルケミストリーシンポジウム  2022.11.25  日本薬学会医薬化学部会

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    Event date: 2022.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  46. 連続的多成分連結反応を基盤とするペプチド鎖高速伸長法の開発

    杉澤 直斗、安東 章、岡部 蓮、布施 新一郎

    第121回有機合成シンポジウム  2022.11.8  有機合成化学協会

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    Event date: 2022.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:早稲田大学国際会議場、東京   Country:Japan  

  47. 連続的多成分連結反応を基盤とするペプチド鎖高速伸長法の開発

    杉澤 直斗、安東 章、岡部 蓮、布施 新一郎

    第121回有機合成シンポジウム  2022.11.8  有機合成化学協会

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    Event date: 2022.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:早稲田大学国際会議場、東京   Country:Japan  

  48. The Past, Present, and Future of Automation in Synthetic Organic Chemistry Invited International conference

    Shinichiro Fuse

    Nobel Turing Challenge Initiative (NTCI): The 2nd Workshop on Nobel Turing Challenge  2022.11.1 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Nobel Turing Challenge Initiative (NTCI)   Country:Japan  

  49. Rapid, mild, and column-free peptide chain elongation via one-flow, three-component coupling approach International conference

    Naoto Sugisawa, Akira Ando, Shinichiro Fuse

    The 59th Japanese Peptide Symposium  2022.10.26 

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    Event date: 2022.10

    Language:English   Presentation type:Oral presentation (general)  

    Venue:TAHKNET Hall Sendai, Miyagi, Japan   Country:Japan  

  50. Micro-flow synthesis of peptides International conference

    Shinichiro Fuse

    The 59th Japanese Peptide Symposium  2022.10.26 

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    Event date: 2022.10

    Language:English   Presentation type:Poster presentation  

    Venue:TAHKNET Hall Sendai, Miyagi, Japan   Country:Japan  

  51. マイクロフローリアクター内での迅速な両基質活性化を駆使したウレタン保護 α アミノ酸 N-カルボン酸無水物の合成

    岡部 蓮、杉澤 直斗、布施 新一郎

    第12回CSJ化学フェスタ   2022.10.20  日本化学会

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    Event date: 2022.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  52. マイクロフロー技術の活用によるジアリールメタノールの迅速求核置換反応の開発

    松浦 祐真、神田 瀬奈、増井 悠、布施 新一郎

    第12回CSJ化学フェスタ   2022.10.19  日本化学会

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    Event date: 2022.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  53. 鎖状分子からの多環構築を基盤としたフェネストラン類の効率的合成法の確立

    石川 裕貴、増井 悠、布施 新一郎、高橋 孝志

    第12回CSJ化学フェスタ   2022.10.20  日本化学会

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    Event date: 2022.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  54. Micro-Flow Synthesis of Specialty Peptides Invited International conference

    Shinichiro Fuse

    Flow Chemistry Asia 2022 

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    Event date: 2022.10

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hotel Nikko Narita, Ibaraki, Japan   Country:Japan  

  55. フロー化学を通じた古典的活性種の理解と応用 Invited

    布施新一郎

    第38回有機合成化学セミナー  2022.9.28  有機合成化学協会

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    Event date: 2022.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:アクティブリゾーツ福岡八幡、福岡   Country:Japan  

  56. フロー・自動合成、機械学習技術が駆動する創薬の革新

    布施新一郎

    令和4年度生命科学・創薬研究支援基盤事業BINDSシンポジウム  2022.8.24 

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    Event date: 2022.8

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:一橋講堂 東京   Country:Japan  

  57. 分子内ダブル[3+2]環化付加反応によるフェネストランの一挙構築法開発

    石川裕貴、増井悠、布施新一郎、高橋孝志

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  58. ペプチドの連続合成を目的とした装置開発研究

    足立恭平、小竹佑磨、社本泰樹、小川潤一、岩永なつみ、山下義明、小林豊、桝屋圭一、布施新一郎、伊藤篤志、久保大輔

    日本プロセス化学会2022サマーシンポジウム  2022.6.30  日本プロセス化学会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:富山県民会館、富山   Country:Japan  

  59. マイクロフローリアクター内での環状ペプチド合成法の開発

    社本乙華、小室敬史、杉澤直斗、中村浩之、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  60. マイクロフローリアクターを用いた瞬間希釈による環状リン酸トリエステルの高速合成

    中林晃平、北村宙士、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  61. マイクロフローリアクター内での迅速な両器質同時活性化を駆使したウレタン保護アミノ酸N-カルボン酸無水物の合成

    岡部蓮、杉澤直斗、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  62. マイクロフロー合成法を用いたインドール類縁体のα位炭素上での迅速求核置換反応の開発

    神田瀬奈、増井悠、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  63. 連続多成分連結反応を基盤とするペプチド鎖高速伸長法の開発

    杉澤直斗、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  64. 非対称リン酸トリエステルのマイクロフロー合成および反応機構解明

    北村宙士、小竹佑磨、杉澤直斗、杉澤宏樹、井田朋智、中村浩之、布施新一郎

    創薬懇話会2022 in 名古屋 (Webポスター発表)  2022.7.1  日本薬学会 医薬化学部会

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    Event date: 2022.6 - 2022.7

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  65. 非対称リン酸トリエステルのマイクロフロー合成および反応機構解明

    北村宙士、小竹佑磨、杉澤直斗、杉澤宏樹、井田朋智、中村浩之、布施新一郎

    第120回有機合成シンポジウム  2022.6.28  有機合成化学協会

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    Event date: 2022.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:web開催   Country:Japan  

  66. 機械学習を利用するマイクロフロー合成法開発 Invited

    布施新一郎

    近畿化学協会合成部会令和4年度第 1回合成フォーラム  2022.6.10 

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    Event date: 2022.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:大阪科学技術センター, 大阪   Country:Japan  

  67. マイクロフロー合成法が駆動する特殊ペプチド創薬の革新 Invited

    布施 新一郎

    日本薬学会第142年会   2022.3.28 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  68. マイクロフロー合成法を用いた電子過剰系芳香環α位の求核置換反応の開発

    増井 悠、神田 瀬奈、松浦 祐真、布施 新一郎

    日本薬学会第142年会   2022.3.28 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  69. 分子内ダブル[3+2]環化付加反応によるスピロ環含有多環式化合物の一挙構築法開発

    石川 裕貴、増井 悠、布施 新一郎、高橋 孝志

    日本化学会第102春季年会   2022.3.24 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  70. マイクロフローリアクター内での環状ペプチド合成法の開発

    社本 乙華、小室 敬史、杉澤 直斗、中村 浩之、布施 新一郎

    日本化学会第102春季年会   2022.3.23 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  71. マイクロフロー合成法を用いたインドール類縁体のα位炭素上での迅速求核置換反応の開発

    神田 瀬奈、増井 悠、布施 新一郎

    日本化学会第102春季年会   2022.3.23 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  72. マイクロフローリアクター内での迅速な両基質同時活性化を駆使した ウレタン保護-N-カルボン酸無水物の合成

    岡部 蓮、杉澤 直斗、布施 新一郎

    日本化学会第102春季年会   2022.3.23 

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    Event date: 2022.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  73. Highly efficient amide bond formation using micro-flow technology Invited International conference

    Shinichiro Fuse

    2021 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2021)  2021.12.18 

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    Event date: 2021.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Web presentation  

  74. Micro-flow synthesis of β-amino acid N-carboxy anhydrides and β-amino acid derivatives via pH flash switching and rapid dual activation International conference

    Naoto Sugisawa, Yuma Otake, Hiroyuki Nakamura, Shinichiro Fuse

    2021 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2021)  2021.12.19 

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    Event date: 2021.12

    Language:English   Presentation type:Poster presentation  

    Venue:Web presentation  

  75. フロー・自動合成・機械学習を駆使する有機合成 Invited

    布施新一郎

    第35回岡山マイクロリアクターネット例会  2021.12.4 

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    Event date: 2021.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:岡山国際交流センター、岡山   Country:Japan  

  76. 非対称リン酸トリエステルのマイクロフロー合成および反応機構解明

    北村宙士、小竹佑磨、杉澤直斗、杉澤宏樹、井田朋智、中村浩之、布施新一郎

    第11回CSJ化学フェスタ   2021.10.20  日本化学会

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    Event date: 2021.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  77. ベイズ最適化を駆使した非対称スルファミドの迅速かつ温和なワンフロー合成法の開発 International coauthorship

    杉澤 直斗、杉澤宏樹、小竹佑磨、Roman V. Krems、中村浩之、布施新一郎

    第11回CSJ化学フェスタ   2021.10.21  日本化学会

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    Event date: 2021.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:web開催   Country:Japan  

  78. ベイズ最適化を用いた非対称スルファミドの迅速かつ温和なワンフロー合成法の開発 International coauthorship

    杉澤 直斗、杉澤宏樹、小竹佑磨、Roman V. Krems、中村浩之、布施新一郎

    第11回CSJ化学フェスタ   2021.10.20  日本化学会

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    Event date: 2021.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:web開催   Country:Japan  

  79. マイクロフローペプチド合成の最近の成果と反応開発における機械学習の利用法の提案 Invited

    布施新一郎

    近畿化学協会フロー・マイクロ合成研究会第88回研究会  2021.8.6 

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    Event date: 2021.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  80. フロー・自動合成・機械学習を駆使する有機合成の未来 Invited

    布施新一郎

    第33回万有札幌シンポジウム 有機化学~その無限の可能性の追求  2021.6.26 

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    Event date: 2021.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:web講演   Country:Japan  

  81. ベイズ最適化を駆使した非対称スルファミドのワンフロー合成法の開発 International coauthorship

    杉澤 直斗、杉澤宏樹、小竹佑磨、Roman V. Krems、中村浩之、布施新一郎

    日本プロセス化学会2021サマーシンポジウム  2021.6.24 

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    Event date: 2021.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  82. Development of a one-flow synthetic approach to the unsymmetrical sulfamides utilizing Bayesian optimization International coauthorship International conference

    Naoto Sugisawa, Hiroki Sugisawa, Yuma Otake, Roman. V. Krems, Hiroyuki Nakamura, Shinichiro Fuse

    ACS Publications Symposium The Power of Chemical Transformations  2021.5.20 

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    Event date: 2021.5

    Language:English   Presentation type:Poster presentation  

    Country:China  

  83. ジアルケニルアミンのヒドロホルミル化とピロリジジンアルカロイドの合成への応用 Invited

    増井 悠、新津 さくら、庄司 満、布施 新一郎、高橋 孝志

    日本薬学会第141春季年会   2021.3.28 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Poster presentation  

    Venue:Web講演   Country:Japan  

  84. マイクロフロー・自動合成技術が駆動する創薬の革新 Invited

    布施新一郎

    日本化学工学会第86年会  2021.3.21 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:web講演   Country:Japan  

  85. マイクロフローリアクター内での瞬間両基質活性化を駆使したβ-アミノ酸誘導体の合成

    杉澤 直斗、中村 浩之、布施 新一郎

    日本化学会第101春季年会   2021.3.20 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  86. マイクロフローリアクター内でのトリホスゲンを用いた迅速なラクタム合成法の開発

    小室 敬史、小竹 佑磨、中村 浩之、布施 新一郎

    日本化学会第101春季年会   2021.3.22 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  87. フロー・自動合成技術が駆動する創薬の革新 Invited

    布施新一郎

    日本化学会第101春季年会  2021.3.20 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:web講演   Country:Japan  

  88. マイクロフローリアクターを用いる非対称リン酸トリエステルの高速合成

    北村宙士、小竹佑磨、中村浩之、布施新一郎

    日本化学会第101春季年会   2021.3.20 

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:Web講演   Country:Japan  

  89. マイクロフローアミド結合形成法が駆動する創薬の革新 Invited

    布施新一郎

    Kanazawa University University Sakigake Project 2020 Seminar 3rd Ohmiya Lab and Takeda Virtual Symposium 

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    Event date: 2021.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  90. マイクロフロー合成法を駆使する古くて新しい有機合成法の開発 Invited

    布施新一郎

    有機合成化学協会東海支部主催 令和2年度有機合成セミナー 

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    Event date: 2020.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  91. マイクロフロー合成、自動合成による医薬品生産の革新 Invited

    布施新一郎

    化学工学会関東支部第52回Continuing Educationシリーズ講習会「医薬品原薬のフロー合成」-1日でわかるフロー合成の要素技術からシステム・情報まで- 

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    Event date: 2020.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  92. 創薬研究の自動化の動向と「いったい今後はどうなるのか?」問題 Invited

    布施新一郎

    武田薬品プロセスケミストリーデベロップメントシンポジウム 

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    Event date: 2020.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  93. 有機合成の自動化・遠隔化の波とフロー合成の今後 Invited

    布施新一郎

    近畿化学協会フロー・マイクロ合成研究会第88回研究会 

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    Event date: 2020.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  94. マイクロフロー合成と自動合成が導く創薬の革新 Invited

    布施新一郎

    CBI学会2020大会 

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    Event date: 2020.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  95. Development of amide bond formation via mixed carbonic anhydride in a micro-flow reactor Invited

    Shinichiro Fuse

    6th International Symposium on Middle Molecular Strategy (ISMMS-6) 

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    Event date: 2020.10

    Language:English   Presentation type:Oral presentation (invited, special)  

    Country:Japan  

  96. 自動化はどこからきたのか 自動化は何者か 自動化はどこへ行くのか  ~有機合成の自動化を考える~ Invited

    布施新一郎

    Laboratory Automation Developers Conference (LADEC2020) 

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    Event date: 2020.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  97. コロナで変わる創薬研究 アカデミアからの提言 Invited

    布施新一郎

    第8回中部地区創薬オープンイノベーション情報交換会 

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    Event date: 2020.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  98. マイクロフロー合成、自動合成、AIが駆動する有機合成化学の進展 Invited

    布施新一郎

    日本学術振興会プロセスシステム工学第143委員会研究会 

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    Event date: 2020.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:Web講演   Country:Japan  

  99. 混合炭酸無水物を経由するアミド結合形成法の開発

    布施新一郎

    新学術領域研究反応集積化が導く中分子戦略高次生物機能分子の創製第9回公開成果報告会 

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    Event date: 2020.1

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:大阪大学, 大阪   Country:Japan  

  100. 混合炭酸無水物を経由するアミド結合形成法の開発

    布施新一郎

    新学術領域研究反応集積化が導く中分子戦略高次生物機能分子の創製第9回公開成果報告会 

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    Event date: 2020.1

    Language:Japanese   Presentation type:Poster presentation  

    Venue:大阪大学, 大阪   Country:Japan  

  101. Investigation of amide bond formation based on micro-flow technologies Invited

    Shinichiro Fuse

    Keio International Symposium on Innovative Synthesis of Complex Molecules 

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    Event date: 2019.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Country:Japan  

  102. Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor International conference

    Shinichiro Fuse

    The 18th Asian Chemical Congress and The 20th General Assembly of the Federation of Asia Chemical Societies 

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    Event date: 2019.12

    Language:English   Presentation type:Oral presentation (general)  

    Venue:Taipei International Convention Center, Taipei, Taiwan   Country:Taiwan, Province of China  

  103. マイクロフロー合成法を駆使する古くて新しいアミド結合形成法の開発

    布施新一郎

    GTR seeds seminar 

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    Event date: 2019.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:名古屋大学, 愛知   Country:Japan  

  104. マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新 International conference

    布施新一郎

    資源研設立80年記念シンポジウム 

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    Event date: 2019.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京工業大学, 神奈川   Country:Japan  

  105. Efficient amide bond formation based on micro-flow technology Invited International conference

    Shinichiro Fuse

    Flow Chemistry Asia 2019 

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    Event date: 2019.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hotel Nikko Narita, Ibaraki, Japan   Country:Japan  

  106. Investigation of Amide Bond Formation based on Micro-flow Technologies

    Shinichiro Fuse

    Tateshina Conference on Organic Chemistry 

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    Event date: 2019.11

    Language:English   Presentation type:Poster presentation  

    Venue:Skypark Hotel in Kurumayama Kogen, Nagano   Country:Japan  

  107. 奥深いアミド化の世界へのご招待ーマイクロフロー合成法を道具としてー Invited

    布施新一郎

    第18回化学系若手研究者セミナー 

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    Event date: 2019.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東北大学青葉台キャンパス 宮城   Country:Japan  

  108. Investigation of amide bond formation based on micro-flow technologies Invited

    Shinichiro Fuse

    2nd SMARC Symposium: New Stream of Chemical Biology 

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    Event date: 2019.7

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Chiba University, Chiba Iodine Resource Innovation Center (CIRIC) Chiba Japan   Country:Japan  

  109. 高速マイクロフローアミド結合形成法の開発とペプチド合成の革新 Invited

    布施新一郎

    原薬の連続生産に関する研究開発と規制動向に関するシンポジウム 

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    Event date: 2019.4

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:ソラシティコンフェレンスセンター 東京   Country:Japan  

  110. Innovation of Peptide Synthesisbased on Micro-Flow Technology Invited

    Shinichiro Fuse

    Let's leap! Challenges in Organic Chemistry 

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    Event date: 2019.4

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:The University of Tokyo Tokyo Japan   Country:Japan  

  111. Highly Efficient Amide Bond Formation using Micro-Flow Technology Invited International conference

    Shinichiro Fuse

    Flow Chemistry Europe 2019 

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    Event date: 2019.2

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Wellcome Genome Centre UK   Country:United Kingdom  

  112. マイクロフロー技術を駆使する高収率・省スペースかつ低コストの革新的ペプチド合成法の開発 Invited

    布施新一郎

    日本医療研究開発機構(AMED)平成30年度 創薬基盤推進研究事業 公開シンポジウム 

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    Event date: 2019.1

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:新霞が関ビル 全社協・灘尾ホール 東京   Country:Japan  

  113. Highly Efficient Amide Bond Formation Using Micro-flow Technology Invited International conference

    Shinichiro Fuse

    10th Singapore International Chemistry Conference (SICC-10) 

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    Event date: 2018.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:National University of Singapore Singapore   Country:Singapore  

  114. マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新 Invited

    布施新一郎

    第四回魚住触媒研究会 

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    Event date: 2018.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:分子科学研究所 岡崎カンファレンスセンター 愛知   Country:Japan  

  115. 高速マイクロフローアミド結合形成法の開発とペプチド合成の革新 Invited

    布施新一郎

    新学術領域「中分子戦略」「分子夾雑化学」ジョイントシンポジウム 第21回生命化学研究会 

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    Event date: 2018.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:大阪大学 南部陽一郎ホール 大阪   Country:Japan  

  116. 高速マイクロフローアミド結合形成法の開発とペプチド合成の革新 Invited

    布施新一郎

    日本プロセス化学会2018サマーシンポジウム 

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    Event date: 2018.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:タワーホール船堀 東京   Country:Japan  

  117. マイクロフローリアクターを用いる高速・高効率アシル化反応 Invited

    布施新一郎

    平成30年度 前期(春季)有機合成化学講習会 

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    Event date: 2018.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:日本薬学会長井記念館長井記念ホール 東京   Country:Japan  

  118. マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新 Invited

    布施新一郎

    第15回フッ素相模セミナー 

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    Event date: 2018.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東ソー株式会社東京研究所 神奈川   Country:Japan  

  119. マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新 Invited

    布施新一郎

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:ANA クラウンプラザホテル金沢 石川   Country:Japan  

  120. Highly Efficient Amide Bond Formation Using Micro-flow Technology Invited International conference

    Shinichiro Fuse

    The First International Conference on Automated Flow and Microreactor Synthesis (ICAMS-1) 

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    Event date: 2018.1

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hotel Hankyu EXPO park Osaka Japan   Country:Japan  

  121. マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新 Invited

    布施新一郎

    「有機合成を基盤とした生物活性分子の創製」第1回講演会 

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    Event date: 2017.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:岡山大学 岡山   Country:Japan  

  122. Highly Efficienty Amide Bond Formation Using Micro-flow Technology Invited International conference

    Shinichiro Fuse

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    Event date: 2017.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Embassador International Hotel China   Country:China  

  123. マイクロフロー法を駆使する天然物の高効率合成法の開発 Invited

    布施新一郎

    大塚有機合成シンポジウム2017 

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    Event date: 2017.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:大塚製薬 ヴェガホール 徳島   Country:Japan  

  124. マイクロフローアミド化法を駆使するペプチドの高効率合成 Invited

    布施新一郎

    化学とマイクロ・ナノシステム学会第36回研究会 

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    Event date: 2017.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:桐生市市民文化会館 群馬   Country:Japan  

  125. ペプチドの低コスト生産を志向したマイクロフローアミド結合形成法の開発 Invited

    布施新一郎

    第5回バイオ関連化学シンポジウム若手フォーラム 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東京大学理学系研究科化学講堂 東京   Country:Japan  

  126. 迅速かつ強力なカルボン酸の活性化を基盤とするマイクロフローペプチド合成法の開発 Invited

    布施新一郎

    第34回有機合成化学セミナー 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:金沢文化ホール 石川   Country:Japan  

  127. 超高速マイクロフローアミド化反応の開発とペプチド合成の革新 Invited

    布施新一郎

    千葉大学大学院薬学研究院第11回化学系若手研究者講演会 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:千葉大学亥鼻キャンパス医薬系総合研究棟II地下大会議室 千葉   Country:Japan  

  128. マイクロフロー法を駆使する最強のアミド化法開発を目指して Invited

    布施新一郎

    新学術領域研究「反応集積化が導く中分子戦略:高次生物機能分子の創製」 若手シンポジウム 

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    Event date: 2017.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:秋保リゾートホテルクレセント 宮城   Country:Japan  

  129. 微小流路中での高速アミド化反応(秒単位)を駆使するペプチド合成 Invited

    布施新一郎

    第49回若手ペプチド夏の勉強会 

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    Event date: 2017.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:長崎ブルースカイホテル 長崎   Country:Japan  

  130. マイクロフロー合成を駆使するアミド化法の開発とペプチド合成の革新 Invited

    布施新一郎

    第49回触媒化学融合研究センター講演会 

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    Event date: 2017.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:産業技術総合研究所 茨城   Country:Japan  

  131. Highly Efficient Amide Bond Formation Using Micro-flow Technology Invited International conference

    Shinichiro Fuse

    The International Symposium on Pure & Applied Chemistry (ISPAC) 2017 

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    Event date: 2017.6

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Hotel Continental Saigon Saigon Vietnam   Country:Viet Nam  

  132. マイクロフローペプチド合成法の開発 -奥深いアミド化の世界- Invited

    布施 新一郎

    東工大応用化学系 次世代を担う若手シンポジウム 

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    Event date: 2017.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:慶應義塾大学 神奈川   Country:Japan  

  133. An efficient amide bond formation through rapid and strong activation of carboxylic acids in a micro-flow reactor Invited International conference

    Shinichiro Fuse

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Keio University Kanagawa Japan   Country:Japan  

  134. マイクロフローアミド結合形成法の開発-単純なようで奥深いアミド化の世界- Invited

    布施新一郎

    第11回プロセス化学ラウンジ 

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    Event date: 2016.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:和光純薬工業株式会社 湯河原研修所 神奈川   Country:Japan  

  135. わずか5秒以内でアミノ酸を連結する超高速マイクロフローペプチド合成法の開発 Invited

    布施新一郎

    第6回CSJ化学フェスタ2016 

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    Event date: 2016.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:タワーホール船堀 東京   Country:Japan  

  136. 強力かつ迅速なカルボン酸の活性化を基盤とするマイクロフローペプチド合成法の開発 Invited

    布施新一郎

    2016年度第7回マイクロ化学プロセス分科会主催講演会 

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    Event date: 2016.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:ダイキン工業株式会社 淀川製作所テクノロジー・イノベーションセンター 大阪   Country:Japan  

  137. フロー反応でしか実現できない高効率合成法開発を目指して Invited

    布施新一郎

    電磁波励起反応場第188委員会 平成28年度 第1回化学材料分科会 

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    Event date: 2016.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東京工業大学 蔵前会館 東京   Country:Japan  

  138. Elucidating the structure-property relationship of donor-π-acceptor dyes for DSSCs through rapid library synthesis Invited

    Shinichiro Fuse

    AEARU 6th Energy and Environmental Workshop 

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    Event date: 2016.8

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Tokyo Institute of Technology Tokyo Japan   Country:Japan  

  139. 生物活性天然物のマイクロフロー合成:「マイクロフロー法ならでは」の手法論開発を目指して Invited

    布施新一郎

    マイクロ化学生産研究コンソーシアム講演会および成果報告会 

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    Event date: 2015.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:京都大学桂キャンパス 京都   Country:Japan  

  140. An efficient amide bond formation through the rapid and strong activation of carboxylic acids in a micro-flow reactor Invited International conference

    Shinichiro Fuse

    International Conference on Nascent Developments in Chemical Sciences 2015 (NDCS-2015): Opportunities for Academia-Industry Collaboration 

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    Event date: 2015.10

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Birla Institute of Technology and Science India   Country:India  

  141. マイクロフロー合成法を駆使する高 選択的反応を基軸とした天然物合成

    布施新一郎

    日本化学会第95春季年会 

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    Event date: 2015.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:日本大学船橋キャンパス 千葉   Country:Japan  

  142. Utilization of micro-flow technology for the site-selective modification of multi-functionalized molecules Invited International conference

    Shinichiro Fuse

    8th Singapore International Chemistry Conference 2014 

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    Event date: 2014.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:National Univeristy of Singapore Singapore   Country:Singapore  

  143. フローでおこなうペプチドの超高速合成 Invited

    布施新一郎

    新学術領域研究「反応集積化の合成化学 革新的手法の開拓と有機物質創成への展開」研究成果とりまとめシンポジウム 

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    Event date: 2014.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:京都大学 京都   Country:Japan  

  144. Highly Efficient Amide Bond Formation via Flash Activation of Carboxylic Acids in Microreactors Invited

    Shinichiro Fuse

    The Eighth International Symposium on Integrated Synthesis 

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    Event date: 2013.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Todaiji Temple Cultural Center Nara Japan   Country:Japan  

  145. 自動・マイクロフロー合成法を駆使する高効率天然物合成 Invited

    布施新一郎

    メトラー・トレド日本RXE Forum 2013 

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    Event date: 2013.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:日本科学未来館 東京   Country:Japan  

  146. マイクロフロー合成法を駆使する高効率天然物合成 Invited

    布施新一郎

    日本農芸化学会2013年度大会 

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    Event date: 2013.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東北大学川内北キャンパス 宮城   Country:Japan  

  147. フローマイクロリアクターを用いたビタミンD3類、ペプチドの効率合成 Invited

    布施新一郎

    近畿化学協会フロー・マイクロ合成研究会第57回研究会 

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    Event date: 2013.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:かんぽの宿 福井   Country:Japan  

  148. 光・熱反応の空間的集積化を基盤とするビタミンD3類の効率的マイクロフロー合成法の開発 Invited

    布施 新一郎

    近畿化学協会フロー・マイクロ合成研究会第53回研究会 

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    Event date: 2012.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:大阪科学技術センター 大阪   Country:Japan  

  149. Efficient Organic Synthesis Using a Continuous-flow System Invited International conference

    Shinichiro Fuse

    Senior Workshop: Advanced Version of WOCJC 

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    Event date: 2011.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Tokyo Institute of Technology Tokyo Japan   Country:Japan  

  150. 自動合成・フロー合成技術を活用した天然物合成 Invited

    布施 新一郎

    第35回星薬科大学大学院研究科助手会・大学院学生自治会合同公開セミナー 

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    Event date: 2011.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:星薬科大学 東京   Country:Japan  

  151. 減生、再構築法を基盤とする抗生物質Moenomycin Aの構造活性相関研究 Invited

    布施新一郎

    第42回天然物化学談話会 

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    Event date: 2007.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:秋保リゾートホテル クレセント 宮城   Country:Japan  

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Research Project for Joint Research, Competitive Funding, etc. 1

  1. 多様なモダリティを実現する有機合成の高度化と生命科学・創薬研究の支援

    Grant number:JP22am121044  2022.4 - 2027.3

    生命科学・創薬研究支援基盤事業  化合物の構造展開によるリード探索・最適化の支援と高度化

    布施新一郎

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    Authorship:Coinvestigator(s)  Grant type:Competitive

    Grant amount:\53882530 ( Direct Cost: \41448100 、 Indirect Cost:\12434430 )

KAKENHI (Grants-in-Aid for Scientific Research) 12

  1. P-キラル光学活性リン化合物を導く高効率高選択的連続反応の開発

    Grant number:22K05109  2022.4 - 2025.3

    科学研究費助成事業  基盤研究(C)

    村井 利昭, 布施 新一郎

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    Authorship:Coinvestigator(s) 

    本研究では、リン原子がキラル中心である四配位五価リン化合物群のうち、生理活性、薬理活性を示すものも多く含まれる、リン原子上に少なくとも炭素置換基が一つと、窒素、酸素あるいは硫黄置換基を有する化合物群を標的化合物として、われわれが独自に発見したビナフチル基のキラリティー転写反応、リン原子上置換反応を経由して、それらを高効率かつ高い鏡像異性体比で導く系を構築する。さらに鍵出発化合物への異なる二つの求核剤の付加を連続で行い標的化合物を得るとともに、ビナフトールを回収再利用できる系を、フロー合成法を駆使して提供する。

  2. 低エントロピー反応空間での短寿命複合体制御を起点とする有機分子触媒化学の変革

    Grant number:21H05081  2021.8 - 2024.3

    日本学術振興会  科学研究費助成事業  学術変革領域研究(B)

    布施 新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\32760000 ( Direct Cost: \25200000 、 Indirect Cost:\7560000 )

    本研究では、触媒反応開発において利用が忌避されてきた、短寿命の不安定複合体に関する化学的知見蓄積を基盤として、従来の合成手法では実現困難な反応プロセスの開発を目指す。すなわち、本研究では有機分子触媒反応、特に求核性アミン触媒と求電子剤から生成する、律速段階直前の不安定複合体に焦点を当て、複合体を高秩序かつ均一に生成させて反応を詳細に解析し、学術的な知見蓄積と反応設計原理の探求を進める。また、これまでの常識を覆すペプチド合成法の開発を第一歩とし、有機分子触媒化学の変革を目指す。

  3. Making a summary of highly organized catalytic reaction chemistry realized by low entropy reaction space

    Grant number:21H05079  2021.8 - 2024.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Transformative Research Areas (B)

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    Authorship:Coinvestigator(s) 

  4. 高求電子性リン反応剤を用いるリン酸トリエステル合成の機構解明と応用展開

    Grant number:21H01929  2021.4 - 2025.3

    日本学術振興会  科学研究費助成事業  基盤研究(B)

    布施 新一郎, 増井 悠

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    Authorship:Principal investigator 

    Grant amount:\17160000 ( Direct Cost: \13200000 、 Indirect Cost:\3960000 )

    本研究は医薬品として重要なリン酸トリエステルを、自在に高収率で速やかに合成できる手法の確立を最終目標に定める。これを実現するため、安価で高活性なリン含有原料に対し、多様な構造の異なるアルコールを連続的に導入するアプローチを開発する。通常、このようなアプローチでは競合する副反応の回避が困難である。これに対して、本研究では微小な流路内で反応させるマイクロフロー合成法を駆使した解決を目指す。すなわち、マイクロフロー合成法を利用することでフラスコを用いた反応では困難な反応時間・温度の精密制御が実現するため、これらの特徴を活かすことで、高効率的なリン酸トリエステルの合成を実現する。

  5. Creation of New Concept in Synthesis of Cyclic Peptide

    Grant number:20K21188  2020.7 - 2022.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Research (Exploratory)

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\6240000 ( Direct Cost: \4800000 、 Indirect Cost:\1440000 )

  6. 超高効率なマイクロフロー亜リン酸ジエステル形成法開発と中分子核酸合成への展開

    Grant number:18H04392  2018.4 - 2020.3

    日本学術振興会  科学研究費補助金  新学術領域研究(研究領域提案型)

    布施 新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\5200000 ( Direct Cost: \4000000 、 Indirect Cost:\1200000 )

    核酸医薬品は、抗体医薬品と低分子医薬品の双方の長所を併せもつため夢の次世代医薬品として脚光を浴びている。その一般的合成法(ホスホロアミダイト法)は高価な試薬や基質を要する。ホスホロアミダイト法の開発以来35年以上の間、世界中の研究者が新合成法開発に挑んできたが問題は未解決のままである。本申請では、マイクロフロー法を駆使してこの難題の解決に挑む。三塩化リンはリンと塩素から合成され、ほとんどのリン化合物の源となっている最も高活性・安価・単純な構造の化合物であるが、反応性の制御が困難なため核酸合成分野では実用性がないと見なされてきた。本申請では、この三塩化リンに焦点をあて、マイクロフロー法による反応性の制御を基盤とする亜リン酸ジエステル形成法の開発とこれを用いる中分子オリゴ核酸合成への展開を図る。
    H30年度は当初チミジンと三塩化リンと水の反応の検討から開始する予定であったが、反応成績の評価が予想以上に困難であったため、脂肪族の1級アルコールと2級アルコールをチミジンの代わりとして用いて三塩化リンに対する求核置換反応の選択性を評価した。その結果、マイクロフロー法の得意とする高速混合技術を用いることにより高選択的に目的物が得られることを確認した。良好な反応成績(選択性)を得るためには溶媒や温度の選択が極めて重要であること、確立した条件を旧来のバッチ条件で行うと、ほとんど選択性が観察されないことも明らかにした。
    H30年度は当初計画していたチミジンでの反応検討ではなくなったものの、モデル基質を用いることにより当初期待していたとおりの高い選択性を得ることに成功し、しかもこの選択性はマイクロフロー法を用いなくては得られないものであることも実証した。
    モデル基質を用いた検討では、期待した選択性で目的のリン酸ジエステルを得ることに成功したので、今後当初使用予定であったチミジンを用いる検討を行う。なおこの際に二段階目の反応(2級アルコールの求核置換反応)が焦点となる。P(OR)Cl2を合成して、これを用いる選択的な2級アルコール導入条件の確立を行い、その後、PCl3を用いてリン酸ジエステルを合成する検討へつなげる。

  7. Development of high atom economy peptide chain elongation in a micro-flow reactor using unprotected amino acids

    Grant number:17H03053  2017.4 - 2021.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    Shinichiro Fuse

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\17420000 ( Direct Cost: \13400000 、 Indirect Cost:\4020000 )

    Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. We developed peptide chain elongation using unprotected amino acids via mixed carbonic anhydride. Micro-flow technology enabled rapid mixing of an organic layer containing a protected amino acid or dipeptide and an aqueous layer containing an unprotected amino acid or dipeptide to accelerate the desired amidation, and this approach successfully suppressed undesired racemization/epimerization. Various peptides were obtained in good to high yields.

  8. 超高効率なマイクロフローアミド化法の開発と中分子フェグリマイシン合成への展開

    Grant number:16H01138  2016.4 - 2018.3

    日本学術振興会  科学研究費補助金  新学術領域研究(研究領域提案型)

    布施 新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\5590000 ( Direct Cost: \4300000 、 Indirect Cost:\1290000 )

    本申請研究では、α-アミノ酸-N-カルボキシ無水物の調製とそのマイクロフローアミド結合形成反応への利用、さらに開発するアミド結合形成反応を利用した天然由来抗菌・抗HIVペプチド、フェグリマイシンの全合成を目的とした。マイクロフロー法を用いてα-アミノ酸-N-カルボキシ無水物の新調製法を発見し、H28年度には調製したα-アミノ酸-N-カルボキシ無水物を用いてアミド結合形成を検討した。しかしながら、α-アミノ酸-N-カルボキシ無水物の反応性が予想以上に低かったため、目的物は得られたものの、目標収率におよばない結果となったため、本検討に関しては、H29年度も継続することとした。
    α-アミノ酸-N-カルボキシ無水物を用いるアミド結合形成法は原子効率が非常に高く、生じる夾雑物も除去しやすいことから理想的な方法であるが、様々な検討にもかかわらずやはり収率向上が極めて困難であった。このことから、α-アミノ酸-N-カルボキシ無水物を用いるアミド結合形成法の開発を断念し、混合炭酸無水物を利用する合成手法の開発に着手した。様々な検討を行った結果、収率良く目的物を得られる反応条件を見出した。混合炭酸無水物を用いる手法ではアミノ基の保護基は必要になるものの、研究代表者が過去に開発した対称酸無水物法と異なり、アミンとして用いるアミノ酸とカルボン酸として用いるアミノ酸をほぼ1対1の量比で反応させられることから、廃棄物を低減できる。このことから本研究で見出された成果は大きな意義をもつものである。
    29年度が最終年度であるため、記入しない。
    29年度が最終年度であるため、記入しない。

  9. Development of high atom economy synthesis of cyclic peptides based on sequential amidation-cyclization

    Grant number:15K17852  2015.4 - 2018.3

    Fuse Shinichiro

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

    Aim of this research was development of peptide chain elongation using alpha-amino acid-N-carboxy anhydride and photochemical cyclization of peptides for efficient cyclic peptide synthesis. We successfully developend and reported photochemical cyclization of peptides in an academic journal. On the other hand, peptide chain elongation using alpha-aminoacid-N-carboxy anhydride was rather difficult. In the couse of our research, however, we developed new synthetic approach for alpha-aminoacid-N-carboxy anhydrides. It alllowed us to synthesize alpha-aminoacid-N-carboxy anhydride that could not be synthesized by previously reported synthetic approaches.

  10. 反応系内発生ホスゲンを用いるペプチドの連続的マイクロフロー合成法開発

    Grant number:24106708  2012.4 - 2014.3

    日本学術振興会  科学研究費補助金  新学術領域研究(研究領域提案型)

    布施新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\6760000 ( Direct Cost: \5200000 、 Indirect Cost:\1560000 )

  11. 多段階連続マイクロフロー合成装置による活性型ビタミンD3類の高効率合成法の確立

    Grant number:23750101  2011.4 - 2014.3

    日本学術振興会  科学研究費助成事業  若手研究(B)

    布施新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4420000 ( Direct Cost: \3400000 、 Indirect Cost:\1020000 )

  12. 一酸化炭素ナノバブルを活用するフロー系超高効率連続的カルボニル化反応の開発

    Grant number:22106509  2010.4 - 2012.3

    文部科学省  科学研究費補助金  新学術領域研究(研究領域提案型)

    布施新一郎

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\7020000 ( Direct Cost: \5400000 、 Indirect Cost:\1620000 )

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