Takahashi, Daisuke

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry Yagami Campus 23-603 （Yagami）

Position

Associate Professor

Related Websites

Contact Address

3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa

External Links
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Career 【 Display / hide 】

  • 2005.04
    -
    2006.03

    Japan Society for the Promotion of Science (JSPS) Research Fellow (DC2)

  • 2006.04
    -
    2007.03

    Japan Society for the Promotion of Science (JSPS) Research Fellow (PD)

  • 2007.04
    -
    2008.03

    Carlsberg Laboratory, Postdoctoral Fellow

  • 2008.04
    -
    2011.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate (Non-tenured)

  • 2011.04
    -
    2012.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate

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Academic Background 【 Display / hide 】

  • 1997.04
    -
    2001.03

    Tokyo Institute of Technology, Faculty of Engineering, Applied chemistry

    University, Graduated

  • 2001.04
    -
    2006.03

    Tokyo Institute of Technology, Graduate School of Science and Technology, Department of Applied Chemistry

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • Ph.D., Tokyo Institute of Technology, Coursework, 2006.03

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Carbohydrate Chemistry)

  • Life Science / Bioorganic chemistry (Carbohydrate Chemistry)

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Synthetic Organic Chemistry)

  • Life Science / Bioorganic chemistry (Synthetic Organic Chemistry)

  • Nanotechnology/Materials / Chemical biology

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Research Keywords 【 Display / hide 】

  • Carbohydrate Chemistry

  • Synthetic Organic Chemistry

  • Glycosylation Reaction

  • Chemical Biology

  • Glycosylated Natural Products

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Books 【 Display / hide 】

  • 1,2-cis O-Glycosylation Methods

    Takahashi D., Toshima K., Comprehensive Glycoscience: Second Edition, 2021.06

  • 糖鎖の新機能開発・応用ハンドブック

    高橋大介、戸嶋一敦, エヌ・ティー・エス, 2015.08

    Scope: 標的糖鎖光分解用生体機能分子, pp. 377-379.

  • 糖鎖の新機能開発・応用ハンドブック

    佐々木要、高橋大介、戸嶋一敦, エヌ・ティー・エス, 2015.08

    Scope: 環境調和型グリコシル化反応, pp. 339-342.

  • 機能性配糖体の合成と応用－糖転移酵素を中心に－

    関根麻衣子、高橋大介、戸嶋一敦, シーエムシー出版, 2013

    Scope: イオン液体を用いたバイオマス糖質からの配糖体合成, 第12章, pp. 115-123.

  • Stereoselective synthesis of drugs & natural products

    Daisuke Takahashi, Kazunobu Toshima, Wiley-Blackwell, 2012.03

    Scope: Stereoselective formation of 2-deoxy-glycosidic bonds in biologically active natural products. Chapter 38, pp. 1137-1171

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Papers 【 Display / hide 】

  • Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery

    Kazuki Inaba, Yuna Naito, Mina Tachibana, *Kazunobu Toshima, *DAISUKE TAKAHASHI

    ANGEWANDTE CHEMIE - INTERNATIONAL EDITION （Wiley)   2023.07

    Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted,  ISSN  14337851

    　View Summary

    Regio- and stereoselective formation of the 1,2-cis-furanosidic linkage has been in great demand for efficient synthesis of biologically active natural glycosides. In this study, we developed a regioselective and β-stereospecific d-/l-arabinofuranosylation promoted by a boronic acid catalyst under mild conditions. The glycosylations proceeded smoothly for a variety of diols, triols, and unprotected sugar acceptors to give the corresponding β-arabinofuranosides (β-Arbf) in high yields with complete β-stereoselectivity and high regioselectivity. The regioselectivity was completely reversed depending on the optical isomerism of the donor used and was predictable a priori using predictive models. Mechanistic studies based on DFT calculations revealed that the present glycosylation occurs through a highly dissociative concerted SNi mechanism. The usefulness of the glycosylation method was demonstrated by the chemical synthesis of trisaccharide structures of arabinogalactan fragments.

  • Photoinduced Glycosylation Using a Diarylthiophene as an Organo Lewis Photoacid Catalyst

    Naoki Otani, Kohei Higashiyama, Hayato Sakai, Taku Hasobe, *DAISUKE TAKAHASHI, *Kazunobu Toshima

    European Journal of Organic Chemistry （Wiley)  26 2023.04

    Research paper (scientific journal), Corresponding author, Accepted,  ISSN  1434193X

    　View Summary

    Here reports an photoinduced glycosylation of trichloroacetimidate donors and several alcohols using 3,11-dimethoxydinaphthothiophene as an organo Lewis photoacid catalyst upon long-wavelength UV-LED light (385 nm) irradiation. The reaction proceeded under mild reaction conditions smoothly to give the corresponding glycosides in good to high yields. In addition, the present glycosylation method was applicable to a wide range of trichloroacetimidate donors and acceptors. Furthermore, the dinaphthothiophene catalyst could be recovered and reused without any loss of efficiency. Moreover, this glycosylation method was applied successfully to the total synthesis of a biologically active natural product, cholesteryl 6-O-myristoyl-α-glucoside.

  • Destabilization of vitelline membrane outer layer protein 1 homolog (VMO1) by <i>C</i> ‐mannosylation

    Satoshi Yoshimoto, Takehiro Suzuki, Naoki Otani, DAISUKE TAKAHASHI, Kazunobu Toshima, Naoshi Dohmae, Siro Simizu

    FEBS Open Bio （Wiley)  13 （ 3 ） 490 - 499 2023.01

    Accepted,  ISSN  2211-5463

  • Synthesis of Mannosylerythritol Lipid Analogues and their Self-Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity.

    Takanori Kondo, Chihiro Yasui, Ikkei Miyajima, Taisuke Banno, Kouichi Asakura, Tokuma Fukuoka, Kazunori Ushimaru, Maito Koga, Azusa Saika, Tomotake Morita, Yoshiaki Takahashi, Chigusa Hayashi, Masayuki Igarashi, *DAISUKE TAKAHASHI, *Kazunobu Toshima

    CHEMISTRY-A EUROPEAN JOURNAL （Chemistry - A European Journal)  28 （ 55 ）  2022.10

    Corresponding author, Accepted,  ISSN  09476539

    　View Summary

    Synthesis of three types of purpose-designed mannosylerythritol lipid (MEL)-D analogues with decanoyl groups (C10), β-GlcEL-D, α-GlcEL-D, and α-MEL-D, was accomplished utilizing our boron-mediated aglycon delivery (BMAD) methods. Their self-assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. It was revealed, for the first time, that α-GlcEL-D and α-MEL-D only generated giant vesicles, indicating that slight differences in the steric configuration of an erythritol moiety and fatty acyl chains affect the ability to form vesicles. Analogue α-MEL-D exhibited significant recovery effects on damaged skin cells. Furthermore, α-MEL-D exhibited antibacterial activity as high as that for MEL-D, indicating that α-MEL-D is a promising artificial sugar-based material candidate for enhancing the barrier function of the stratum corneum, superior to a known cosmetic ingredient, and possesses antibacterial activity.

  • Efficient Strategy for the Preparation of Chemical Probes of Biologically Active Glycosides Using a Boron-Mediated Aglycon Delivery (BMAD) Method

    Kosuke Kimura, Takeshi Yasunaga, Takumi Makikawa, *DAISUKE TAKAHASHI, *Kazunobu Toshima

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN （The Chemical Society of Japan)  95 （ 7 ） 1075 - 1082 2022.07

    Corresponding author, Accepted,  ISSN  00092673

    　View Summary

    Development of an efficient method for the analysis and identification of the target proteins with which biologically active glycosides directly interact is highly desirable in many research fields. In this article, we report an efficient strategy for the preparation of chemical probes of biologically active glycosides using a reaction sequence of i) a boron-mediated aglycon delivery (BMAD) with an N3-functionalized 1,2-anhydroglu-cose donor, ii) deprotection, and iii) strain-promoted azidealkyne cycloaddition. Using the synthesized chemical probes, we successfully demonstrated that the target proteins of a cardiac glycoside, lanatoside C (1), can be visualized and identified in human colon cancer HCT116 cells.

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Papers, etc., Registered in KOARA 【 Display / hide 】

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Reviews, Commentaries, etc. 【 Display / hide 】

  • Boron-mediated aglycon delivery (BMAD) for the stereoselective synthesis of 1,2-cis glycosides

    *DAISUKE TAKAHASHI, Kazunobu Toshima

    Advances in Carbohydrate Chemistry and Biochemistry 82   79 - 105 2022.11

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Lead author, Corresponding author

  • Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

    *DAISUKE TAKAHASHI, Kazuki Inaba, *Kazunobu Toshima

    Carbohydrate Research (Carbohydrate Research)  518   108579 2022.08

    Joint Work, Lead author, Corresponding author,  ISSN  00086215

    　View Summary

    Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

  • Photo-induced Glycosylation Using Organophotoacids

    *Kazunobu Toshima;DAISUKE TAKAHASHI

    Bioindustry (シーエムシー出版)  38 ( 8 ) 3 - 11 2021.08

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Last author

  • Boron-Mediated Aglycon Delivery and Application to the Synthesis of Pathogenic Bacterial Oligosaccharides

    *DAISUKE TAKAHASHI;*Kazunobu Toshima

    Bioindustry (シーエムシー出版)  38 ( 8 ) 32 - 41 2021.08

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Lead author, Corresponding author

  • 【ディビジョン・トピックス】化学合成を駆使したワクチン開発への挑戦

    *DAISUKE TAKAHASHI

    化学と工業 74   513 - 513 2021.06

    Single Work, Lead author, Last author, Corresponding author

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Presentations 【 Display / hide 】

  • 新規有機光ルイス酸触媒を用いた光グリコシル化反応

    高橋大介

    CREST「革新的反応」研究成果報告会, 

    2023.03
    , 

    Oral presentation (invited, special)

  • Development of Novel Photosensitizers based on Naphthol Moiety of Enediyne Antibiotic N1999A2

    髙橋南美, 松永ことの, 加賀谷つぐみ, 高橋大介, 戸嶋一敦

    The 103th CSJ Annual Meeting (2023), 

    2023.03
    , 

    Oral presentation (general)

  • Regio- and Stereoselective β-Arabinofuranosylation Using a Boron-Mediated Aglycon Delivery Method

    Kazuki Inaba, Yuna Naito, Mina Tachibana, Kazunobu Toshima, Daisuke Takahashi

    The 103th CSJ Annual Meeting (2023), 

    2023.03
    , 

    Oral presentation (general)

  • Environmentally Benign C- and N-Glycosylations Utilizing Solid Acids

    松本 稜太, 高橋 大介, 戸嶋 一敦

    The 103th CSJ Annual Meeting (2023), 

    2023.03
    , 

    Oral presentation (general)

  • 有機化学を基盤とした人獣共通感染症に対する糖鎖医薬開発への挑戦

    高橋大介

    東京大学医科学研究所－千葉大学真菌医学研究センター合同成果報告会, 

    2023.03
    , 

    Oral presentation (invited, special)

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Research Projects of Competitive Funds, etc. 【 Display / hide 】

  • ホウ素媒介アグリコン転移を用いた1,2-cis フラノシドの精密化学合成と応用

    2023.04
    -
    Present

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

  • 広域スペクトルを有する抗ウイルス薬開発を目指した創薬標的探索と次世代創薬モダリティの基盤構築

    2022.10
    -
    Present

    AMED, AMED-CREST, Coinvestigator(s)

  • 「ルイス酸-外部刺激」系によるイオン性中間体の活性化

    2020.11
    -
    Present

    JST, CREST, Coinvestigator(s)

  • 有機化学を基盤とした人獣共通感染症に対する複合糖質ワクチン開発への挑戦

    2020.07
    -
    2022.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Challenging Research (Exploratory), Principal investigator

  • 非対称化型1,2-cis-立体選択的グリコシル化法の開発と有用糖質合成への応用

    2019.04
    -
    2023.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

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Awards 【 Display / hide 】

  • Oleomaterial award

    Daisuke Takahashi, 2022, Japan Oil Chemists' Society Oleomaterial Division, Efficient Total Synthesis of Mannosylerythritol Lipids and Their Structure-Function Studies

    Type of Award： Award from Japanese society, conference, symposium, etc.

  • The Carbohydrate Research Award for Creativity in Carbohydrate Chemistry

    2021, The Editorial Board and Publisher of Carbohydrate Research

    Type of Award： Award from publisher, newspaper, foundation, etc.

  • Incentive Award in Synthetic Organic Chemistry, Japan (2016)

    2017.02, The Society of Synthetic Organic Chemistry, Japan, Precise Synthesis and Chemical Biological Studies of Certain Carbohydrates, and Creation of Artificial Bio-functional Molecules

    Type of Award： Award from Japanese society, conference, symposium, etc.

  • 2016 Incentive Award in the Japanese Society of Carbohydrate Research

    2016.09, The Japanese Society of Carbohydrate Research, Target-Selective Synthesis and Photodegradation of Oligosaccharides Utilizing Chemical Properties of Organoboronic Acids

    Type of Award： Award from Japanese society, conference, symposium, etc.

  • 第30回若い世代の特別講演会　講演証

    TAKAHASHI Daisuke, 2016.03, 日本化学会, 芳香族ボロン酸の化学的特性を活用した標的糖鎖の選択的合成と光分解

    Type of Award： Award from Japanese society, conference, symposium, etc.

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Courses Taught 【 Display / hide 】

  • SEMINAR IN APPLIED CHEMISTRY

    2023

  • MOLECULAR LIFE CHEMISTRY 2

    2023

  • LABORATORY IN SCIENCE

    2023

  • LABORATORIES IN APPLIED CHEMISTRY D

    2023

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2023

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Courses Previously Taught 【 Display / hide 】

  • Molecular Life Chemistry 1

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Lecture, Within own ｆaculty, 1h

  • Molecular Life Chemistry 2

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Lecture, Within own ｆaculty, 1h

    糖鎖、化学合成、生合成、酵素合成、糖鎖生物学、癌、インフルエンザ

  • LABORATORIES IN APPLIED CHEMISTRY D

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Laboratory work/practical work/exercise, Within own ｆaculty

  • 生体物質化学基礎

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Lecture, Within own ｆaculty, 1h, 161people

  • GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

    Keio University

    2018.04
    -
    2019.03

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Memberships in Academic Societies 【 Display / hide 】

  • Japan Oil Chemists' Society, member, 

    2018.06
    -
    Present

  • American Chemical Society, member, 

    2017.11
    -
    Present

  • FCCA (Forum: Carbohydrates Coming of Age), member, 

    2012.09
    -
    Present

  • 日本ケミカルバイオロジー学会、会員, 

    2008
    -
    Present

  • 有機合成化学協会、会員, 

    2005
    -
    Present

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Committee Experiences 【 Display / hide 】

  • 2023.03
    -
    Present

    日本化学会　代表正会員, 日本化学会

  • 2023.01
    -
    Present

    Associate Editor, Trends in Glycoscience and Glycotechnology

  • 2023.01
    -
    Present

    TIGGトピック担当幹事, FCCA (Forum: Carbohydrates Coming of Age)

  • 2023.01
    -
    Present

    幹事会員, FCCA (Forum: Carbohydrates Coming of Age)

  • 2022.10
    -
    Present

    日本化学会2023年度代議員, 日本化学会

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