Papers - Takahashi, Daisuke

Total Synthesis of Kanamycins

Kanae Hosomi, Banjo Imai, Naoto Takemura, Kazuki Senoo, Chigusa Hayashi, Masayuki Igarashi,*Kazunobu Toshima, *DAISUKE TAKAHASHI

CHEMISTRY-A EUROPEAN JOURNAL (Wiley-VCH)     e202500685 (9 pages) 2025.04

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

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Stereoselective Total Synthesis of α-Galacto-OligosaccharidesUsing Boron-Mediated Aglycon Delivery and Evaluation of their Immune-Enhancing Activities

Jikun Meng, Moeri Sagawa, *Kazunobu Toshima, *DAISUKE TAKAHASHI

CHEMBIOCHEM (Wiley-VCH)  26   e202401059 (6 pages) 2025.04

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

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Photo-induced glycosylation using edible polyphenol ellagic acid

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

CARBOHYDRATE RESEARCH (Elsevier)  552   109461 (6 pages) 2025.03

Research paper (scientific journal), Joint Work, Accepted

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Creation of a New Macrolide Antibiotic against Non-tuberculous Mycobacterium Using Late-stage Boron-mediated Aglycon Delivery

Yuka Isozaki, Takumi Makikawa, Kosuke Kimura, Daiki Nishihara, Fujino, Yoshikazu Tanaka, Chigusa Hayashi, Yoshimasa Ishizaki, *Masayuki Igarashi, *Takeshi Yokoyama, *Kazunobu Toshima, *DAISUKE TAKAHASHI

SCIENCE ADVANCES (American Association for the Advancement of Science)  11 ( 10 ) eadt2352 (12 pages) 2025.03

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

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A novel porphyrin-based theranostic agent activated by cysteine over-expressed in cancer cells shows promise for tumour-targeted monitoring and phototherapy

Fumihisa Ishida, Satoe Moriya, DAISUKE TAKAHASHI, *Kazunobu Toshima

BIOORGANIC & MEDICINAL CHEMISTRY (Elsevier)  121   118131 (9 pages) 2025.02

Research paper (scientific journal), Joint Work, Accepted

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Synthesis of Low-Molecular-Weight Fucoidan Analogue and Its Inhibitory Activities against Heparanase and SARS-CoV-2 Infection

Aoi Sugimoto, Tatsuki Koike, Yuya Kuboki, Sumika Komaba, Shuhei Kosono, Maniyamma Aswathy, Itsuki Anzai, Tokiko Watanabe, *Kazunobu Toshima, *DAISUKE TAKAHASHI

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley-VCH)  64 ( 6 ) e202411760 (7 pages) 2024.10

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

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A novel photosensitizer based on hypocrellin B activated by cysteine over-expressed in cancer cells

Fumihisa Ishida, Rikuto Onishi, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  22   7187 - 7193 2024.08

Research paper (scientific journal), Joint Work, Accepted

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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 (Wiley-VCH)  30   e202401319 (7 pages) 2024.05

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

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Photo-Induced Glycosylation Using the Edible Polyphenol Curcumin

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

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  22   5546 - 5551 2024.05

Research paper (scientific journal), Accepted

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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 (Chemical Society of Japan)  97 ( 5 ) uoae057 (9 pages) 2024.05

Research paper (scientific journal), Joint Work, Accepted

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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

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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-VCH)  62 ( 46 ) e202307015 (10 pages) 2023.07

Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted,  ISSN  14337851

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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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Photoinduced Glycosylation Using a Diarylthiophene as an Organo Lewis Photoacid Catalyst

Naoki Otani, Kohei Higashiyama, Hayato Sakai, Taku Hasobe, *DAISUKE TAKAHASHI, *Kazunobu Toshima

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (Wiley-VCH)  26 ( 20 ) e202300287 (6 pages) 2023.04

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1434193X

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Here reports an photoinduced glycosylation of trichloroacetimidate donors and several alcohols using 3,11-dimethoxydinaphthothiophene as an organo Lewis photoacid catalyst upon long-wavelength UV-LED light (385 nm) irradiation. The reaction proceeded under mild reaction conditions smoothly to give the corresponding glycosides in good to high yields. In addition, the present glycosylation method was applicable to a wide range of trichloroacetimidate donors and acceptors. Furthermore, the dinaphthothiophene catalyst could be recovered and reused without any loss of efficiency. Moreover, this glycosylation method was applied successfully to the total synthesis of a biologically active natural product, cholesteryl 6-O-myristoyl-α-glucoside.

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Destabilization of vitelline membrane outer layer protein 1 homolog (VMO1) by C‐mannosylation

Satoshi Yoshimoto, Takehiro Suzuki, Naoki Otani, DAISUKE TAKAHASHI, Kazunobu Toshima, Naoshi Dohmae, *Siro Simizu

FEBS OPEN BIO (Wiley-VCH)  13 ( 3 ) 490 - 499 2023.01

Joint Work, Accepted,  ISSN  2211-5463

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Synthesis of Mannosylerythritol Lipid Analogues and their Self-Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity.

Takanori Kondo, Chihiro Yasui, Ikkei Miyajima, Taisuke Banno, Kouichi Asakura, Tokuma Fukuoka, Kazunori Ushimaru, Maito Koga, Azusa Saika, Tomotake Morita, Yoshiaki Takahashi, Chigusa Hayashi, Masayuki Igarashi, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY-A EUROPEAN JOURNAL (Wiley-VCH)  28 ( 55 ) e202201733 (7 pages) 2022.10

Corresponding author, Accepted,  ISSN  09476539

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Synthesis of three types of purpose-designed mannosylerythritol lipid (MEL)-D analogues with decanoyl groups (C10), β-GlcEL-D, α-GlcEL-D, and α-MEL-D, was accomplished utilizing our boron-mediated aglycon delivery (BMAD) methods. Their self-assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. It was revealed, for the first time, that α-GlcEL-D and α-MEL-D only generated giant vesicles, indicating that slight differences in the steric configuration of an erythritol moiety and fatty acyl chains affect the ability to form vesicles. Analogue α-MEL-D exhibited significant recovery effects on damaged skin cells. Furthermore, α-MEL-D exhibited antibacterial activity as high as that for MEL-D, indicating that α-MEL-D is a promising artificial sugar-based material candidate for enhancing the barrier function of the stratum corneum, superior to a known cosmetic ingredient, and possesses antibacterial activity.

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Efficient Strategy for the Preparation of Chemical Probes of Biologically Active Glycosides Using a Boron-Mediated Aglycon Delivery (BMAD) Method

Kosuke Kimura, Takeshi Yasunaga, Takumi Makikawa, *DAISUKE TAKAHASHI, *Kazunobu Toshima

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (The Chemical Society of Japan)  95 ( 7 ) 1075 - 1082 2022.07

Joint Work, Corresponding author, Accepted,  ISSN  00092673

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Development of an efficient method for the analysis and identification of the target proteins with which biologically active glycosides directly interact is highly desirable in many research fields. In this article, we report an efficient strategy for the preparation of chemical probes of biologically active glycosides using a reaction sequence of i) a boron-mediated aglycon delivery (BMAD) with an N3-functionalized 1,2-anhydroglu-cose donor, ii) deprotection, and iii) strain-promoted azidealkyne cycloaddition. Using the synthesized chemical probes, we successfully demonstrated that the target proteins of a cardiac glycoside, lanatoside C (1), can be visualized and identified in human colon cancer HCT116 cells.

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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 (Wiley-VCH)  23 ( 2 ) e202100631 (6 pages) 2022.01

Joint Work, Corresponding author, Accepted,  ISSN  14394227

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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.

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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 (Royal Society of Chemistry )  58 ( 2 ) 242 - 245 2022.01

Joint Work, Corresponding author, Accepted,  ISSN  13597345

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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.

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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 )  12 ( 12 ) 2016 - 2021 2021.12

Joint Work, Corresponding author, Accepted,  ISSN  26328682

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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.

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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-VCH)  60 ( 4 ) 1789 - 1796 2021.01

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  14337851

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© 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.

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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, Corresponding author, Accepted

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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.

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2-Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein-Photodegrading Agent and Its Application as a H2O2-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, Corresponding author, Accepted,  ISSN  09476539

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© 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.

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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, Corresponding author, Accepted,  ISSN  09476539

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© 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.

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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, Corresponding author, Accepted

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© 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.

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Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi, Takahiro Eto, Manabu Aoyagi, Reiji Kurinami, Hayato Sakai, Taku Hasobe, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (The Royal Society of Chemistry)  18 ( 5 ) 851 - 855 2020.01

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  14770520

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© 2020 The Royal Society of Chemistry. Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

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Total Synthesis and Structure–Activity Relationship Study of Vineomycin A₁

Yuka Matsumoto, Hajime Kuriki, Takashi Kitamura, *DAISUKE TAKAHASHI, *Kazunobu Toshima

THE JOURNAL OF ORGANIC CHEMISTRY (American Chemical Society)  84 ( 22 ) 14724 - 14732 2019.10

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

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The first total synthesis of vineomycin A1 (1) has been accomplished. Structure–activity relationship studies for cytotoxicity against human breast cancer MCF-7 cells using several synthetic vineomycin A1 analogues differing in the number and position of glycon moieties revealed that the cytotoxicity increased as the number of glycon moieties increased. The position of the glycon moiety was one of the key factors for the cytotoxicity of 1. Moreover, in vitro analysis of the cytotoxicity of 1 against MCF-7 cells indicated for the first time that 1 effectively induced cancer cell death by apoptosis, not by acting as a DNA intercalating agent.

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2-Phenylquinoline—Sugar Hybrids as Photo-switchable α-Glucosidase Inhibitors

Takashi Kitamura, Mai Okuyama, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY AN ASIAN JOURNAL (Wiley‐VCH)  14 ( 9 ) 1409 - 1412 2019.03

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  18614728

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Purpose-designed 2-phenylquinoline (PQ)-sugar hybrids 1 and 2 were synthesized and evaluated for their photodegradation activities against an α-glucosidase target. The results indicated that PQ-mannose hybrid 2 selectively and effectively photodegraded α-glucosidase and significantly inhibited its enzymatic activity upon irradiation with long-wavelength UV light in the absence of any additives under neutral and aqueous conditions. Furthermore, 2 selectively and effectively inhibited α-glucosidase activity only with photo-irradiation even in complex cell lysate.

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An Anthraquinone—Enzyme—Peptide Hybrid as a Photo-Switchable Enzyme

Shota Sotokawa, Takashi Kitamura, DAISUKE TAKAHASHI, *Kazunobu Toshima^a

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  54 ( 75 ) 10614 - 10617 2018.08

Research paper (scientific journal), Joint Work, Accepted

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Stereospecific β-L-Rhamnopyranosylation through an S_Ni-Type Mechanism by Using Organoboron Reagents

Nobuya Nishi, Kazuhiro Sueoka, Kiyoko Iijima, Ryuichi Sawa, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  57 ( 42 ) 13858 - 13862 2018.08

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  14337851

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© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Stereospecific β-l-rhamnopyranosylations were conducted using a 1,2-anhydro-l-rhamnopyranose donor and mono-ol or diol acceptors in the presence of a glycosyl-acceptor-derived borinic or boronic ester. Reactions proceeded smoothly to provide the corresponding β-l-rhamnopyranosides (β-l-Rhap) with complete stereoselectivity in moderate to high yields without any further additives under mild conditions. Mechanistic studies of the borinic ester mediated glycosylation using 13C kinetic isotope effect (KIE) measurements and DFT calculations were consistent with a concerted SNi mechanism with an exploded transition state. In addition, the present glycosylation method was applied successfully to the synthesis of a trisaccharide, α-l-Rhap-(1,2)-β-l-Rhap-(1,4)-Glcp, derived from Streptococcus pneumoniae serotypes 7B, 7C, and 7D.

This paper was press-released from Keio University. (https://www.keio.ac.jp/ja/press-releases/2018/8/31/28-47621/)
This paper was highlighted as a Spotlight-Research in Chem-Station.

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Novel hemagglutinin-binding sulfated oligofucosides and their effect on influenza virus infection

Shuhei Kosono, Akihiro Kasai, Sumika Komaba, Teruhiko Matsubara, Toshinori Sato, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  54 ( 54 ) 7467 - 7470 2018.06

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  13597345

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© 2018 The Royal Society of Chemistry. Among a series of chemically synthesized fucoidan derivatives (1-9), 5 was found for the first time to bind to influenza virus hemagglutinins (HAs) and inhibit hemagglutination activity. In addition, a designed C3-symmetric tripodal ligand 10, synthesized with three sulfated oligofucoside moieties of 5, exhibited much greater hemagglutination inhibition activity than 5. A plaque assay using MDCK cells demonstrated that 10 effectively inhibited influenza virus infection.

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Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

Junki Nashida, Nobuya Nishi, Yoshiaki Takahashi, Chigusa Hayashi, Masayuki Igarashi, *DAISUKE TAKAHASHI, *Kazunobu Toshima

THE JOURNAL OF ORGANIC CHEMISTRY (American Chemical Society)  83 ( 13 ) 7281 - 7289 2018.03

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  0022-3263

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© 2018 American Chemical Society. The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

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Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via S_Ni-Type Mechanism

Masamichi Tanaka, Akira Nakagawa, Nobuya Nishi, Kiyoko Iijima, Ryuichi Sawa, *DAISUKE TAKAHASHI, *Kazunobu Toshima

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (American Chemical Society)  140 ( 10 ) 3644 - 3651 2018.02

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1520-5126

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© 2018 American Chemical Society. Regio- and 1,2-cis-stereoselective chemical glycosylation of unprotected glycosyl acceptors has been in great demand for the efficient synthesis of natural glycosides. However, simultaneously regulating these selectivities has been a longstanding problem in synthetic organic chemistry. In nature, glycosyl transferases catalyze regioselective 1,2-cis-glycosylations via the SNi mechanism, yet no useful chemical glycosylations based on this mechanism have been developed. In this paper, we report a highly regio- and 1,2-cis-stereoselective SNi-type glycosylation of 1,2-anhydro donors and unprotected sugar acceptors using p-nitrophenylboronic acid (10e) as a catalyst in the presence of water under mild conditions. Highly controlled regio- and 1,2-cis-stereoselectivities were achieved via the combination of boron-mediated carbohydrate recognition and the SNi-type mechanism. Mechanistic studies using the KIEs and DFT calculations were consistent with a highly dissociative concerted SNi mechanism. This glycosylation method was applied successfully to the direct glycosylation of unprotected natural glycosides and the efficient synthesis of a complex oligos

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Target-Selective Fluorescence Imaging and Photo-Cytotoxicity against H₂O₂ High-Expressing Cancer Cells Using a Photoactivatable Theranostic Agent

Ryoma Takagi, Ayano Takeda, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY AN ASIAN JOURNAL (Wiley‐VCH)  12 ( 20 ) 2656 - 2659 2017.08

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1861-4728

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Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

Nobuya Nishi, Junki Nashida, Eisuke Kaji, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  53 ( 21 ) 3018 - 3021 2017.02

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1359-7345

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Total Synthesis of Aquayamycin

Shunichi Kusumi, Harunobu Nakayama, Takumi Kobayashi, Hajime Kuriki, Yuka Matsumoto, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY-A EUROPEAN JOURNAL (Wiley‐VCH)  22 ( 52 ) 18733 - 18736 2016.11

Research paper (scientific journal), Joint Work, Accepted,  ISSN  0947-6539

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1,2-cis-α-Stereoselective Glycosylation Utilizing a Glycosyl-Acceptor-Derived Borinic Ester and Its Application to the Total Synthesis of Natural Glycosphingolipids

Masamichi Tanaka, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC LETTERS (American Chemical Society)  18 ( 19 ) 5030 - 5033 2016.09

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1523-7060

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Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid

Tomoya Kimura, Takahiro Eto, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC LETTERS (American Chemical Society)  18 ( 13 ) 3190 - 3193 2016.06

Research paper (scientific journal), Joint Work, Accepted,  ISSN  1523-7060

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Target-selective photo-degradation of a sialyl Lewis A (sLe^a) conjugate and photo-cytotoxicity against sLe^a positive cancer cells using an anthraquinone-antibody hybrid

DAISUKE TAKAHASHI, Takashi Nagao, Shota Sotokawa, *Kazunobu Toshima

MED. CHEM. COMMUN. (Royal Society of Chemistry)  7 ( 6 ) 1224 - 1228 2016.05

Research paper (scientific journal), Joint Work, Lead author, Accepted,  ISSN  2040-2503

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Glycosyl-acceptor-derived borinic ester-promoted direct and β-stereoselective mannosylation with a 1,2-anhydromannose donor

Masamichi Tanaka, Junki Nashida, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC LETTERS (American Chemical Society)  18 ( 9 ) 2288 - 2291 2016.05

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

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Target-selective photo-degradation of AFP-L3 and selective photo-cytotoxicity against HuH-7 hepatocarcinoma cells using an anthraquinone-PhoSL hybrid

Mai Okuyama, Haruna Ueno, Yuka Kobayashi, Hirokazu Kawagishi, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  52 ( 10 ) 2169 - 2172 2015.12

Research paper (scientific journal), Joint Work, Accepted,  ISSN  1359-7345

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Glycosylations of glycals using N-iodosuccinimide (NIS) and phosphorus compounds for syntheses of 2-iodo- and 2-deoxyglycosides

Tomoya Kimura, DAISUKE TAKAHASHI, *Kazunobu Toshima

THE JOURNAL OF ORGANIC CHEMISTRY (American Chemical Society)  80 ( 19 ) 9552 - 9562 2015.09

Research paper (scientific journal), Joint Work, Accepted,  ISSN  0022-3263

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Systematic synthesis of low-molecular weight fucoidan derivatives and their effect on cancer cells

Akihiro Kasai, Shinsuke Arafuka, Nozomi Koshiba, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  13 ( 42 ) 10556 - 10568 2015.08

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1477-0520

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One-pot transformation of N-succinyl chitosan to nitrogen-containing alkyl glycosides using an ionic liquid containing a protic acid

Manabu Aoyagi, Tomoya Kimura, Akio Ohba, Yasushi Katayama, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY LETTERS (The Chemical Society of Japan)  44 ( 11 ) 1467 - 1469 2015.08

Research paper (scientific journal), Joint Work, Accepted,  ISSN  0366-7022

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Regioselective and 1,2-cis-α-stereoselective glycosylation utilizing glycosyl-acceptor-derived boronic ester catalyst

Akira Nakagawa, Masamichi Tanaka, Shun Hanamura, *DAISUKE TAKAHASHI, *Kazunobu Toshima

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  54 ( 37 ) 10935 - 10939 2015.07

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1433-7851

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Hierarchical CaCO₃ chromatography: a stationary phase based on biominerals

Kosuke Sato, *Yuya Oaki, DAISUKE TAKAHASHI, Kazunobu Toshima, *Hiroaki Imai

CHEMISTRY-A EUROPEAN JOURNAL (Wiley‐VCH)  21 ( 13 ) 5034 - 5040 2015.02

Research paper (scientific journal), Joint Work, Accepted

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A solid-phase affinity labeling method for target-selective isolation and modification of proteins

Daichi Kuwahara, Takahiro Hasumi, Hajime Kaneko, Madoka Unno, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  50 ( 98 ) 15601 - 15604 2014.10

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1359-7345

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Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Hiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  12 ( 44 ) 8832 - 8835 2014.09

Research paper (scientific journal), Joint Work, Accepted,  ISSN  1477-0520

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Photo-Induced Glycosylation Using Reusable Organophotoacids

Ryosuke Iwata, Kanjiro Uda, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  50 ( 73 ) 10695 - 10698 2014.07

Research paper (scientific journal), Joint Work, Accepted

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Photodegradation of Amyloid β and Reduction of Its Cytotoxicity to PC12 Cells Using Porphyrin Derivatives

Ayumi Hirabayashi, Yutaka Shindo, Kotaro Oka, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  50 ( 67 ) 9543 - 9546 2014.07

Research paper (scientific journal), Joint Work, Accepted

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Systematic Synthesis of Sulfated Oligofucosides and Their Effect on Breast Cancer MCF-7 Cells

Shinsuke Arafuka, Nozomi Koshiba, *DAISUKE TAKAHASHI,* Kazunobu Toshima*

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  50 ( 69 ) 9831 - 9834 2014.06

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

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Total synthesis of vineomycin B2

Shunichi Kusumi, Satoshi Tomono, Shunsuke Okuzawa, Erika Kaneko, Takashi Ueda, Kaname Sasaki, DAISUKE TAKAHASHI, *Kazunobu Toshima

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (American Chemical Society)  135 ( 42 ) 15909 - 15912 2013.09

Research paper (scientific journal), Joint Work, Accepted

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Chiral Bronsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality

Tomoya Kimura, Maiko Sekine, DAISUKE TAKAHASHI, *Kazunobu Toshima

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  52 ( 46 ) 12131 - 12134 2013.09

Research paper (scientific journal), Joint Work, Accepted,  ISSN  1433-7851

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Design, synthesis and evaluation of a boronic acid based artificial receptor for L-DOPA in aqueous media

Haruna Ueno, Takayuki Iwata, Nozomi Koshiba, *DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  49 ( 88 ) 10403 - 10405 2013.09

Research paper (scientific journal), Joint Work, Corresponding author, Accepted,  ISSN  1359-7345

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The direct and one-pot transformation of xylan into the biodegradable surfactants, alkyl xylosides, is aided by an ionic liquid

Maiko Sekine, Tomoya Kimura, Yasushi Katayama, DAISUKE TAKAHASHI, *Kazunobu Toshima

RSC ADVANCES (Royal Society of Chemistry)  3 ( 43 ) 19756 - 19759 2013.08

Research paper (scientific journal), Joint Work, Accepted,  ISSN  2046-2069

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Light-induced O-Glycosylation of Unprotected Deoxythioglycosyl Donors

Mayuka Nakanishi, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  11 ( 31 ) 5079 - 5082 2013.06

Research paper (scientific journal), Joint Work, Accepted

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Target-selective Photo-degradation of Verotoxin-1 and Reduction of Its Cytotoxicity to Vero Cells Using Porphyrin-globotriose Hybrids

Atsushi Okochi, Shuho Tanimoto, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  49 ( 54 ) 6027 - 6029 2013.05

Research paper (scientific journal), Joint Work, Accepted

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Improved total synthesis of incednam

Akira Takada, Kanjiro Uda, Takashi Ohtani, Shinya Tsukamoto, DAISUKE TAKAHASHI, *Kazunobu Toshima

THE JOURNAL OF ANTIBIOTICS 66 ( 3 ) 155 - 159 2013.02

Research paper (scientific journal), Joint Work, Accepted

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Photodegradation and Inhibition of Drug-Resistant Influenza Virus Neuraminidase Using Anthraquinone-Sialic Acid Hybrids

Yusuke Aoki, Shuho Tanimoto, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  49 ( 12 ) 1169 - 1171 2012.12

Research paper (scientific journal), Joint Work, Accepted

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Carbohydrate recognition and photodegradation by an anthracene-Kemp's acid hybrid

Miyuki Nishibu, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  10 ( 42 ) 8393 - 8395 2012.09

Research paper (scientific journal), Joint Work, Accepted

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Photodegradation of lipopolysaccharides and the inhibition of macrophage activation by anthraquinone-boronic acid hybrids

DAISUKE TAKAHASHI, Takuya Miura, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  48 ( 61 ) 7595 - 7597 2012.06

Research paper (scientific journal), Joint Work, Lead author, Accepted

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Target-Selective Photodegradation of HIV-1 Protease and Inhibition of HIV-1 Replication in Living Cells by Designed Fullerene–sugar Hybrids

Shuho Tanimoto, Satoshi Sakai, Eriko Kudo, Seiji Okada, Shuichi Matsumura, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY AN ASIAN JOURNAL (Wiley‐VCH)  7 ( 5 ) 911 - 914 2012.02

Research paper (scientific journal), Joint Work, Accepted

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Involvement of DNA binding domain in the cellular stability and importin affinity of NF-κB component RelB

Masatoshi Takeiri, Kana Horie, DAISUKE TAKAHASHI, Mariko Watanabe, Ryoichi Horie, Siro Simizu, *Kazuo Umezawa

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  10 ( 15 ) 3053 - 3059 2012.02

Research paper (scientific journal), Joint Work, Accepted

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Efficient and Stereoselective Synthesis of the Disaccharide Fragment of Incednine

Takashi Ohtani, Shohei Sakai, Akira Takada, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC LETTERS (American Chemical Society)  13 ( 22 ) 6126 - 6129 2011.10

Research paper (scientific journal), Joint Work, Accepted

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Degradation of Target Oligosaccharides by Anthraquinone-lectin Hybrids with Light Switching

Yukari Imai, Shingo Hirono, Haruka Matsuba, Yuka Kobayashi, Hirokazu Kawagishi, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY AN ASIAN JOURNAL (Wiley‐VCH)  7 ( 1 ) 97 - 104 2011.10

Research paper (scientific journal), Joint Work, Accepted

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Target-selective Photodegradation of Oligosaccharides by a Fullerene-boronic Acid Hybrid upon Visible Light Irradiation

DAISUKE TAKAHASHI, Shingo Hirono, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  47 ( 42 ) 11712 - 11714 2011.09

Research paper (scientific journal), Joint Work, Lead author, Accepted

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Inhibition of Amyloid β Aggregation and Cytotoxicity by Photodegradation Using a Designed Fullerene Derivative

Yasunori Ishida, Tomohiko Fujii, Kotaro Oka, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMISTRY AN ASIAN JOURNAL (Wiley‐VCH)  6 ( 9 ) 2312 - 2315 2011.09

Research paper (scientific journal), Joint Work, Accepted

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Molecular Design, Chemical Synthesis, and Biological Evaluation of Agents that Selectively Photo-degrade the Transcription Factor Estrogen Receptor-α

Kana Tsumura, Akane Suzuki, Takeo Tsuzuki, Shuho Tanimoto, Hajime Kaneko, Shuichi Matsumura, Masaya Imoto, Kazuo Umezawa, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  9 ( 18 ) 6357 - 6366 2011.06

Research paper (scientific journal), Joint Work, Accepted

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Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Satoshi Tomono, Shunichi Kusumi, DAISUKE TAKAHASHI, *Kazunobu Toshima

TETRAHEDRON LETTERS (Elsevier)  52 ( 18 ) 2399 - 2403 2011.03

Research paper (scientific journal), Joint Work, Accepted

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Photodegradation of Target Oligosaccharides by Light-Activated Small Molecules

DAISUKE TAKAHASHI, Shingo Hirono, Chigusa Hayashi, Masayuki Igarashi, Yoshio Nishimura, *Kazunobu Toshima

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  49 ( 52 ) 10096 - 10100 2010.11

Research paper (scientific journal), Joint Work, Lead author, Accepted

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Total Synthesis of Incednam, the Aglycon of Incednine

Takashi Ohtani, Shinya Tsukamoto, Hiroshi Kanda, Kensuke Misawa, Yoshifumi Urakawa, Takahiro Fujimaki, Masaya Imoto, Yoshikazu Takahashi, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC LETTERS (American Chemical Society)  12 ( 21 ) 5068 - 5071 2010.11

Research paper (scientific journal), Joint Work, Accepted

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A Novel Glycosylation of Inactive Glycosyl Donors Using an Ionic Liquid Containing a Protic Acid under Reduced Pressure Conditions

Yasutaka Kuroiwa, Maiko Sekine, Satoshi Tomono, DAISUKE TAKAHASHI, *Kazunobu Toshima

TETRAHEDRON LETTERS (Elsevier)  51 ( 48 ) 6294 - 6297 2010.09

Research paper (scientific journal), Joint Work, Accepted

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従来の糖供与体よりも安定かつ調整容易なメチルグリコシドや1-OH糖が、再利用可能なプロトン酸含有イオン液体中、速やかに活性化されること、さらに、減圧条件下に付すことで、グリコシル化反応が効率的に進行することを示した論文。

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Photo-degradation of Amyloid β by a Designed Fullerene-sugar Hybrid

Yasunori Ishida, Shuho Tanimoto, DAISUKE TAKAHASHI, *Kazunobu Toshima

MED. CHEM. COMMUN. (Royal Society of Chemistry)  1 ( 3 ) 212 - 215 2010.08

Research paper (scientific journal), Joint Work, Accepted

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新規にデザイン・合成したフラーレンと糖とのハイブリッド分子が、アミロイドβの凝集を阻害するだけでなく、人体に害のない長波長紫外光の照射下、アミドロイドβのモノマーおよびオリゴマーを効果的に光分解することを示した論文。

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Effective and Chemoselective Glycosylations Using 2,3-Unsaturated Sugars

Shunichi Kusumi, Kaname Sasaki, Sainan Wang, Tatsuya Watanabe, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  8 ( 14 ) 3164 - 3178 2010.05

Research paper (scientific journal), Joint Work, Accepted

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生体内におけるリゾチームの糖鎖加水分解反応に着眼し、デザイン・合成した2,3-不飽和糖が2,3-飽和糖および2,3-不飽和-4-ケト糖よりも有意に高い反応性を有することを示し、この反応性の差を利用した化学選択的グリコシル化反応が2,3-ジデオキシ糖鎖の効率的な合成法として有効であることを示した論文。

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Chemoselective Glycosylations Using 2,3-Unsaturated-4-Keto Glycosyl Donors

Shunichi Kusumi, Sainan Wang, Tatsuya Watanabe, Kaname Sasaki, DAISUKE TAKAHASHI, *Kazunobu Toshima

ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry)  8 ( 5 ) 988 - 990 2010.01

Research paper (scientific journal), Joint Work, Accepted

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デザイン合成した2,3-不飽和-4-ケト糖が対応する2,3-不飽和糖および2,3-飽和糖よりも反応性が低下することを示し、この反応性の差を利用した化学選択的グリコシル化反応が2,3-ジデオキシ糖鎖の効率的な合成法として有効であることを示した論文。

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Hydrolysis of Disaccharides by Metal Species in Neutral Homogeneous Conditions

DAISUKE TAKAHASHI, Sakiko Kobayashi, Kana Tsumura, *Kazunobu Toshima

CHEMISTRY LETTERS (The Chemical Society of Japan)  38 ( 7 ) 728 - 729 2009.06

Research paper (scientific journal), Joint Work, Lead author, Accepted

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糖鎖が中性条件下、金属触媒により、効果的に加水分解されることを初めて示した論文。

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The Synthesis of Carbohydrate Microarrays by S-Alkylation of the Glass-supported 2-Bromoacetamides

DAISUKE TAKAHASHI, Hiroshi Tanaka, Emiko Nakane, *Takashi Takahashi

CHEMISTRY LETTERS (The Chemical Society of Japan)  37 ( 12 ) 1252 - 1253 2008.11

Research paper (scientific journal), Joint Work, Lead author, Accepted

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チオアルキル化反応を利用する糖鎖マイクロアレイの合成と、合成したマイクロアレイ上にて糖鎖－タンパク間相互作用が高感度で観測されることを示した論文。

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Target-selective Photo-degradation of HIV-1 Protease by a Fullerene-sugar Hybrid

Shuho Tanimoto, Satoshi Sakai, Shuichi Matsumura, DAISUKE TAKAHASHI, *Kazunobu Toshima

CHEMICAL COMMUNICATIONS (Royal Society of Chemistry)  0 ( 44 ) 5767 - 5769 2008.10

Research paper (scientific journal), Joint Work, Accepted

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フラーレンがタンパクを光分解することを示し、フラーレンと糖とのハイブリッド分子が、エイズ関連タンパクであるHIV-1プロテアーゼを選択的に光分解することを示した論文。

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鎖状鍵中間体を利用するデオキシオリゴ糖の合成と糖鎖マイクロアレイの開発研究

*高橋 大介

博士学位論文 (東京工業大学大学院理工学研究科)   2006.03

Doctoral thesis, Single Work, Lead author, Last author, Corresponding author

Stereoselective Synthesis of Oligo-α(2,8)-3-deoxy-D-manno-2-octulosonic Acid Derivatives.

Hiroshi Tanaka, DAISUKE TAKAHASHI, *Takashi Takahashi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  45 ( 5 ) 770 - 773 2005.12

Research paper (scientific journal), Joint Work, Accepted

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KDOの立体選択的グリコシル化反応の開発と、本反応を基盤とするオリゴ-α(2,8)-KDOの立体選択的合成に関する論文。

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Efficient Stereoselective Synthesis of γ-N-Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups

Hiroshi Tanaka, Yuki Iwata, DAISUKE TAKAHASHI, Masaatu Adachi, *Takashi Takahashi

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (American Chemical Society)  127 ( 6 ) 1630 - 1631 2005.01

Research paper (scientific journal), Joint Work, Accepted,  ISSN  0002-7863

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一級アミドを糖受容体とするグリコシル化反応が、高収率・高立体選択的に進行することを示し、様々なＮ結合型糖アミノ酸が効率的に合成されることを示した論文。

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Synthesis of 2,3,6-Trideoxy-Containing Disaccharides by Cyclization and Glycosidation through the Sequential Activation of Sulfoxide and Methylsulfanyl Groups in a One-Pot Procedure

Toru Amaya, DAISUKE TAKAHASHI, Hiroshi Tanaka, *Takashi Takahashi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (Wiley‐VCH)  42 ( 16 ) 1833 - 1836 2003.04

Research paper (scientific journal), Joint Work, Accepted

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新規にデザイン及び合成した鎖状中間体を利用する連続的環化-グリコシル化反応がワンポットで進行することを示し、様々な2,3,6-トリデオキシ糖含有糖鎖が簡便に合成されることを示した論文。

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