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 】

• Organic chemistry (Carbohydrate Chemistry)

• Organic chemistry (Synthetic Organic Chemistry)

• 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 】

• 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

• Green Solvents II: Properties and Applications of Ionic Liquids

  Kaname Sasaki, Daisuke Takahashi, Kazunobu Toshima*, Springer, 2012.03

  Scope: Ionic liquids as green solvents for glycosylation reactions. Chapter 3, pp. 67-78

Papers 【 Display / hide 】

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), Joint Work, 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)

• 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.

  • Access to Document (DOI)

• 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.

  • Access to Document (DOI)

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

  Masamichi Tanaka, Koji Sato, Ryoki Yoshida, Nobuya Nishi, Rikuto Oyamada, Kazuki Inaba, *DAISUKE TAKAHASHI, *Kazunobu Toshima

  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.
  
  This paper was press-released from Keio University. (https://www.keio.ac.jp/ja/press-releases/2020/5/18/28-69846/)
  This paper was highlighted in Nikkei Sangyo Newspaper on September 15, 2020.

  • 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 】

• 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

  • Access to Document (DOI)

• 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

• Regioselective and Stereoselective Glycosylations Utilizing Organoboron Compounds

  *Daisuke Takahashi, Masamichi Tanaka, *Kazunobu Toshima

  TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY (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.

  • Access to Document (DOI)

• Borinic Acid Catalyzed 1,2─cis─Stereoselective Glycosylations and Their Applications to the Total Synthesis of Natural Products

  *Daisuke Takahashi

  Journal of Synthetic Organic Chemistry, Japan (The Society of Synthetic Organic Chemistry, Japan)  76 ( 5 ) 470 - 473 2018.05

  Introduction and explanation (scientific journal), Single Work

  • Access to Document (DOI)

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

  *Daisuke Takahashi, Masamichi Tanaka, Nobuya Nishi, *Kazunobu Toshima

  CARBOHYDRATE RESEARCH (Elsevier)  452 ( 27 ) 64 - 77 2017.10

  Introduction and explanation (scientific journal), Joint Work,  ISSN  0008-6215

  • Access to Document (DOI)

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Presentations 【 Display / hide 】

Presentations 【 Display / hide 】

• Regioselective and 1,2-cis-stereoselective glycosylations realized by organoboron catalysts

  Daisuke Takahashi

  日本薬学会第140年会 (京都、国立京都国際会館) , 2020.03, Oral Presentation(guest/special), 日本薬学会

• Synthetic Study on Kanamycin B: Application of Diastereoselective Desymmetric 1,2-cis-Glycosylation

  Koji Sato, Masamichi Tanaka, Rikuto Oyamada, Daisuke Takahashi, Kazunobu Toshima

  日本化学会第100春季年会 (東京理科大学 野田キャンパス) , 2020.03, Oral Presentation(general), 日本化学会

• Synthesis of a Fucoidan Derivative and Its Inhibitory Activities toward Heparanase and Hyaluronidase

  Yuko Kanno, Sumika Komaba, Daisuke Takahashi, Kazunobu Toshima

  日本化学会第100春季年会 (東京理科大学 野田キャンパス) , 2020.03, Oral Presentation(general), 日本化学会

• Synthesis of Oligosaccharide derived from Pathogenic E. coli Using Boronic-Acid-Catalyzed Regio- and Stereoselective β-Rhamnosylation

  Nobuya Nishi, Katsunori Seki, Daisuke Takahashi, Kazunobu Toshima

  日本化学会第100春季年会 (東京理科大学 野田キャンパス) , 2020.03, Oral Presentation(general), 日本化学会

• Synthetic Study on a Natural Glycosphingolipid, Terpioside B

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

  日本化学会第100春季年会 (東京理科大学 野田キャンパス) , 2020.03, Oral Presentation(general), 日本化学会

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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, 高橋 大介, 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, 高橋　大介, 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, 高橋　大介, 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 】

• 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： Awards of National Conference, Council and Symposium

• 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： Awards of National Conference, Council and Symposium

• 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： Awards of National Conference, Council and Symposium

• 2015 GlycoTOKYO Incentive Award

  2015.10, GlycoTOKYO, Target-Selective Synthesis and Photodegradation of Oligosaccharides Utilizing Organoboron Compounds

• Kaneka Corporation Award in Synthetic Organic Chemistry,　Japan

  TAKAHASHI Daisuke, 2015.02, The Society of Synthetic Organic Chemistry, Japan, Development and Application of Regio- and Stereoselective and Environmentally Benign Glycosylation Using a Boronic Acid-Glycosyl Acceptor Ester Catalyst

  Type of Award： Awards of National Conference, Council and Symposium

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Courses Taught 【 Display / hide 】

Courses Taught 【 Display / hide 】

• SEMINAR IN APPLIED CHEMISTRY

  2021

• MOLECULAR LIFE CHEMISTRY 2

  2021

• LABORATORY IN SCIENCE

  2021

• LABORATORIES IN APPLIED CHEMISTRY D

  2021

• INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

  2021

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Courses Previously Taught 【 Display / hide 】

Courses Previously Taught 【 Display / hide 】

• Molecular Life Chemistry 1

  Keio University, 2018, Autumn Semester, Major subject, Lecture, Within own ｆaculty, 1h

• Molecular Life Chemistry 2

  Keio University, 2018, Autumn Semester, Major subject, 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

• GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

  Keio University, 2018

• GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 1

  Keio University, 2018

• INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

  Keio University, 2018

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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 】

• 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

• 2016.07

  -

  2017.07

  実行委員, 第52回天然物化学談話会

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