論文 - 戸嶋　一敦

2-Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein-Photodegrading Agent and Its Application as a H<inf>2</inf>O<inf>2</inf>-Activatable Photosensitizer

Takashi Kitamura, Saori Shiroshita, *Daisuke Takagashi, *Kazunobu Toshima

Chemistry - A European Journal （Wiley-VCH ）  26 （ 63 ） 14351 - 14358 2020年11月

研究論文（学術雑誌）, 共著, 査読有り,  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年08月

研究論文（学術雑誌）, 共著, 査読有り,  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

Tanaka M., Sato K., Yoshida R., Nishi N., Oyamada R., Inaba K., *Takahashi D., *Toshima K.

Nature Communications （Springer Nature）  11 （ 1 ） 2431 2020年05月

研究論文（学術雑誌）, 共著, 査読有り

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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.

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

Iibuchi N., Eto T., Aoyagi M., Kurinami R., Sakai H., Hasobe T., *Takahashi D., * Toshima K

Organic and Biomolecular Chemistry （The Royal Society of Chemistry）  18 （ 5 ） 851 - 855 2020年01月

研究論文（学術雑誌）, 共著, 査読有り,  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 84 （ 22 ） 14724 - 14732 2019年10月

研究論文（学術雑誌）, 共著, 査読有り

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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年03月

研究論文（学術雑誌）, 共著, 査読有り,  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年10月

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年08月

研究論文（学術雑誌）, 査読有り,  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年06月

研究論文（学術雑誌）, 査読有り,  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年03月

研究論文（学術雑誌）, 共著, 査読有り,  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年02月

研究論文（学術雑誌）, 共著, 査読有り,  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年10月

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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年09月

研究論文（学術雑誌）, 共著, 査読有り

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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年03月

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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年12月

研究論文（学術雑誌）, 共著, 査読有り

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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年10月

研究論文（学術雑誌）, 共著, 査読有り

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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年07月

研究論文（学術雑誌）, 共著, 査読有り

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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年05月

研究論文（学術雑誌）, 共著, 査読有り

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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年05月

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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年05月

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