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

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Career 【 Display / hide 】

1988.04

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1989.03

ペンシルバニア大学化学科 ,博士研究員
1989.04

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1994.03

慶應義塾大学（理工学部） ,助手
1994.04

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1996.03

慶應義塾大学（理工学部） ,専任講師
1996.04

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2003.03

慶應義塾大学理工学部（応用化学科）,助教授
1997.04

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1999.03

慶應義塾大学理工学応用化学科教室幹事

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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

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Academic Degrees 【 Display / hide 】

工学　, Keio University, 1988.03

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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

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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
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

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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), 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

Last author, Corresponding author, 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卷（ 5号） uoae057頁 2024.05

Research paper (scientific journal), Last author, Corresponding author, 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巻（ 06号） 953頁 - 965頁 2023.08

Research paper (scientific journal), Joint Work, 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

Joint Work, 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.
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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) 2022
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) 2021
Development of stimuli activatable photosensitizers and its application to control of cell function

Toshima, Kazunobu

学事振興資金研究成果実績報告書（慶應義塾大学) 2021
Development of stimuli activatable photosensitizers and its application to control of cell function.

Toshima, Kazunobu

学事振興資金研究成果実績報告書（慶應義塾大学) 2020
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

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Reviews, Commentaries, etc. 【 Display / hide 】

Total Synthesis of Mannosylerythritol Lipids and Structure-Function Relationship Studies

*DAISUKE TAKAHASHI, Kazunobu Toshima

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

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

*Kazunobu Toshima, DAISUKE TAKAHASHI, Yuka Isozaki

Synlett 35卷 777頁 - 788頁 2023.07

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

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Presentations 【 Display / hide 】

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
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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
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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
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Oral presentation (general)
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
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Oral presentation (general)
可食性ポリフェノールエラグ酸を活性化剤に用いた光グリコシル化反応の開発

重田英就, 五井里美, 高橋大介, 戸嶋一敦

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

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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

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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

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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

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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.

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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