Details of a Researcher - Takahashi, Daisuke

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

https://www.applc.keio.ac.jp/~toshima/takahashi_Eng.pdf

Contact Address: 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa

External Links

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

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 】

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

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 】

Carbohydrate Chemistry
Synthetic Organic Chemistry
Glycosylation Reaction
Chemical Biology
Glycosylated Natural Products

Books 【 Display / hide 】

Modern Natural Product Synthesis -Overcoming Difficulties

*DAISUKE TAKAHASHI, *Kazunobu Toshima, Springer Nature, 2024.05, Page： 20

Scope: Complex Oligosaccharides Synthesis—Challenges and Tactics, Contact page： 299-318 , Accepted
Comprehensive Glycoscience: Second Edition

*DAISUKE TAKAHASHI, *Kazunobu Toshima, Elsevier, 2021.06, Page： 48

Scope: 1,2-cis O-Glycosylation Methods, Contact page： 365-412 , Accepted
- Access to Document (DOI)
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.

Papers 【 Display / hide 】

Designed Mannosylerythritol Lipid Analogues Exhibiting both Selective Cytotoxicity against Human Skin Cancer Cells and Recovery Effects on Damaged Skin Cells

Jikun Meng, Chihiro Yasui, Mai Shida, Kazunobu Toshima, *DAISUKE TAKAHASHI

Chemistry A European Journal 2024.05

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted
- Access to Document (DOI)
Photo-Induced Glycosylation Using the Edible Polyphenol Curcumin

Satomi Goi, Hidenari Shigeta, DAISUKE TAKAHASHI, *Kazunobu Toshima

（Organic & Biomolecular Chemistry) 2024.05

Research paper (scientific journal), Accepted
- Access to Document (DOI)
Discovery of a Novel Photosensitizer Based on the Enediyne Antibiotic N1999A2 and Its Application as a Glutathione-Activatable Theranostic Agent

Kotono Matsunaga, Minami Takahashi, Tugumi Kagaya, DAISUKE TAKAHASHI, *Kazunobu Toshima

Bulletin of the Chemical Society of Japan 97 （ 5 ） uoae057 2024.05

Research paper (scientific journal), Joint Work, Accepted
- Access to Document (DOI)
Synthesis and Immunological Evaluation of Escherichia coli O1- Derived Oligosaccharide–Protein Conjugates toward Avian Pathogenic Escherichia coli O1 Vaccine Development

Katsunori Seki, Takumi Makikawa, *Kazunobu Toshima, *DAISUKE TAKAHASHI

Synthesis （Georg Thieme Verlag KG) 56 （ 06 ） 953 - 965 2023.08

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted, ISSN 0039-7881

　View Summary

Abstract

Avian pathogenic Escherichia coli O1 (APEC O1) is a pathogenic bacterium that causes significant economic losses in the poultry industry and raises concerns about zoonotic infections. The development of effective vaccines against APEC O1 is essential due to antibiotic resistance and the potential for severe symptoms in both chickens and humans. In this context, we have been focusing on the O1A, O1B, and O1C antigen structures derived from E. coli O1 lipopolysaccharide (LPS). In this study, the first synthesis of the pentasaccharide repeating units of the O1B and O1C antigens was successfully achieved. The synthesis and immunological evaluation of their conjugates with bovine serum albumin (BSA) were conducted. Only the O1A-pentasaccharide structure is a glycotope candidate for APEC O1. Keyhole limpet hemocyanin (KLH)–O1A-pentasaccharide conjugate was also synthesized, and its immunogenicity was evaluated by the ELISA assay. The efficient production of antibodies capable of binding to both APEC O1 LPS and the O1A-pentasaccharide structure was observed, indicating that O1A-pentasaccharide is a promising vaccine candidate against APEC O1.
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.
- Access to Document (DOI)

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

Pathogen sensor based on boron-doped diamond (BDD) electrode terminated with biologically active carbohydrates

Takahashi, Daisuke

学事振興資金研究成果実績報告書（慶應義塾大学) 2020
Pathogen sensor based on boron-doped diamond (BDD) electrode terminated with biologically active carbohydrates

Takahashi, Daisuke

学事振興資金研究成果実績報告書（慶應義塾大学) 2019
Synthetic and structure-activity relationship studies on a natural glycolipid, terpioside B

Takahashi, Daisuke

学事振興資金研究成果実績報告書（慶應義塾大学) 2018
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

Reviews, Commentaries, etc. 【 Display / hide 】

Total Synthesis of Mannosylerythritol Lipids and Structure-Function Relationship Studies

*DAISUKE TAKAHASHI, Kazunobu Toshima

Journal of Oleo Science 73 ( 4 ) 539 - 546 2024.04

Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Lead author, Corresponding author
Photo-Induced Glycosylations Using Organophotoacids: A New Environmentally Benign Carbohydrate Synthesis

*Kazunobu Toshima, DAISUKE TAKAHASHI, Yuka Isozaki

Synlett 35 777 - 788 2023.07

Article, review, commentary, editorial, etc. (scientific journal), Joint Work
有機化学を基盤とした鳥類病原性大腸菌に対する複合糖質ワクチン開発への挑戦

<u>高橋大介</u>

日生研たより 69 ( 2 ) 3 - 11 2023.04

Article, review, commentary, editorial, etc. (scientific journal), Single Work, Lead author, Last author, Corresponding author
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
- Access to Document (DOI)
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)

Presentations 【 Display / hide 】

ホウ素媒介アグリコン転移反応を用いたアレルギー抑制活性糖質の創製研究

内藤優奈, 稲葉和樹, 立花実奈, 戸嶋一敦, 高橋大介

日本化学会第104春季年会（2024）,

2024.03
,
Oral presentation (general)
エンジイン系抗生物質N1999A2を基本骨格としたがん細胞応答型光感受性分子の創製

加賀谷つぐみ, 高橋南美, 松永ことの, 高橋大介, 戸嶋一敦

日本化学会第104春季年会（2024） (日本大学理工学部船橋キャンパス) ,

2024.03
,
Oral presentation (general)
可食性ポリフェノールクルクミンを活性化剤に用いたN-光グリコシル化反応の開発

五井里美、高橋大介、戸嶋一敦

日本化学会第104春季年会（2024） (日本大学理工学部船橋キャンパス) ,

2024.03
,
Oral presentation (general)
セラノスティクスを指向したがん細胞応答型光感受性分子―蛍光分子ハイブリッドの創製

松永ことの, 髙橋南美, 加賀谷つぐみ, 高橋大介, 戸嶋一敦

日本化学会第104春季年会（2024） (日本大学理工学部船橋キャンパス) ,

2024.03
,
Oral presentation (general)
マンノシルエリスリトールリピッド類の全合成と機械学習による抗菌活性予測モデルの構築

志田真愛, 安井ちひろ, 澁谷優子, 林千草, 五十嵐雅之, 飛田春香, 緒明佑哉, 戸嶋一敦, 高橋大介

GlycoTOKYO2023 (慶應義塾大学日吉キャンパス) ,

2023.12
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Poster presentation, 東京糖鎖研究会

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

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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

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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

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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

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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

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2023.03

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

Intellectual Property Rights, etc. 【 Display / hide 】

新規な抗生物質及びその製造方法

Date applied：特願2023- 90620 2023.06

Patent, Joint
抗腫瘍剤

Date applied：特願2014-140761 2014.07

Date announced：特開2015-38061 2015.02

Date issued：特許6403317 2018.10

Date registered： 2018.09

Patent, Single
ノイラミニダーゼに対する酵素阻害剤

Date applied：特願2010-022168 2010.02

Date announced：特開2011-157325 2011.08

Patent, Joint
糖鎖アレイ及びその製造方法

Date applied：特願2004-264922 2004.09

Date announced：特開2006-78418 2006.03

Patent
Ｎ-グリコシルアミドの製造方法

Date applied：特願2003-436790 2003.12

Date announced：特開2005-187441 2005.07

Patent, Single

Awards 【 Display / hide 】

2023 Asian Core Program Lectureship Award

DAISUKE TAKAHASHI, 2023.12, The Organizing Committee of the 16th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-16), Efficient Synthesis of Biologically Active Glycosides by Boron-Mediated Aglycon Delivery and Their Applications in Chemical Biology

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

Courses Taught 【 Display / hide 】

SEMINAR IN APPLIED CHEMISTRY

2024
MOLECULAR LIFE CHEMISTRY 2

2024
LABORATORY IN SCIENCE

2024
LABORATORIES IN APPLIED CHEMISTRY D

2024
INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

2024

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
BACHELOR'S THESIS

Keio University

2018.04

-

2019.03
,
Full academic year
SEMINAR IN APPLIED CHEMISTRY

Keio University

2018.04

-

2019.03
,
Full academic year
生体物質化学基礎

Keio University

2018.04

-

2019.03
,
Autumn Semester, Lecture, Within own ｆaculty, 1h, 161people

Memberships in Academic Societies 【 Display / hide 】

Japan Oil Chemists' Society, member,

2018.06

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Present
American Chemical Society, member,

2017.11

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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

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Present
有機合成化学協会、会員,

2005

-

Present

Committee Experiences 【 Display / hide 】

2023.07

-

2024.06

日本学術振興会特別研究員等審査会専門委員, 独立行政法人　日本学術振興会
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)