Updated on 2022/01/28

写真a

 
OTA, Eisuke
 
Affiliation
Faculty of Science and Engineering, School of Advanced Science and Engineering
Job title
Assistant Professor(without tenure)

Education

  • 2010.04
    -
    2016.03

    Keio University   Graduate School of Science and Technology  

  • 2006.04
    -
    2010.03

    Keio University   Faculty of Science and Engineering  

Degree

  • 慶應義塾大学   博士(理学)

Research Experience

  • 2020.04
    -
    Now

    Waseda University   Department of Applied Chemistry   Assistant Profesor

  • 2018.10
    -
    2020.03

    Waseda University   Waseda Research Institute for Science and Engineering   Assistant Professor

  • 2017.04
    -
    2018.09

    Princeton University   Department of Chemistry   JSPS Postdoctoral Fellowship for Research Abroad

  • 2016.04
    -
    2017.03

    RIKEN   Postdoctoral Researcher

  • 2014.04
    -
    2016.03

    Japan Society for the Promotion of Science (JSPS)   Research Fellowship for Young Scientist (DC2)

  • 2012.04
    -
    2014.03

    RIKEN   Junior Research Associate Program

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Research Areas

  • Synthetic organic chemistry

Research Interests

  • Natural Products Chemistry

  • Organic Photochemistry

  • Chemical Biology

  • Synthetic Organic Chemistry

Papers

  • Ganglioside GM3 Analogues Containing Monofluoromethylene-Linked Sialoside: Synthesis, Stereochemical Effects, Conformational Behavior, and Biological Activities

    Go Hirai, Marie Kato, Hiroyuki Koshino, Eri Nishizawa, Kana Oonuma, Eisuke Ota, Toru Watanabe, Daisuke Hashizume, Yuki Tamura, Mitsuaki Okada, Taeko Miyagi, Mikiko Sodeoka

    JACS Au   1 ( 2 ) 137 - 146  2021.02

    DOI

  • Synthesis of a pentaarylcarbazole: Installation of different aryl groups on a benzenoid moiety

    Tanaka, S., Asako, T., Ota, E., Yamaguchi, J.

    Chemistry Letters   49 ( 8 )  2020

    DOI

  • Synthesis of Decaarylanthracene with Nine Different Substituents

    Asako, T., Suzuki, S., Tanaka, S., Ota, E., Yamaguchi, J.

    Journal of Organic Chemistry    2020

    DOI

  • Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

    Takayuki Hoshi, Eisuke Ota, Yasuhide Inokuma, Junichiro Yamaguchi

    Organic Letters   21 ( 24 ) 10081 - 10084  2019.12  [Refereed]

     View Summary

    Copyright © 2019 American Chemical Society. A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

    DOI PubMed

  • A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions

    Eisuke Ota, Huaiju Wang, Nils Lennart Frye, Robert R. Knowles

    Journal of the American Chemical Society   141 ( 4 ) 1457 - 1462  2019.01  [Refereed]

     View Summary

    © 2019 American Chemical Society. We report a general protocol for the light-driven isomerization of cyclic aliphatic alcohols to linear carbonyl compounds. These reactions proceed via proton-coupled electron-transfer activation of alcohol O-H bonds followed by subsequent C-C β-scission of the resulting alkoxy radical intermediates. In many cases, these redox-neutral isomerizations proceed in opposition to a significant energetic gradient, yielding products that are less thermodynamically stable than the starting materials. A mechanism is presented to rationalize this out-of-equilibrium behavior that may serve as a model for the design of other contrathermodynamic transformations driven by excited-state redox events.

    DOI PubMed

  • Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling

    Eisuke Ota, Kazuteru Usui, Kana Oonuma, Hiroyuki Koshino, Shigeru Nishiyama, Go Hirai, Mikiko Sodeoka

    ACS Chemical Biology   13 ( 4 ) 876 - 880  2018.04  [Refereed]

     View Summary

    © 2018 American Chemical Society. Photoaffinity labeling (PAL) is an important tool in chemical biology research, but application of α-ketoamides for PAL has been hampered by their photoinstability. Here, we show that 2-thienyl-substituted α-ketoamide is a superior photoreactive group for PAL. Studies with a series of synthetic mannose-conjugated α-ketoamides revealed that 2-thienyl substitution of α-ketoamide decreased the electrophilicity of the keto group and reduced the rate of photodegradation. Mannose-conjugated thienyl α-ketoamide showed greater concanavalin A labeling efficiency than other alkyl or phenyl-substituted α-ketoamides. In comparison with representative conventional photoreactive groups, 2-thienyl ketoamide showed reduced labeling of nontarget proteins, probably owing to its lower hydrophobicity.

    DOI PubMed

  • Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation

    Qianqian Wang, Yuta Kuramoto, Yozo Okazaki, Eisuke Ota, Masaki Morita, Go Hirai, Kazuki Saito, Mikiko Sodeoka

    Tetrahedron Letters   58 ( 30 ) 2915 - 2918  2017  [Refereed]

     View Summary

    © 2017 Elsevier Ltd We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyldiacylglycerol (GlcADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected α-isomer of GlcADG as the major product.

    DOI

  • Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C-H Bond Activation

    Eisuke Ota, Yu Mikame, Go Hirai, Shigeru Nishiyama, Mikiko Sodeoka

    Synlett   27 ( 7 ) 1128 - 1132  2016.01  [Refereed]

     View Summary

    © Georg Thieme Verlag. We developed a photo-chemical coupling reaction of α-keto esters with several simple alcohols, alkanes, ethers, and amides. Use of tertiary alkyl ester, α-cumyl ester, is the key for avoiding the known photo-degradation process. Intermolecular C-H bond activation and subsequent C-C bond formation were promoted by irradiation with an LED lamp (365 nm) without any additives. Among the coupling partners, reactions with sterically less demanding amides proceeded efficiently to provide unique N-acyl-β-amino-α-hydroxy acid derivatives. In benzene or acetone as a solvent, the reaction with a solid amino acid derivative provided a precursor of tetrahydro-1,4-diazepine-2,5-dione derivatives.

    DOI

  • Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation

    Eisuke Ota, Yu Mikame, Go Hirai, Hiroyuki Koshino, Shigeru Nishiyama, Mikiko Sodeoka

    Tetrahedron Letters   56 ( 44 ) 5991 - 5994  2015.10  [Refereed]

     View Summary

    © 2015 Elsevier Ltd. A novel type of photocyclization of α-ketoamides was developed, affording unique cyclopropanols bearing amide functionality. N-tert-Butyl, N-trityl, or N-non-substituted α-ketoamides with a bulky substituent at the β-position of the amide functionality were efficiently converted to corresponding cyclopropanols through the activation of the γ-C-H bond followed by C-C bond formation between the α- and γ-positions of the amide. Hydrogen abstraction from the γ-position of the amide was considered to be the rate-determining step of cyclopropanol formation, based on the kinetic isotope effect. Cyclopropanols could be converted to two different types of functionalized α-ketoamides depending on the method of ring-opening.

    DOI

  • C-Sialosides: Synthesis and biological activities

    Go Hirai, Eisuke Ota, Motonari Sakai, Shigeru Nishiyama, Mikiko Sodeoka

    Trends in Glycoscience and Glycotechnology   27 ( 154 ) 47 - 60  2015  [Refereed]

     View Summary

    © 2015 FCCA (Forum: Carbohydrates Coming of Age). This mini-review focuses on the synthesis and biological activities of sialic acid (SA) derivatives with a C-glycosidic linkage in place of the standard O-glycosidic bond at the C-2 position. We summarize reported synthetic methodologies for monoand di-saccharides in separate sections. Then, we introduce our strategy for the construction of C-sialoside linkages utilizing Ireland-Claisen rearrangement reaction and its application to the synthesis of a ganglioside GM4 analogue. Although C-sialosides are expected to be useful as sialidase-resistant analogues of sialoglycoconjugates (sialoGCs), their biological activities have not yet been investigated in detail. Herein we briefly discuss the potential applications of C-sialosides.

    DOI

  • Synthesis and biological evaluation of molecular probes based on the 9-methylstreptimidone derivative DTCM-glutarimide

    Eisuke Ota, Masatoshi Takeiri, Miyuki Tachibana, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

    Bioorganic and Medicinal Chemistry Letters   22 ( 1 ) 164 - 167  2012.01  [Refereed]

     View Summary

    Molecular probes based on 3-[(dodecylthiocarbonyl)methyl]glutarimide (DTCM-glutarimide) were synthesized and assessed for inhibitory activity against LPS-induced NO production. Among the probes examined, several derivatives exhibited potential for use in determining the target proteins of DTCM-glutarimide. © 2011 Elsevier Ltd. All rights reserved.

    DOI PubMed

  • Structure-activity relationship of 9-methylstreptimidone, a compound that induces apoptosis selectively in adult T-cell leukemia cells

    Masatoshi Takeiri, Eisuke Ota, Shigeru Nishiyama, Hiromasa Kiyota, Kazuo Umezawa

    Oncology Research   20 ( 1 ) 7 - 14  2012  [Refereed]

     View Summary

    We previously reported that 9-methylstreptimidone, a piperidine compound isolated from a culture filtrate of Streptomyces, induces apoptosis selectively in adult T-cell leukemia cells. It was screened for a compound that inhibits LPS-induced NF-κB and NO production in mouse macrophages. However, 9-methystreptimidone is poorly obtained from the producing microorganism and difficult to synthesize. Therefore, in the present research, we studied the structure-activity relationship to look for new selective inhibitors. We found that the structure of the unsaturated hydrophobic portion of 9-methylstreptimidone was essential for the inhibition of LPS-induced NO production. Among the 9-methylstreptimidone-related compounds tested, (±)-4,α-diepi-streptovitacin A inhibited NO production in macrophage-like cells as potently as 9-methylstreptimidone and without cellular toxicity. Moreover, this compound selectively induced apoptosis in adult T-cell leukemia MT-1 cells. Copyright © 2012 Cognizant Comm. Corp. All rights reserved.

    DOI PubMed

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Misc

  • 「かご」に包まれた内因性カンナビノイドを光で放出する

    太田 英介

    ファルマシア   56 ( 6 ) 563 - 563  2020

     View Summary

    ケージド化合物は光照射によって除去可能な保護基(photoremovable protecting group: PRPG)を持つ化合物の総称である.代表的なPRPGの中でも,クマリン誘導体は高いモル吸光係数と分解速度を示し,比較的長波長の光で除去可能である.またクマリン自身が蛍光分子であるため,反応過程を追跡可能な点も魅力的である.保護可能な官能基も幅広く,アルコール,アミン,チオール,ケトン,カルボン酸,リン酸などのケージド化合物が知られる.本稿では,クマリン誘導体が1,3-ジオールの保護に適用できることを示し,光照射によって生細胞内の2-アラドノイルグリセロール(2-arachidonoylglycerol: 2-AG)量の調節に成功したSchultzらの成果を紹介する.<br>なお,本稿は下記の文献に基づいて,その研究成果を紹介するものである.<br>1) Laguerre A. et al., J. Am. Chem. Soc., 141, 16544-16547(2019).<br>2) Nadler A. et al., Nat. Commun., 6, 10056(2015).<br>3) Höglinger D. et al., eLife, 4, e10616(2015).<br>4) Lin W., Lawrence D. S., J. Org. Chem., 67, 2723-2726(2002).

    DOI CiNii

Research Projects

  • 環歪みの小さいエーテルの炭素-酸素σ結合開裂反応の開発

    日本学術振興会  科学研究費助成事業 若手研究

    Project Year :

    2020.04
    -
    2023.03
     

    太田 英介

  • 早稲田大学 特定課題(研究基盤形成)

    Project Year :

    2021
    -
    2022
     

  • 里見奨学会 研究提案表彰

    Project Year :

    2020
    -
    2021
     

  • 早稲田大学 特定課題(研究基盤形成)

    Project Year :

    2020
    -
    2021
     

  • 住友財団基礎科学研究助成

    Project Year :

    2019
    -
    2020
     

  • JXTG 若手奨励研究

    JXTG  若手奨励研究

    Project Year :

    2019
    -
    2020
     

  • 福岡直彦記念財団助成金

    福岡直彦記念財団  福岡直彦記念財団助成金

    Project Year :

    2019
    -
    2020
     

  • 理工学術院総合研究所 奨励研究

    理工学術院総合研究所  奨励研究

    Project Year :

    2019
    -
    2020
     

  • Waseda Research Institute for Science and Engineering Research Grant

    Waseda University 

    Project Year :

    2018.10
    -
    2019.03
     

    Eisuke Ota

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Specific Research

  • 高エネルギー中間体を利用した単結合開裂反応の開発

    2020   山口潤一郎

     View Summary

    今回、我々はジルコノセンがエポキシドのC–O結合均等開裂に利用できることを初めて明らかにした。可視光レドックス触媒およびジルコノセン触媒存在下、非対称エポキシドに対し青色LEDを照射することで、対応するアルコールが得られる。本反応は従来のチタノセンを用いた開環反応とは異なり、より置換数の少ない炭素上でC–O結合が開裂する。量子化学計算から、反応の位置選択性決定段階がチタノセンとジルコノセンで異なることも示唆された。本反応には多様な官能基をもつ基質が利用でき、天然物を含む複雑な分子にも適用可能である。

 

Syllabus

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