東京大学大学院薬学系研究科 薬化学教室

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論文紹介

代表的論文

非平面アミドの化学 Non-planar Amides Chemistry

  • Robust Trans-Amide Helical Structure of Oligomers of Bicyclic Mimics of β-Proline: Impact of Positional Switching of Bridgehead Substituent on Amide Cis-Trans Equilibrium.
    Siyuan Wang; Yuko Otani; Xin Liu; Masatoshi Kawahata; Kentaro Yamaguchi; Tomohiko Ohwada
    Journal of Organic Chemistry, 2014, 79 (11), pp 5287-5300.
    Abstract
  • Secondary Structure of Homo-thiopeptides Based on a Bridged β-Proline Analogue: Preferred Formation of Extended Strand Structures with Trans-Thioamide Bonds
    Yuko Otani, Tetsuharu Hori, Masatoshi Kawahata, Kentaro Yamaguchi and Tomohiko Ohwada
    Tetrahedron, 2012,68 (23), 4418-4428
    Special Issue (Symposium in print) on Chemistry of Foldamers
    Abstract
  • Water-stable Helical Structure of Tertiary Amides of Bicyclic β-Amino Acid Bearing 7-Azabicyclo[2.2.1]heptane. Full Control of Amide Cis-Trans Equilibrium by Bridgehead Substitution.
    Masahiro Hosoya; Yuko Otani; Masatoshi Kawahata; Kentaro Yamaguchi; Tomohiko Ohwada
    Journal of the American Chemical Society, 2010, 132, 42, 14780-14789.
    Abstract
  • Nonplanar Structures of Thioamides Derived from 7-Azabicyclo[2.2.1]heptane. Electronically Tunable Planarity of Thioamides
    Hori, T.; Otani, Y.; Kawahata, M.; Yamaguchi, K.; Ohwada, T.
    Journal of Organic Chemistry, 2008, 73, 9102-9108.
    Abstract
  • Oligomers of beta-Amino Acid Bearing Nonplanar Amides form Ordered Structures
    Yuko Otani, Shiroh Futaki, Tatsuto Kiwada, Yukio Sugiura, Atsuya Muranaka, Nagao Kobayashi, Masanobu Uchiyama, Kentrao Yamaguchi and Tomohiko Ohwada
    Tetrahedron, 2006, 62. 11635-11644.
    Abstract
  • alpha,alpha-Disubstituted Amino Acids Bearing a Large Hydrocarbon Ring. Peptide Self-Assembly through Novel Hydrophobic Recognition
    Ohwada, T.; Kojima, D.; Kiwada, T.; Futaki, S.; Sugiura, Y.; Yamaguchi, K.; Nishi, Y.; Kobayashi, Y.
    Chemistry-A European Journal, 2004, 10, 617-626.
    Abstract
  • An Evaluation of Amide Group Planarity in 7-Azabicyclo[2.2.1]heptane Amides. Low Amide Bond Rotation Barrier in Solution.
    Yuko Otani; Osamu Nagae; Yuji Naruse; Satoshi Inagaki; Masashi Ohno; Kentaro Yamaguchi; Gaku Yamamoto; Masanobu Uchiyama; Tomohiko Ohwada
    Journal of the American Chemical Society, 2003, 125, 15191-15199.
    Abstract

非平面ニトロソアミンの化学 S−ニトロシル化とNO発生と生物機能調整
Non-planar N-Nitrosamine Chemistry and Biological Relevance

  • Trans-nitrosylation directs TRPA1 selectivity in N-nitrosamine activators.
    Daisuke Kozai, Yoji Kabasawa, Maximilian Ebert, Shigeki Kiyonaka, Firman, Yuko Otani, Tomohiro Numata, Nobuaki Takahashi, Yasuo Mori, Tomohiko Ohwada
    Molecular Pharmacology, 2014, 85, 175-185.
    Abstract
  • Attenuated Desensitization of β-Adrenergic Receptor by Water-Soluble N-Nitrosamines That Induce S-Nitrosylation Without NO Release
    Noriko Makita, Yoji Kabasawa, Yuko Otani, Firman, Junichiro Sato, Makiko Hashimoto, Michio Nakaya, Hiroaki Nishihara, Masaomi Nangaku, Hitoshi Kurose, Tomohiko Ohwada and Taroh Iiri
    Circulation Research, 2013, 112, 327-334.
    Abstract
  • Visible-light-triggered Release of Nitric Oxide from N-Pyramidal Nitrosamines
    Fumika Karaki, Yoji Kabasawa, Takahiro Yanagimoto, Nobuhiro Umeda, Firman, Yasuteru Urano, Tetsuo Nagano, Yuko Otani, and Tomohiko Ohwada
    Chemistry - A European Journal, 2012, 18 (4), 1127-1141.
    Abstract
  • 7-Azabicyclo[2.2.1]heptane as a Structural Motif to Block Mutagenicity of Nitrosamines
    Tomohiko Ohwada, Satoko Ishikawa, Yusuke Mine, Keiko Inami, Takahiro Yanagimoto, Fumika Karaki, Yoji Kabasawa, Yuko Otani, Masataka Mochizuki
    Bioorganic & Medicinal Chemistry, 2011, 19, 2726-2741.
    Abstract
  • Transnitrosation of Thiols from Aliphatic N-Nitrosamines: S-Nitrosation and Indirect Generation of Nitric Oxide
    Yanagimoto, T.; Toyoda, T.; Matsuki, N.; Makino, Y.; Uchiyama, S.; Ohwada, T.
    Journal of the American Chemical Society, 2007, 129, 736-737.
    Abstract
  • Structural Features of Aliphatic N-Nitrosamines of 7-Azabicyclo[2.2.1]heptanes That Facilitate N-NO Bond Cleavage
    Tomohiko Ohwada,Motoko Miura, Haruko Tanaka, Shigeru Sakamoto, Kentaro Yamaguchi, Hirotaka Ikeda, and Satoshi Inagaki
    Journal of the American Chemical Society, 2001, 123, 10164-10172.
    Abstract

芳香族官能基化反応の開発 超求電子体の化学Aromatic Functionalized
Reactions Involving Dicationic and Monocationic Superelectrophiles

  • Acid-promoted Chemoselective Introduction of Amide Functionality onto Aromatic Compounds Mediated by Isocyanate Cation Generated from Carbamate.
    Akinari Sumita, Hiroaki Kurouchi, Yuko Otani, Tomohiko Ohwada
    Chemistry - An Asian Journal, 2014, 9 (10), 2995–3004.
    Abstract
  • Protonation Switching to Least Basic Heteroatom of Carbamate through Cationic Hydrogen Bonding Promotes Formation of Isocyanate Cation
    Hiroaki Kurouchi, Akinari Sumita, Yuko Otani, Tomohiko Ohwada
    Chemistry - A European Journal, 2014, 20, 8682-8690.
    Abstract
  • Cyclization of Arylacetoacetates to Indene and Dihydronaphthalene Derivatives in Strong Acid. Evidenece for Involvement of Further Protonation of O,O-Diprotonated beta-Ketoester, Leading to Enhancement of Cyclization
    Hiroaki Kurouchi, Hiromichi Sugimoto, Yuko Otani, Tomohiko Ohwada
    Journal of the American Chemical Society, 2010, 132, 807-815.
    Abstract
  • Superacid-catalyzed Intramolecular Cyclization Reaction of Arylcyanopropionate: Geminal Substitution Effect on Superelectrophilicity
    Nakamura, S.; Sugimoto, H.; Ohwada, T.
    Journal of Organic Chemistry, 2008, 73(11), 4219-4224.
    Abstract
  • Formation of 4H-1,2-Benzoxazines by Intramolecular Cyclization of Nitroalkanes. Scope of Aromatic Oxygen-functionalization Reaction Involving a Nitro Oxygen Atom, and Mechanistic Insights
    Nakamura, S.; Sugimoto, H.; Ohwada, T.
    Journal of the American Chemical Society, 2007, 129, 1724-1732.
    Abstract
  • Generation and Application of o-Benzoquinone Methides Bearing Various Substituents on the Benzene Ring.
    Sugimoto, H.; Nakamura, S.; Ohwada, T.
    Advanced Synthsis & Catalysis, 2007, 349, 669-679.
    Abstract
  • The Prototype Pictet-Spengler Reactions Catalyzed by Superacids. Involvement of Dicationic Superelectrophiles
    Yokoyama,A.; Ohwada, T.; Shudo, K.
    Journal of Organic Chemistry, 1999, 64, 611-617.
    Abstract
  • Superacid-catalyzed Electrocyclization of Diphenylmethyl Cations to Fluorenes. Kinetic and Theoretical Revisit Supporting the Involvement of Ethylene Dications
    Ohwada, T;Suzuki, T.; Shudo, K.
    Journal of the American Chemical Society, 1998, 120, 4629-4637.
    Abstract

膜タンパク質の機能を調整する有機分子のデザインと合成Design and Synthesis of
Membrane Protein Function Modulators. Mechanistic Interests.

  • Discovery of a Tamoxifen-related compound that suppresses glial L-glutamate transport activity without interaction with estrogen receptors"
    Kaoru Sato , Jun-ichi Kuriwaki, Kanako Takahashi, Yoshihiko Saito, Jun-ichiro Oka, Yuko Otani, Yu Sha, Ken Nakazawa, Yuko Sekino, Tomohiko Ohwada
    ACS Chemical Neuroscience, 2012, 3, 105-113.
    Abstract
  • Molecular mechanism of pharmacological activation of BK channels
    Guido Gessner, Yong-Mei Cui, Yuko Otani, Tomohiko Ohwada, Malle Soom, Toshinori Hoshi, and Stefan H. Heinemann
    Proceedings of the National Academy of Sciences of the U. S. A. 2012, 109 (9) 3552-3557.
    Abstrct
  • Synthesis and Evaluation of Lysophosphatidylserine Analogs as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidyl- threonine and Its 2-Deoxy Derivative
    Masazumi Iwashita, Kumiko Makide, Taro Nonomura, Yoshimasa Misumi, Yuko Otani, Mayuko Ishida, Ryo Taguchi, Masafumi Tsujimoto, Junken Aoki, Hiroyuki Arai, Tomohiko Ohwada
    Journal of Medicinal Chemistry, 2009, 52 (19), 5837-5863.
    Abstract
  • Design, Synthesis and Characterization of BK Channel Openers Based on Oximation of Abietane Diterpene Derivatives
    Yong-Mei Cui, Eriko Yasutomi, Yuko Otani, Katsutoshi Ido, Takashi Yoshinaga, Kohei Sawada, and Tomohiko Ohwada
    Bioorganic & Medicinal Chemistry, 2010, 18, 8642-8659.
    Abstract
  • Novel Oxime and Oxime Ether Derivatives of 12,14-Dichlorodehydroabietic Acid: Design, Synthesis and BK Channel-Opening Activity
    Cui, Y.-M.; Yasutomi, E.; Otani, Y.; Yoshinaga, T.; Ido, K.; Sawada, K. Kawahata, M. ; Yamaguchi, K.; Ohwada, T.
    Bioorganic & Medicinal Chemistry Letters, 2008, 18 (24), 6386-6389.
    Abstract
  • Dehydroabietic Acid Derivatives as a Novel Scaffold for Large-Conductance Calcium-Activated K+ Channel Openers.
    Ohwada, T.; Nonomura, T.; Maki, K.; Sakamoto, K.; Ohya, S.; Muraki, K; Imaizum、Y.
    Bioorganic & Medicinal Chemistry Letters, 2003, 13, 3971-3974.
    Abstract

理論計算による有機化学Computational Studies

  • Enantiodivergent Deprotonation-Acylation of α-Amino Nitriles
    Michiko Sasaki, Tomo Takegawa, Kunihiro Sakamoto, Yuri Kotomori, Yuko Otani, Tomohiko Ohwada, Masatoshi Kawahata, Kentaro Yamaguchi, and Kei Takeda
    Angewandte Chemie International Edtion, 2013, 52 (49), 12956-12960.
    Abstract
  • Theoretical study on the excited states of heteroarene chromophores: Comparison of calculated and experimental values
    Tsuji, T.; Onoda, M.; Otani, Y.; Ohwada, T.; Nakajima, T.; Hirao, K.
    Chemical Physics Letters, 2009, 473 (1-3), 29, 196-200
    Abstract
  • Theoretical Revisit of Regioselectivities of Diels-Alder Reactions. Quantitative Evaluation of Multicentered Reactivity Based on Reactive Hybrid Orbitals
    Hirao, H. ; Ohwada, T.
    Journal of Physical Chemistry A. 2005, 109, 816-824.
    Abstract
  • Rationale for the Acidity of Meldrum's Acid. Consistent Relation of C-H Acidities to the Properties of Localized Reactive Orbital
    Nakamura, S.; Hirao, H.; Ohwada, T.
    Journal of Organic Chemistry, 2004, 69, 4309-4316.
    Abstract

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