KEIO RESEARCHERS INFORMATION SYSTEM

Career 【 Display / hide 】

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 】

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

Academic Degrees 【 Display / hide 】

Academic Degrees 【 Display / hide 】

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

Research Areas 【 Display / hide 】

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

Research Keywords 【 Display / hide 】

Research Keywords 【 Display / hide 】

• Carbohydrate Chemistry

• Synthetic Organic Chemistry

• Glycosylation Reaction

• Chemical Biology

• Glycosylated Natural Products

Books 【 Display / hide 】

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.

• 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 】

Papers 【 Display / hide 】

• 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

  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.

  • Access to Document (DOI)

• Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H2O2-expressing cancer cells.

  Takashi Kitamura, Hirotaka Nakata, Daisuke Takahashi, Kazunobu Toshima

  Chemical communications (Cambridge, England) （Chemical Communications)  58 （ 2 ） 242 - 245 2022.01

  Corresponding author, Accepted,  ISSN  13597345

  　View Summary

  A novel tumor-related biomarker, a H2O2-activatable photosensitizer 4 based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer 4 showed a blue-shifted absorption band compared with 3, and showed negligible photosensitizing ability without H2O2. However, the release of 3 from 4 by the reaction with H2O2 regenerated the photosensitizing ability. Furthermore, 4 exhibited selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.

  • Access to Document (DOI)

• Synthesis of low-molecular weight fucoidan derivatives and their binding abilities to SARS-CoV-2 spike proteins

  Tatsuki Koike, Aoi Sugimoto, Shuhei Kosono, Sumika Komaba, Yuko Kanno, Takashi Kitamura, Itsuki Anzai, Tokiko Watanabe, Daisuke Takahashi, Kazunobu Toshima

  RSC Medicinal Chemistry （Royal Society of Chemistry (RSC))  12 （ 12 ） 2016 - 2021 2021.12

  Corresponding author, Accepted,  ISSN  26328682

  　View Summary

  Synthesized fucoidan derivative 10 exhibited inhibitory activities against the binding of heparin with several SARS-Cov-2 spike proteins, but did not inhibit factor Xa activity that could otherwise lead to undesirable anticoagulant activity.

  • Access to Document (DOI)

• 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 （Wiley)  60 （ 4 ） 1789 - 1796 2021.01

  Research paper (scientific journal), Joint Work, Corresponding author, 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.

  • Access to Document (DOI)

• 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.

  • Access to Document (DOI)

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

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

• Development and application of regio- and stereoselective beta-mannosylation utilizing organoboron reagents

  Takahashi, Daisuke

  科学研究費補助金研究成果報告書 2018

• Creation of artificial functional lectins for target-selective labeling of carbohydrates and their application to cell surface engineering

  Takahashi, Daisuke

  科学研究費補助金研究成果報告書 2015

• Design and synthesis of artificial receptors for disease-related oligosaccharides, and their applications for controlling cell functions

  Takahashi, Daisuke

  科学研究費補助金研究成果報告書 2011

Reviews, Commentaries, etc. 【 Display / hide 】

Reviews, Commentaries, etc. 【 Display / hide 】

• 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.

  • Access to Document (DOI)

• 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

• 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

  • Access to Document (DOI)

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Presentations 【 Display / hide 】

Presentations 【 Display / hide 】

• Photo-Degradation of Proteins and Photocytotoxicity by Naphthol Derivatives of Enediyne Antibiotics

  Minami Takahashi;Kotono Matsunaga;Takashi Kitamura;Daisuke Takahashi;Kazunobu Toshima

  The 16th Annual Meeting of Japanese Society for Chemical Biology, 

  2022.05

  -

  2022.06

  , 

  Poster presentation

• 有機化学を基盤とした新興感染症に対する阻害剤および複合糖質ワクチンの開発研究

  Daisuke Takahashi

  一般財団法人 日本生物科学研究所 第二研究会, 

  2022.04

  , 

  Public lecture, seminar, tutorial, course, or other speech

• Synthesis of Oligosaccharide Derived from Pathogenic Escherichia Coli O1‒Protein Conjugates and Identification of a Glycotope of Avian Pathogenic Escherichia Coli O1

  Katsunori Seki, Takumi Makikawa, Daisuke Takahashi, Kazunobu Toshima

  The 102th CSJ Annual Meeting (2022), 

  2022.03

  , 

  Oral presentation (general)

• Synthesis of Mannosylerythritol Lipid Derivatives and Their Recovery Effects on the Damaged Cultured Human Skin Cells

  Chihiro Yasui, Takanori Kondo, Tomotake Morita, Daisuke Takahashi, Kazunobu Toshima

  The 102th CSJ Annual Meeting (2022), 

  2022.03

  , 

  Oral presentation (general)

• First total synthesis of glycosphingolipids, terpioside B

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

  The 2021 International Chemical Congress of Pacific Basin Societies, 

  2021.12

  , 

  Poster presentation

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

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

• 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

  -

  Present

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

• 有機ホウ素分子を活用した位置及び立体選択的β-マンノシル化反応の開発と応用

  2016.04

  -

  2019.03

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

• Creation of artificial functional lectins for target-selective labeling of carbohydrates and their application to cell surface engineering

  2013.04

  -

  2016.03

  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Daisuke Takahashi, Grant-in-Aid for Young Scientists (B), Research grant, Principal investigator

• Design and synthesis of artificial receptors for disease-related oligosaccharides, and their applications for controlling cell functions

  2010.04

  -

  2012.03

  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Daisuke Takahashi, Grant-in-Aid for Young Scientists (B), Research grant, Principal investigator

Awards 【 Display / hide 】

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 】

Courses Taught 【 Display / hide 】

• SEMINAR IN APPLIED CHEMISTRY

  2022

• MOLECULAR LIFE CHEMISTRY 2

  2022

• LABORATORY IN SCIENCE

  2022

• LABORATORIES IN APPLIED CHEMISTRY D

  2022

• INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

  2022

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Courses Previously Taught 【 Display / hide 】

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

• GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

  Keio University

  2018.04

  -

  2019.03

• GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 1

  Keio University

  2018.04

  -

  2019.03

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Memberships in Academic Societies 【 Display / hide 】

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 】

Committee Experiences 【 Display / hide 】

• 2021.03

  -

  Present

  日本化学会関東支部役員（幹事）, 日本化学会

• 2018.12

  -

  2019.05

  第7回慶應有機化学若手シンポジウム実行委員, 慶應有機化学若手シンポジウム実行委員会

• 2018.12

  -

  2019.05

  第77回関東支部シンポジウム実行委員, 第77回関東支部シンポジウム実行委員会

• 2017.12

  -

  2018.05

  第６回慶應有機化学若手シンポジウム実行委員, 慶應有機化学若手シンポジウム実行委員会

• 2016.12

  -

  2017.04

  第５回慶應有機化学若手シンポジウム実行委員, 慶應有機化学若手シンポジウム実行委員会

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