Details of a Researcher - Takahashi, Daisuke

Papers - Takahashi, Daisuke

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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

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

© 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

© 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

© 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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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

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

© 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

© 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

© 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

© 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

© 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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