Toshima, Kazunobu

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry （Yagami）

Position

Professor

Related Websites

External Links
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Career 【 Display / hide 】

  • 1988.04
    -
    1989.03

    ペンシルバニア大学化学科 ,博士研究員

  • 1989.04
    -
    1994.03

    慶應義塾大学（理工学部） ,助手

  • 1994.04
    -
    1996.03

    慶應義塾大学（理工学部） ,専任講師

  • 1996.04
    -
    2003.03

    慶應義塾大学理工学部（応用化学科）,助教授

  • 1997.04
    -
    1999.03

    慶應義塾大学理工学応用化学科教室幹事

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Academic Background 【 Display / hide 】

  • 1983.03

    Keio University, Faculty of Engineering, 応用化学科

    University, Graduated

  • 1985.03

    Keio University, Graduate School, Division of Engineering, 応用化学専攻

    Graduate School, Completed, Master's course

  • 1988.03

    Keio University, Graduate School, Division of Science and Engineeri, 応用科学専攻

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • 工学　, Keio University, 1988.03

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Bio chemistry

  • Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules

  • Nanotechnology/Materials / Chemical biology

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Books 【 Display / hide 】

  • Comprehensive Glycoscience 2nd edition

    DAISUKE TAKAHASHI, Kazunobu Toshima, Elsevier, 2021.06

    Scope: 1,2-cis O-Glycosylation methods, Vol. 2, pp. 365-412.

  • 標的糖鎖光分解用生体機能分子、糖鎖の新機能開発・応用ハンドブック

    TAKAHASHI DAISUKE,TOSHIMA KAZUNOBU, エヌ・ティー・エス, 2015.08

    Scope: 377-379

  • 環境調和型グリコシル化反応、 糖鎖の新機能開発・応用ハンドブック

    SASAKI KANAME,TAKAHASHI DAISUKE,TOSHIMA KAZUNOBU, エヌ・ティー・エス, 2015.08

    Scope: 339-342

  • Stereoselective formation of 2-deoxyglycosidic bonds in biologically active natural products

    TAKAHASHI DAISUKE, TOSHIMA KAZUNOBU, Wiley, 2013

    Scope: 1137-1171

  • Green Solvents Ⅱ

    SASAKI KANAME, TAKAHASHI DAISUKE, TOSHIMA KAZUNOBU, Springer, 2012

    Scope: 67-78

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Papers 【 Display / hide 】

  • 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

  • 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)   2023

    Last author, 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.

  • 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

    Last author, 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

    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.

  • Self-Assembling Properties and Recovery Effects on Damaged Skin Cells of Chemically Synthesized Mannosylerythritol Lipids.

    Takanori Kondo, Chihiro Yasui, Taisuke Banno, Kouichi Asakura, Tokuma Fukuoka, Kazunori Ushimaru, Maito Koga, Hiroyuki Minamikawa, Azusa Saika, Tomotake Morita, Daisuke Takahashi, Kazunobu Toshima

    Chembiochem : a European journal of chemical biology （ChemBioChem)  23 （ 2 ） e202100631 2022.01

    Last author, Corresponding author, Accepted,  ISSN  14394227

    　View Summary

    Mannosylerythritol lipids (MELs), which are one of the representative sugar-based biosurfactants (BSs) produced by microorganisms, have attracted much attention in various fields in the sustainable development goals (SDGs) era. However, they are inseparable mixtures with respect to the chain length of the fatty acids. In this study, self-assembling properties and structure-activity relationship (SAR) studies of recovery effects on damaged skin cells using chemically synthesized MELs were investigated. It was revealed, for the first time, that synthetic and homogeneous MELs exhibited significant self-assembling properties to form droplets or giant vesicles. In addition, a small difference in the length of the fatty acid chains of the MELs significantly affected their recovery effects on the damaged skin cells. MELs with medium or longer length alkyl chains exhibited much higher recovery effects than that of C18-ceramide NP.

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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), Last 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, Last 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, Lead author, Corresponding 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, Last author, Corresponding author

  • マンノシルエリスリトールリピッド（MEL）の効率的全合成と抗菌活性を指標とした構造－機能相関の解明

    *高橋大介, *戸嶋一敦

    オレオサイエンス 20 ( 5 ) 209 - 214 2020.05

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

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Presentations 【 Display / hide 】

  • 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)

  • 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)

  • 非対称化型グリコシル化反応を用いたカナマイシンAの全合成研究

    今井万丈, 戸嶋一敦, 高橋大介

    GlycoTOKYO2022, 

    2022.12
    , 

    Poster presentation

  • 固体酸を用いた環境調和型C-グリコシル化反応の開発

    松本稜太, 高橋大介, 戸嶋一敦

    GlycoTOKYO2022, 

    2022.12
    , 

    Poster presentation

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

  • 天然物を基本骨格とする刺激応答型光感受性分子の創製と次世代型光線力学療法への応用

    2022.04
    -
    2026.03

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

  • 機能複合化による生体機能光制御中分子の創製

    2016.04
    -
    2018.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research on Innovative Areas, Principal investigator

  • Creation of agents that selectively photo-degrade certain proteins and oligosaccharides and its application to control of cell functions

    2014.04
    -
    2017.03

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

    　View Summary

    Several agents, that target-selectively photo-degrade certain disease-related proteins and oligosaccharides, were designed and synthesized. Furthermore, it was found the agents thus developed work not only in test tube but also in disease-related cells. From these studies, a new approach for the design of light-activated and molecular-targeted medicines has been established.

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Intellectual Property Rights, etc. 【 Display / hide 】

  • 抗腫瘍活性を有する硫酸化オリゴフコシド類

    Date applied： 特願2013-150907  2013.07 

    Patent, Joint

  • ノイラミニダーゼに対する酵素阻害剤

    Date applied： 特願2010-022168  2009.02 

    Patent, Joint

  • 光増感剤、タンパク質切断剤、タンパク質切断方法、糖分子切断剤、糖分子切断方法、及び光線力学治療剤

    Date applied： 特願2007-507210  2006.03 

    Date issued： 特許第5046029号  2012.07

    Patent, Single

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Awards 【 Display / hide 】

  • SSOCJ Daiichi-Sankyo Award for Medicinal Organic Chemistry 2015

    2016.02

  • 日本化学会学術賞

    2015.03

  • 山下太郎学術研究奨励賞

    1996.05

  • 日本化学会進歩賞

    1995.03

  • 油脂技術優秀論文賞

    戸嶋 一敦, 1995.02, 油脂工業会館

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Courses Taught 【 Display / hide 】

  • SEMINAR IN APPLIED CHEMISTRY

    2023

  • MOLECULAR LIFE CHEMISTRY 1

    2023

  • LABORATORIES IN APPLIED CHEMISTRY D

    2023

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2023

  • GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

    2023

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Memberships in Academic Societies 【 Display / hide 】

  • 日本ケミカルバイオロジー学会, 

    2007.04
    -
    Present

  • 高分子学会, 

    2004.07
    -
    Present

  • 日本糖質学会, 

    1991.03
    -
    Present

  • アメリカ化学会, 

    1988.06
    -
    Present

  • 有機合成化学協会, 

    1986.01
    -
    Present

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Committee Experiences 【 Display / hide 】

  • 2014.11
    -
    Present

    幹事, GlycoTokyo

  • 2014.04
    -
    Present

    評議員, 日本糖質学会

  • 2007.04
    -
    Present

    世話人, 日本ケミカルバイオロジー学会

  • 2006.04
    -
    2008.03

    関東支部常任幹事, 有機合成化学協会

  • 2006.04
    -
    2008.03

    事業委員会委員, 有機合成化学協会

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