Papers - Toshima, Kazunobu

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

Nishi N., Sueoka K., Iijima K., Sawa R., Takahashi D., Toshima K.

Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  57 ( 42 ) 13858 - 13862 2018.10

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.

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

Shota Sotokawa, Takashi Kitamura, Daisuke Takahashi, *Kazunobu Toshima

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

Research paper (scientific journal), Accepted,  ISSN  13597345

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© 2018 The Royal Society of Chemistry. A purpose-designed anthraquinone-horseradish peroxidase (HRP)-cell penetrating peptide hybrid 1 showed high and effective cell permeability. Furthermore, 1 exhibited enzymatic activity without photo-irradiation, whereas significant self-degradation and loss of enzymatic activity occurred upon photo-irradiation in living cells.

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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), 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, Accepted,  ISSN  0022-3263

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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, Accepted,  ISSN  1520-5126

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

R. Takagi, A. Takeda, D. Takahashi, K. Toshima

Chemistry-An Asian Journal 12 ( 20 ) 2656 - 2659 2017.10

Research paper (scientific journal), Joint Work, Accepted

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Electrochemical Preparation of Platinum Nanoparticles from Bis(acetylacetonato)platinum(II) in Some Aprotic Amide-type Ionic Liquids

S. Sultana, N. Tachikawa, K. Yoshii, K. Toshima, L. Magagnin, Y. Katayama

Electrochimica Acta 249   263 - 270 2017.09

Research paper (scientific journal), Joint Work, Accepted

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Regio- and Stereoselective β-Mannosylation Using a Boronic Acid Catalyst and Its Application to the Synthesis of a Tetrasaccharide Repeating Unit of Lipopolysaccharide Derived from E. Coli O75

N. Nishi, J. Nashida, E. Kaji, D. Takahashi, K. Toshima

Chemical Communications 53   3018 - 3020 2017.03

Research paper (scientific journal), Joint Work, Accepted

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Total Synthesis of Aquayamycin

Kusumi, Shunichi; Nakayama, Harunobu; Kobayashi, Takumi; Kuriki Hajime, Matsumoto Yuka, Takahashi Daisuke, Toshima Kazunobu

Chemistry-A European Journal 22 ( 52 ) 18733 - 18736 2016.12

Research paper (scientific journal), Joint Work, Accepted

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

Tanaka Masamichi, Takahashi Daisuke, Toshima Kazunobu

Organic Letters 18 ( 19 ) 5030 - 5033 2016.10

Research paper (scientific journal), Joint Work, Accepted

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Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid

Kimura Tomoya, Eto Takahiro, Takahashi Daisuke, Toshima Kazunobu

Organic Letters 18 ( 13 ) 3190 - 3193 2016.07

Research paper (scientific journal), Joint Work, Accepted

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Electrochemical Behavior of Bis(acetylacetonato)platinum(II) Complex in an Amide-Type Ionic Liquid

Sultana Sharmin, Tachikawa Naoki, Yoshii Kazuki, Magagnin Luca, Toshima Kazunobu, Katayama Yasushi

Journal of The Electrochemical Society 163 ( 8 ) D401 - D406 2016.05

Research paper (scientific journal), Joint Work, Accepted

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Glycosyl-Acceptor-Derived Boronic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor

Tanaka Masamichi, Nashida Junki, Takahashi Daisuke, Toshima Kazunobu

Organic Letters 18 ( 9 ) 2288-2291 2016.05

Research paper (scientific journal), Joint Work, Accepted

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

Takahashi Daisuke,Nagao Takashi,Sotokawa Shota, Toshima Kazunobu

MedChemComm 7 ( 6 ) 1224-1228 2016.05

Research paper (scientific journal), Joint Work, 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

Okuyama Mai, Ueno Haruna, Kobayashi Yuka, Kawagishi Hirokazu, Takahashi Daisuke, Toshima Kazunobu

Chemical Communications 52 ( 10 ) 2169 - 2172 2016.02

Research paper (scientific journal), Joint Work, Accepted

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

Kasai Akihiro, Arafuka Shinsuke, Koshiba Nozomi, Takahashi Daisuke, Toshima Kazunobu

Organic & Biomolecular Chemistry 13 ( 42 ) 10556 - 10568 2015.11

Research paper (scientific journal), Joint Work, Accepted

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Electrochemical preparation of palladium nanoparticles in bis(trifluoromethylsulfonyl)amide ionic liquids consisting of pyrrolidinium cations with different alkyl chain lengths

Katayama Yasushi,Oshino Yosuke,Ichihashi Naoaki,Naoki Tachikawa, Yoshii Kazuki,Toshima Kazunobu

Electrochimica Acta 183   37 - 41 2015.11

Research paper (scientific journal), Joint Work, Accepted

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

Aoyagi Manabu, Kimura Tomoya, Ohba Akio, Katayama Yasushi, Takahashi Daisuke, Toshima Kazunobu

Chemistry Letters 44   1467 - 1469 2015.11

Research paper (scientific journal), Joint Work, Accepted

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

Kimura Tomoya, Takahashi Daisuke, Toshima Kazunobu

Journal of Organic Chemistry 80 ( 19 ) 9552 - 9562 2015.10

Research paper (scientific journal), Joint Work, Accepted

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