Details of a Researcher - Toshima, Kazunobu

Toshima, Kazunobu

写真a

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

Position: Professor

Related Websites

http://www.applc.keio.ac.jp/~toshima/

External Links

Page Top ▲

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 >>

Page Top ▲

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

Page Top ▲

Academic Degrees 【 Display / hide 】

工学　, Keio University, 1988.03

Page Top ▲

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

Page Top ▲

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

display all >>

Page Top ▲

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

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.
- 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

Last author, 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

Last author, 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 （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.
- 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)

display all >>

Page Top ▲

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

Development of hybrid-type photoactivatable bio-functional molecules and its application to chemical biology

Toshima, Kazunobu

福澤諭吉記念慶應義塾学事振興基金事業報告集（福澤基金運営委員会) 2020
Creation of agents that selectively photo-degrade certain proteins and oligosaccharides and its application to control of cell functions

Toshima, Kazunobu

科学研究費補助金研究成果報告書 2016
Creation of novel biofunctional molecules for target-selective photodegradation of proteins and carbohydrates

Toshima, Kazunobu

科学研究費補助金研究成果報告書 2013
Development of designed agents that selectively photo-degrade certain proteins and oligosaccharides

Toshima, Kazunobu

科学研究費補助金研究成果報告書 2010

Page Top ▲

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, 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.
- 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, 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
- 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

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

display all >>

Page Top ▲

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
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
Boronic-acid-catalyzed diastereoselective desymmetric 1,2-cis-Glycosylation of meso-diols via chirality transfer from a glycosyl donor

Daisuke Takahashi, Masamichi Tanaka, Koji Sato, Ryoki Yoshida, Nobuya Nishi, Rikuto Oyamada, Kazuki Inaba, Kazunobu Toshima

The 2021 International Chemical Congress of Pacific Basin Societies,

2021.12
,
Oral presentation (general)

display all >>

Page Top ▲

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.

Page Top ▲

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