Toshima, Kazunobu

写真a

Affiliation

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

Position

Professor

Related Websites

External Links

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

display all >>

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

Academic Degrees 【 Display / hide

  • 工学 , Keio University, 1988.03

 

Research Areas 【 Display / hide

  • Biomolecular chemistry

  • Chemical biology

  • Synthetic chemistry

  • Bio-related chemistry

 

Books 【 Display / hide

  • 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

  • 進化を続ける有機触媒―有機合成を革新する第三の触媒

    TOSHIMA KAZUNOBU, 化学同人, 2009.07

display all >>

Papers 【 Display / hide

  • Synthesis of a Pentasaccharide Repeating Unit of Lipopolysaccharide Derived from Virulent E. coli O1 and Identification of a Glycotope Candidate of Avian Pathogenic E. coli O1

    Nobuya Nishi, Katsunori Seki, *Daisuke Takahashi, *Kazunobu Toshima

    Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  60 ( 4 ) 1789 - 1796 2021.01

    Research paper (scientific journal), Accepted,  ISSN  14337851

     View Summary

    © 2020 Wiley-VCH GmbH Avian pathogenic Escherichia coli (APEC) is a common bacterial pathogen infecting chickens, resulting in economic losses to the poultry industry worldwide. In particular, APEC O1, one of the most common serotypes of APEC, is considered problematic due to its zoonotic potential. Therefore, many attempts have been made to develop an effective vaccine against APEC O1. In fact, the lipopolysaccharide (LPS) O-antigen of APEC O1 has been shown to be a potent antigen for inducing specific protective immune responses. However, the detailed structure of the O-antigen of APEC O1 is not clear. The present study demonstrates the first synthesis of a pentasaccharide repeating unit of LPS derived from virulent E. coli O1 and its conjugate with BSA. ELISA tests using the semi-synthetic glycoconjugate and the APEC O1 immune chicken serum revealed that the pentasaccharide is a glycotope candidate of APEC O1, with great potential as an antigen for vaccine development.

    This paper was press-released from Keio University. (https://www.keio.ac.jp/ja/press-releases/2020/11/16/28-76321/)
    This paper was selected as a Hot Paper.
    This paper was selected as an inside back cover.

  • Diboron-Catalyzed Regio- and 1,2-cis-α-Stereoselective Glycosylation of trans-1,2-Diols.

    Shunpei Tomita, Masamichi Tanaka, Michitaka Inoue, Kazuki Inaba, *Daisuke Takahashi, *Kazunobu Toshima

    THE JOURNAL OF ORGANIC CHEMISTRY (American Chemical Society)  85 ( 24 ) 16254 - 16262 2020.12

    Research paper (scientific journal), Joint Work, Accepted

     View Summary

    Regio- and 1,2-cis-α-stereoselective glycosylations were investigated using 1,2-anhydroglucose donors and trans-1,2-diol sugar acceptors in the presence of a diboron catalyst. The reactions proceeded smoothly to provide the corresponding 1,2-cis-α-glycosides with consistently very high stereoselectivity and were regioselectivity controlled by the protecting groups of the acceptor. The present glycosylation method was applied successfully to the efficient synthesis of α-1,3-glucan pentasaccharide.

  • 2-Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein-Photodegrading Agent and Its Application as a H<inf>2</inf>O<inf>2</inf>-Activatable Photosensitizer

    Takashi Kitamura, Saori Shiroshita, *Daisuke Takahashi *Kazunobu Toshima

    Chemistry - A European Journal (Wiley-VCH )  26 ( 63 ) 14351 - 14358 2020.11

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  09476539

     View Summary

    © 2020 Wiley-VCH GmbH A 2-naphthol derivative 2 corresponding to the aromatic ring moiety of neocarzinostatin chromophore was found to degrade proteins under photo-irradiation with long-wavelength UV light without any additives under neutral conditions. Structure–activity relationship studies of the derivative revealed that methylation of the hydroxyl group at the C2 position of 2 significantly suppressed its photodegradation ability. Furthermore, a purpose-designed synthetic tumor-related biomarker, a H2O2-activatable photosensitizer 8 possessing a H2O2-responsive arylboronic ester moiety conjugated to the hydroxyl group at the C2 position of 2, showed significantly lower photodegradation ability compared to 2. However, release of the 2 from 8 by reaction with H2O2 regenerated the photodegradation ability. Compound 8 exhibited selective photo-cytotoxicity against high H2O2-expressing cancer cells upon irradiation with long-wavelength UV light.

  • Total Synthesis of Terpioside B

    Kazuki Inaba, Masato Endo, Naoto Iibuchi, Daisuke Takahashi, *Kazunobu Toshima

    Chemistry - A European Journal (Wiley-VCH )  26 ( 45 ) 10222 - 10225 2020.08

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  09476539

     View Summary

    © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d-galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l-fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations.

  • Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor

    Tanaka M., Sato K., Yoshida R., Nishi N., Oyamada R., Inaba K., *Takahashi D., *Toshima K.

    Nature Communications (Springer Nature)  11 ( 1 ) 2431 2020.05

    Research paper (scientific journal), Joint Work, Accepted

     View Summary

    © 2020, The Author(s). Chemical desymmetrization reactions of meso-diols are highly effective for the precise and efficient synthesis of chiral molecules. However, even though enzyme-catalyzed desymmetric glycosylations are frequently found in nature, there is no method for highly diastereoselective desymmetric chemical glycosylation of meso-diols. Herein, we report a highly diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols found in myo-inositol 1,3,5-orthoesters using a boronic acid catalyst based on predictions of regioselectivity by density functional theory (DFT) calculations. The enantiotopic hydroxyl groups of the meso-diols are clearly differentiated by the stereochemistry at the C2 position of the glycosyl donor with excellent regioselectivities. In addition, the present method is successfully applied to the synthesis of core structures of phosphatidylinositolmannosides (PIMs) and glycosylphosphatidylinositol (GPI) anchors, and common β-mannoside structures of the LLBM-782 series of antibiotics.

display all >>

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

Reviews, Commentaries, etc. 【 Display / hide

  • 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

    Introduction and explanation (scientific journal), Joint Work

  • 架橋構造をもつ糖

    高橋 大介、戸嶋 一敦

    月刊化学 75 ( 2 ) 72 - 73 2020.01

    Introduction and explanation (scientific journal), Joint Work

  • アントラキノン-レクチンハイブリッド分子による標的糖蛋白質の選択的光分解―肝がん関連糖蛋白質AFP-L3の選択的光分解

    高橋 大介、戸嶋 一敦

    週刊医学のあゆみ (医歯薬出版)  269 ( 9 ) 711 - 717 2019.06

    Introduction and explanation (scientific journal), Joint Work

  • Regioselective and Stereoselective Glycosylations Utilizing Organoboron Compounds

    *Daisuke Takahashi, Masamichi Tanaka, *Kazunobu Toshima

    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY 30 ( 174 ) E55 - E62 2018.05

    Introduction and explanation (scientific journal), Single Work,  ISSN  09157352

     View Summary

    © 2018 FCCA (Forum: Carbohydrates Coming of Age) Development of regio- and stereoselective glycosylations leading to a specific hydroxyl group among several free hydroxyl groups is a challenging and long-standing research subject in carbohydrate chemistry. In this context, several efficient regio- and stereoselective glycosylation methods utilizing organoboron reagents, which can bind reversibly to cis-1,2- or 1,3-diols under mild conditions, have been reported. In this focused review article, several organoboron-mediated regio- and stereoselective glycosylations are described, including recently developed methods.

  • Novel 1,2-cis-Stereoselective Glycosylations Utilizing Organoboron Reagents and Their Application to Natural Products and Complex Oligosaccharide Synthesis

    D. Takahashi, M. Tanaka, N. Nishi, K. Toshima

    Carbohydrate Research 452   64 - 77 2017.11

    Introduction and explanation (scientific journal), Joint Work

display all >>

Presentations 【 Display / hide

  • Efficient Synthesis of α-1,3-Glucan Using Boron-Mediated Aglycon Delivery (BMAD) Method

    Shunpei Tomita, Daisuke Takahashi, Kazunobu Toshima

    Efficient Synthesis of α-1,3-Glucan Using Boron-Mediated Aglycon Delivery (BMAD) Method (On line ) , 2021.03, Oral Presentation(general), The Chemical Society of Japan

  • Development of Influenza Virus Sensor Using O-Sialoside-Immobilized Diamond Electrode

    Tatsuki Koike, Hayate Kato, Takashi Yamamoto, Teruhiko Matsubara, Yasuaki Einaga, Toshinori Sato, Daisuke Takahashi, Kazunobu Toshima

    Development of Influenza Virus Sensor Using O-Sialoside-Immobilized Diamond Electrode (On line ) , 2021.03, Oral Presentation(general), The Chemical Society of Japan

  • Structure-Activity Relationship Study of Mannosylerythritol Lipids for the Recovery Effect on the Damaged Cultured Human Skin Cells

    Takanori Kondo, Nobuya Nishi, Tomotake Morita, Daisuke Takahashi, Kazunobu Toshima

    Structure-Activity Relationship Study of Mannosylerythritol Lipids for the Recovery Effect on the Damaged Cultured Human Skin Cells (On line ) , 2021.03, Oral Presentation(general), The Chemical Society of Japan

  • Design, Synthesis and Biological Evaluation of H2O2-Activatable Photosensitizer based on Hypocrellin B

    Takashi Kitamura, Hirotaka Nakata, Daisuke Takahashi, Kazunobu Toshima

    Design, Synthesis and Biological Evaluation of H2O2-Activatable Photosensitizer based on Hypocrellin B (On line ) , 2021.03, Oral Presentation(general), The Chemical Society of Japan

  • Design, Synthesis and Biological Evaluation of Stimuli Activatable Photosensitizer―Fluorophore Hybrids toward Theranostics

    Saori Shiroshita, Daisuke Takahashi, Kazunobu Toshima

    Design, Synthesis and Biological Evaluation of Stimuli Activatable Photosensitizer―Fluorophore Hybrids toward Theranostics (On line ) , 2021.03, Oral Presentation(general), The Chemical Society of Japan

display all >>

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

  • 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, 戸嶋 一敦, 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, 戸嶋 一敦, 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.

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

    Application No.: 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

    Application No.: 特願2010-022168  2009.02 

    Patent, Joint, National application

  • 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

    Application No.: 特願2007-507210  2006.03 

    Registration No.: 特許第5046029号  2012.07

    Patent, Single

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

display all >>

 

Courses Taught 【 Display / hide

  • SEMINAR IN APPLIED CHEMISTRY

    2021

  • MOLECULAR LIFE CHEMISTRY 1

    2021

  • LABORATORIES IN APPLIED CHEMISTRY D

    2021

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2021

  • GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

    2021

display all >>

 

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

display all >>

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

display all >>