物質と生命を光でつなぐ分子技術の開発

• Project/Area Number: 17H06173
• Research Category: Grant-in-Aid for Scientific Research (S)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: The University of Tokyo
• Principal Investigator: 内山 真伸 東京大学, 大学院薬学系研究科(薬学部), 教授 (00271916)
• Co-Investigator(Kenkyū-buntansha): 澤田 大介 岡山大学, 医歯薬学総合研究科, 教授 (00338691) ; 村中 厚哉 国立研究開発法人理化学研究所, 開拓研究本部, 専任研究員 (20374902) ; 神野 伸一郎 愛知学院大学, 薬学部, 教授 (20537237)
• Project Period (FY): 2017-05-31 – 2022-03-31
• Project Status: Granted (Fiscal Year 2020)
• Budget Amount: ¥212,290,000 (Direct Cost: ¥163,300,000、Indirect Cost: ¥48,990,000); Fiscal Year 2020: ¥25,090,000 (Direct Cost: ¥19,300,000、Indirect Cost: ¥5,790,000); Fiscal Year 2019: ¥27,690,000 (Direct Cost: ¥21,300,000、Indirect Cost: ¥6,390,000); Fiscal Year 2018: ¥47,190,000 (Direct Cost: ¥36,300,000、Indirect Cost: ¥10,890,000); Fiscal Year 2017: ¥92,300,000 (Direct Cost: ¥71,000,000、Indirect Cost: ¥21,300,000)
• Keywords: π分子 / 光応答分子 / 光応答性分子 / 近赤 外光分子技術 / 機能性π分子 / 化学系薬学 / 有機化学

Outline of Annual Research Achievements

π共役系有機分子は、光を利活用する物質科学・生命科学において、重要な基本電子構造を有する分子群である。しかし現在でもπ共役系化合物の合成・置換基導入、ならびに機能（吸光発光特性、量子収率、熱安定性など）の制御には大きな制限があり、生命科学・物質科学への展開が阻まれている。本研究では、代表者らがこれまで培ってきた有機合成化学・理論化学・分光学・元素化学を結集し、光を利活用するための新奇π共役系有機化合物の提案と設計・合成法の開発、多様化、ならびに電子と構造・機能の自在制御を目指している。本研究を通じて、物質と生命を光でつなぐ分子技術に挑んでいる。
[π共役系有機分子をつくる]では、「芳香環を繋ぐ 」「不活性結合の活性化」「π結合へのホウ素、ケイ素、炭素導入」「常温常圧での C2 発生とナノカーボン合成 」「電荷シフト結合の活性化」などを開発した。
[π共役系有機分子で光を操る]では、「近赤外有機色素 」「円偏光発光分子」「新たな吸光発光分子」などの開発に成功した。
[π共役系有機分子を応用する・活用する]では、外部環境を認識する分子の開発に取り組み、「極性」「キラリティー」「pH 」 に応答する分子を開発し、「近赤外光に応答する光音響プローブの開発」にも成功した。
複数の論文が SYNFACTS などに掲載されるなど高い学術的評価を得ており、多くの新たな科学へと繋がると期待されている。本研究は、これまで勘や経験に頼ってきた合成化学に、理論計算という「予言性」を組み合わせることで、分子・形・反応・機能を生み出そうとするものであり、独自性の極めて高いものである。こうして確立した「実験と理論を両輪とする研究手法」により、当初全く予想していなかった研究成果にも恵まれている。

Current Status of Research Progress

1: Research has progressed more than it was originally planned.

Reason

各課題において順調に研究が進展しており関連分野も含め多くの重要な知見が得られている。いくつかの研究においては当初全く予想していなかった研究成果にも恵まれいる。
[π共役系有機分子をつくる]プロジェクトにおいて開発した反応は、そのほとんどが当初の目的を超える意外性と有用性を備えた「ものづくり」の道具となることが判明した。これらの新反応を基盤に、光を利活用するための機能性π共役系有機分子創製に繋げていきたい。
[π共役系有機分子で光を操る]プロジェクトで開発した分子は、紫外・可視・近赤外領域の吸収・発光分子として広く光を活用できるツールとなりそうである。また、「極性」 「キラリティー」 「pH」 などの外部環境に応答する吸光発光分子の開発にも成功しており、様々な応用が期待できる。この間に開発した「反応経路探索法」は理論研究としての学術的な価値と同時に、こうした励起状態の分子設計にも有効であることが判明しつつあり、今後の光利活用分子や光物性の解析に応用が期待される。
[π共役系有機分子を応用する・活用する]プロジェクトでは、独自に開発した光利活用分子の性質を利用してバイオイメージングで生体組織の深部まで可視化したり、キラリティーを感知するシステムの構築にも成功している。組織透過性の高い近赤外光を吸収して熱に変える光音響プローブの開発にも成功している。これらの光利活用分子は現在様々な分野での応用研究に期待が持たれており、今後明らかにしていきたい。
以上の研究の過程で、意外な成果も数多く得られている。「天然物の複雑生合成経路の解明」や「光による新たな分子活性化機構の発見」 さらには「心筋細胞を増殖させる分子 」 など予想外の発見が得られている。これらは当初の計画にはなかった全く予想外の研究成果であり、現在新たな医薬品開発への展開、光反応の開発、新分野の開拓を目指し、研究を行っている。

Strategy for Future Research Activity

今後は、治療・診断・光活用材料などの応用を見据えて、各技術の要求する物性と我々の新奇π共役系化合物の接点を見出し、代表者らがこ れまで培ってきた有機合成化学・理論化学・分光学・元素化学を結集し、光と構造、物性の自在制御を目指す。特にこれまでに多くの知見を有 するフタロシアニンやポルフィリン、ローダミン系の色素を中心に理論化学支援によるテーラーメード設計を行い、化合物の安定性を損なわな いように、LUMO準位を下げることによって狭いHOMO-LUMOギャップを持つような分子を設計・合成する。さらに、周辺置換基、中心金属などを 利用して物性(光電変換材料、近赤外蛍光色素など)に適した性質を付与すると同時に、新たな近赤外色素設計に向けて理論的・物理化学的な アプローチを試みる。芳香属性の起源などに着目しながら、経験と勘に頼っていた従来の合成化学的手法に加えて、積極的に量子化学計算を用 いることで、特定の機能を持たせた近赤外色素を合理的に設計する独自の分子設計法を開発する。

Research Products

• [Journal Article] Synthesis of a Black Dye with Absorption Capabilities Across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid (2020)
  • Author(s): Wang Yue、Kai Hiroto、Ishida Masatoshi、Gokulnath Sabapathi、Mori Shigeki、Murayama Tomotaka、Muranaka Atsuya、Uchiyama Masanobu、Yasutake Yuhsuke、Fukatsu Susumu、Notsuka Yusuke、Yamaoka Yoshihisa、Hanafusa Mamiko、Yoshizawa Michito、Kim Gakhyun、Kim Dongho、Furuta Hiroyuki
  • Journal Title: Journal of the American Chemical Society Volume: 142 Pages: 6807-6813
  • DOI: 10.1021/jacs.0c01824
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Preparation, Spectroscopic Characterization and Theoretical Study of a Three-Dimensional Conjugated 70 π-Electron Thiophene 6-mer Radical Cation π-Dimer (2020)
  • Author(s): T. Fujiwara, A. Muranaka, T. Nishinaga, S. Aoyagi, N. Kobayashi, M. Uchiyama, H. Otani, M. Iyoda
  • Journal Title: Journal of the American Chemical Society Volume: 142 Pages: 5933-5937
  • DOI: 10.1021/jacs.9b13573
  • Peer Reviewed
• [Journal Article] Silaboration of [1.1.1]Propellane: Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives (2020)
  • Author(s): Kondo Masaki、Kanazawa Junichiro、Ichikawa Tomohiro、Shimokawa Takumi、Nagashima Yuki、Miyamoto Kazunori、Uchiyama Masanobu
  • Journal Title: Angewandte Chemie International Edition Volume: 59 Pages: 1970-1974
  • DOI: 10.1002/anie.201909655
  • Peer Reviewed
• [Journal Article] Ring‐Opened Hemiporphyrazines: Helical Molecules Exhibiting Circularly Polarized Luminescence (2020)
  • Author(s): Tanaka Yusuke、Murayama Tomotaka、Muranaka Atsuya、Imai Eiyu、Uchiyama Masanobu
  • Journal Title: Chemistry A European Journal Volume: 26 Pages: 1768-1771
  • DOI: 10.1002/chem.201905246
  • Peer Reviewed
• [Journal Article] Lipshutz-type bis(amido)argentates for directed ortho argentation (2020)
  • Author(s): Noriyuki Tezuka, Keiichi Hirano, Andrew J. Peel, Andrew E. H. Wheatley, Kazunori Miyamoto, Masanobu Uchiyama
  • Journal Title: Chemical Science Volume: 11 Pages: 1855-1861
  • DOI: 10.1039/c9sc06060j
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Evolving Fluorophores into Circularly Polarized Luminophores with a Chiral Naphthalene Tetramer: Proposal of Excimer Chirality Rule for Circularly Polarized Luminescence (2019)
  • Author(s): Kazuto Takaishi, Kazuhiro Iwachido, Ryosuke Takehana, Masanobu Uchiyama, Tadashi Ema
  • Journal Title: Journal of the American Chemical Society Volume: 141 Pages: 6185-6190
  • DOI: 10.1021/jacs.9b02582
  • Peer Reviewed
• [Journal Article] Diaryl-λ3-chloranes: Versatile Synthesis and Unique Reactivity as Aryl Cation Equivalent (2019)
  • Author(s): Nakajima Misuzu、Miyamoto Kazunori、Hirano Keiichi、Uchiyama Masanobu
  • Journal Title: Journal of the American Chemical Society Volume: 141 Pages: 6499-6503
  • DOI: 10.1021/jacs.9b02436
  • Peer Reviewed
• [Journal Article] Quadruple Borylation of Terminal Alkynes (2019)
  • Author(s): Daiki Yukimori, Yuki Nagashima, Chao Wang, Atsuya Muranaka, and Masanobu Uchiyama
  • Journal Title: Journal of the American Chemical Society Volume: 141 Pages: 9819-9822
  • DOI: 10.1021/jacs.9b04665
  • Peer Reviewed
• [Journal Article] Synthesis of Belt- and Mobius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization (2019)
  • Author(s): Nishigaki Shuhei、Shibata Yu、Nakajima Atsuya、Okajima Hajime、Masumoto Yui、Osawa Taisei、Muranaka Atsuya、Sugiyama Haruki、Horikawa Ayano、Uekusa Hidehiro、Koshino Hiroyuki、Uchiyama Masanobu、Sakamoto Akira、Tanaka Ken
  • Journal Title: Journal of the American Chemical Society Volume: 141 Pages: 14955-14960
  • DOI: 10.1021/jacs.9b06197
  • Peer Reviewed
• [Journal Article] Design of Photostable, Activatable Near‐Infrared Photoacoustic Probes Using Tautomeric Benziphthalocyanine as a Platform (2019)
  • Author(s): Naoyuki Toriumi, Norihito Asano, Takayuki Ikeno, Atsuya Muranaka, Kenjiro Hanaoka, Yasuteru Urano, Masanobu Uchiyama
  • Journal Title: Angewandte Chemie International Edition Volume: 58 Pages: 7788-7791
  • DOI: 10.1002/anie.201903303
  • Peer Reviewed
• [Journal Article] Non-transition Metal-Mediated Diverse Aryl-Heteroatom Bond Formation of Arylammonium Salts (2019)
  • Author(s): Dong-Yu Wang, Xin Wen, Chaodong Xiong, Jian-Nan Zhao, Chun-Yong Ding, Qian Meng, Hu Zhou, Chao Wang, Masanobu Uchiyama, Xiao-Jie Lu, and Ao Zhang
  • Journal Title: iScience Volume: 15 Pages: 307-315
  • DOI: 10.1016/j.isci.2019.04.038
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Characterization of a Small Molecule That Promotes Cell Cycle Activation of Human Induced Pluripotent Stem Cell-Derived Cardiomyocytes (2019)
  • Author(s): Ito Masamichi、Hara Hironori、Takeda Norifumi、Naito Atsuhiko T.、Nomura Seitaro、Kondo Masaki、Hata Yutaka、Uchiyama Masanobu、Morita Hiroyuki、Komuro Issei
  • Journal Title: J Mol Cell Cardiol. Volume: 128 Pages: 90-95
  • DOI: 10.1016/j.yjmcc.2019.01.020
  • Peer Reviewed / Open Access
• [Journal Article] A Protocol for an Iodine-Metal Exchange Reaction on Cubane Using Lithium Organozincates (2019)
  • Author(s): Yumi Kato, Craig M. Williams, Masanobu Uchiyama, Seijiro Matsubara
  • Journal Title: Organic Letters Volume: 21 Pages: 473-475
  • DOI: 10.1021/acs.orglett.8b03721
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO2 (2019)
  • Author(s): Takaishi Kazuto、Okuyama Takafumi、Kadosaki Shota、Uchiyama Masanobu、Ema Tadashi
  • Journal Title: Organic Letters Volume: 21 Pages: 1397-1401
  • DOI: 10.1021/acs.orglett.9b00117
  • Peer Reviewed
• [Journal Article] Alkynylboration Reaction Leading to Boron-containing π-Extended cis-Stilbenes as a Highly Tunable Fluorophore (2019)
  • Author(s): Nogami Marina、Hirano Keiichi、Morimoto Kensuke、Tanioka Masaru、Miyamoto Kazunori、Muranaka Atsuya、Uchiyama Masanobu
  • Journal Title: Organic Letters Volume: 21 Pages: 3392-3395
  • DOI: 10.1021/acs.orglett.9b01132
  • Peer Reviewed
• [Journal Article] A Direct, Chemo-, and Regioselective Cross-Coupling Reaction of Arenes via Sequential Directed ortho Cuprations and Oxidation (2019)
  • Author(s): Tezuka Noriyuki、Hirano Keiichi、Uchiyama Masanobu
  • Journal Title: Organic Letters Volume: 21 Pages: 9536-9540
  • DOI: 10.1021/acs.orglett.9b03719
  • Peer Reviewed
• [Journal Article] Organic Monolithic Natural Hyperbolic Material (2019)
  • Author(s): Lee Yeon Ui、Gaudin Olivier P. M.、Lee KwangJin、Choi Eunyoung、Placide Virginie、Takaishi Kazuto、Muto Tsuyoshi、Andre Pascal、Muranaka Atsuya、Uchiyama Masanobu、Mathevet Fabrice、Aoyama Tetsuya、Wu JeongWeon、D’Aleo Anthony、Ribierre Jean-Charles
  • Journal Title: ACS Photonics Volume: 6 Pages: 1681-1689
  • DOI: 10.1021/acsphotonics.9b00185
  • Peer Reviewed
• [Journal Article] Photoinduced C(sp 3)-N Bond Cleavage Leading to the Stereoselective Syntheses of Alkenes (2019)
  • Author(s): Ze-Kun Yang, Ning-Xin Xu, Chao Wang, and Masanobu Uchiyama
  • Journal Title: Chemistry A European Journal Volume: 25 Pages: 5433-5439
  • DOI: 10.1002/chem.201900886
  • Peer Reviewed
• [Journal Article] Synthesis of all stereoisomers of monomeric spectomycin A1/A2 and evaluation of their protein SUMOylation-inhibitory activity. (2019)
  • Author(s): Nomura Yusaku、Thuaud Frederic、Sekine Daisuke、Ito Akihiro、Maeda Satoko、Koshino Hiroyuki、Hashizume Daisuke、Muranaka Atsuya、Cruchter Thomas、Uchiyama Masanobu、Ichikawa Satoshi、Matsuda Akira、Yoshida Minoru、Hirai Go、Sodeoka Mikiko
  • Journal Title: Chemistry, A European Journal Volume: 25 Pages: 8387-8392
  • DOI: 10.1002/chem.201901093
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] A solvent-free and vacuum-free melt-processing method to fabricate organic semiconducting layers with large crystal size for organic electronic applications (2019)
  • Author(s): Ribierre Jean-Charles、Li Zhao、Liu Xiao、Lacaze Emmanuelle、Heinrich Benoit、Mery Stephane、Sleczkowski Piotr、Xiao Yiming、Lafolet Frederic、Hashizume Daisuke、Aoyama Tetsuya、Uchiyama Masanobu、Wu Jeong Weon、Zaborova Elena、Fages Frederic、D’Aleo Anthony、Mathevet Fabrice、Adachi Chihaya
  • Journal Title: Journal of Materials Chemistry C Volume: 7 Pages: 3190-3198
  • DOI: 10.1039/c8tc04834g
  • Peer Reviewed
• [Journal Article] Synthetic and Biological Studies of Juglorubin and Related Naphthoquinones. (2019)
  • Author(s): Kamo Shogo、Saito Tatsuo、Kusakabe Yasuha、Tomoshige Shusuke、Uchiyama Masanobu、Tsubaki Kazunori、Kuramochi Kouji
  • Journal Title: The Journal of Organic Chemistry Volume: 84 Pages: 13857-13966
  • DOI: 10.1021/acs.joc.9b02119
  • Peer Reviewed
• [Journal Article] A new route for the efficient metalation of unfunctionalized aromatics (2019)
  • Author(s): Peel Andrew J.、Tezuka Noriyuki、D'Rozario James M.、Uchiyama Masanobu、Wheatley Andrew E. H.
  • Journal Title: Chemical Science Volume: 10 Pages: 3385-3400
  • DOI: 10.1039/c8sc04325f
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Organocopper cross-coupling reaction for C-C bond formation on highly sterically hindered structures (2019)
  • Author(s): Miku Oi, Ryo Takita, Junichiro Kanazawa, Atsuya Muranaka, Chao Wang, and Masanobu Uchiyama
  • Journal Title: Chemical Science Volume: 10 Pages: 6107-6112
  • DOI: 10.1039/c9sc00891h
  • Peer Reviewed / Open Access
• [Journal Article] Cationic axial ligands on sulfur substituted silicon(iv) phthalocyanines: improved hydrophilicity and exceptionally red-shifted absorption into the NIR region (2019)
  • Author(s): Furuyama Taniyuki、Ishii Takashi、Ieda Naoya、Maeda Hajime、Segi Masahito、Uchiyama Masanobu、Nakagawa Hidehiko
  • Journal Title: Chemical Communications Volume: 55 Pages: 7311-7314
  • DOI: 10.1039/c9cc03022k
  • Peer Reviewed
• [Journal Article] Regioselective [2+2+2] cycloaddition reaction using allene-ynes with simple allenes under nickel catalysis. (2019)
  • Author(s): Arai Shigeru、Izaki Arisa、Amako Yuka、Nakajima Masaya、Uchiyama Masanobu、Nishida Atsushi
  • Journal Title: Adv. Syn. Catal. Volume: 361 Pages: 4882-4887
  • DOI: 10.1002/adsc.201900719
  • Peer Reviewed
• [Journal Article] In SituGeneration of Silyl Anion Species through Si-B Bond Activation for the Concerted Nucleophilic Aromatic Substitution of Fluoroarenes (2019)
  • Author(s): Kojima Kumiko、Nagashima Yuki、Wang Chao、Uchiyama Masanobu
  • Journal Title: ChemPlusChem Volume: 84 Pages: 277-280
  • DOI: 10.1002/cplu.201900069
  • Peer Reviewed
• [Journal Article] Aromatic butenolides produced by a soil ascomycete Auxarthron sp. KCB15F070 derived from a volcanic island (2019)
  • Author(s): Kim Jong Won、Son Sangkeun、Kim Gil Soo、Otaka Junnosuke、Miura Yuzuki、Muranaka Atsuya、Uchiyama Masanobu、Lee Jung-Sook、Jang Mina、Ko Sung-Kyun、Takahashi Shunji、Osada Hiroyuki、Jang Jae-Hyuk、Ahn Jong Seog
  • Journal Title: Tetrahedron Letters Volume: 60 Pages: 151227-151227
  • DOI: 10.1016/j.tetlet.2019.151227
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Enantioselective deprotometalation of N,N-dialkyl ferrocenecarboxamides using metal amides (2019)
  • Author(s): Hedidi Madani、Dayaker Gandrath、Kitazawa Yu、Yoshii Tatsuya、Kimura Mutsumi、Erb William、Bentabed-Ababsa Ghenia、Chevallier Floris、Uchiyama Masanobu、Gros Philippe C.、Mongin Florence
  • Journal Title: New Journal of Chemistry Volume: 43 Pages: 14898-14907
  • DOI: 10.1039/c9nj03780b
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Inherent atomic mobility changes in carbocation intermediates during the sesterterpene cyclization cascade (2019)
  • Author(s): Sato Hajime、Mitsuhashi Takaaki、Yamazaki Mami、Abe Ikuro、Uchiyama Masanobu
  • Journal Title: Beilstein Journal of Organic Chemistry Volume: 15 Pages: 1890-1897
  • DOI: 10.3762/bjoc.15.184
  • Peer Reviewed / Open Access
• [Journal Article] Recent Progress in the Synthesis of the Monocarba‐closo‐dodecaborate(-) Anions (2019)
  • Author(s): Kanazawa Junichiro、Kitazawa Yu、Uchiyama Masanobu
  • Journal Title: Chemistry A European Journal Volume: 25 Pages: 9123-9132
  • DOI: 10.1002/chem.201900174
  • Peer Reviewed
• [Journal Article] Recent Advances in the Synthetic Chemistry of Bicyclo[1.1.1]pentane (2019)
  • Author(s): Kanazawa Junichiro、Uchiyama Masanobu
  • Journal Title: Synlett Volume: 30 Pages: 1-11
  • DOI: 10.1055/s-0037-1610314
  • Peer Reviewed
• [Journal Article] Electronic states of 3D aromatic molecules on Au(111) surfaces: adsorption of carboranethiol (2019)
  • Author(s): T. Aoki, Yuta Nakahama, T. Ikeda, M. Shindo, M. Uchiyama, and K. Shudo
  • Journal Title: Journal of Materials Science Volume: 54 Pages: 10249-10260
  • DOI: 10.1007/s10853-019-03598-2
  • Peer Reviewed
• [Journal Article] Efficient Synthesis, Structural Characterization, and Optical Properties of 6H-Dibenzo[b,h]carbazole and Its Derivatives (2019)
  • Author(s): Matsumura Mio、Kawahata Masatoshi、Muranaka Atsuya、Hiraiwa Miyuki、Yamaguchi Kentaro、Uchiyama Masanobu、Yasuike Shuji
  • Journal Title: European Journal of Organic Chemistry Volume: 2019 Pages: 3788-3793
  • DOI: 10.1002/ejoc.201900464
  • Peer Reviewed
• [Journal Article] Analysis of degradation products of nitrogen mustards via hydrophilic interaction liquid chromatography-tandem mass spectrometry (2019)
  • Author(s): Otsuka Mai、Miyaguchi Hajime、Uchiyama Masanobu
  • Journal Title: Journal of Chromatography A Volume: 1602 Pages: 199-205
  • DOI: 10.1016/j.chroma.2019.05.015
  • Peer Reviewed
• [Journal Article] N-Alkynylpyridinium Salts: Highly Electrophilic Alkyne-Pyridine Conjugates as Precursors of Cationic Nitrogen-Embedded Polycyclic Aromatic Hydrocarbons (2018)
  • Author(s): Toriumi Naoyuki、Asano Norihito、Miyamoto Kazunori、Muranaka Atsuya、Uchiyama Masanobu
  • Journal Title: Journal of the American Chemical Society Volume: 140 Pages: 3858-3862
  • DOI: 10.1021/jacs.8b00356
  • Peer Reviewed
• [Journal Article] Simultaneous Edge-on to Face-on Reorientation and 1D Alignment of Small π-Conjugated Molecules Using Room-Temperature Mechanical Rubbing (2018)
  • Author(s): Ribierre Jean-Charles、Tanaka Toshihiko、Zhao Li、Yokota Yuki、Matsumoto Shinya、Hashizume Daisuke、Takaishi Kazuto、Muto Tsuyoshi、Heinrich Beno?t、M?ry St?phane、Mathevet Fabrice、Matsushima Toshinori、Uchiyama Masanobu、Adachi Chihaya、Aoyama Tetsuya
  • Journal Title: Advanced Functional Materials Volume: 28 Pages: 1707038-1707038
  • DOI: 10.1002/adfm.201707038
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] From Aniline to Aryl Ether: A Facile, Efficient and Versatile Synthetic Protocol Employing Mild Conditions (2018)
  • Author(s): Wang Dong-Yu、Yang Ze-Kun、Wang Chao、Zhang Ao、Uchiyama Masanobu
  • Journal Title: Angewandte Chemie International Edition Volume: 57 Pages: 3641-3635
  • DOI: 10.1002/anie.201712618
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Theoretical Study of Sesterfisherol Biosynthesis: Computational Prediction of Key Amino Acid Residue in Terpene Synthase (2018)
  • Author(s): Sato Hajime、Narita Koji、Minami Atsushi、Yamazaki Mami、Wang Chao、Suemune Hironori、Nagano Shingo、Tomita Takeo、Oikawa Hideaki、Uchiyama Masanobu
  • Journal Title: Sci. Rep. Volume: 8 Pages: 2473-2473
  • DOI: 10.1038/s41598-018-20916-x
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] "Dumbbell"- and "Clackers"-Shaped Dimeric Derivatives of Monocarba-closo-dodecaborate (2018)
  • Author(s): Kitazawa Yu、Watanabe Mamoru、Masumoto Yui、Otsuka Mai、Miyamoto Kazunori、Muranaka Atsuya、Hashizume Daisuke、Takita Ryo、Uchiyama Masanobu
  • Journal Title: Angew. Chem. Int. Ed. Volume: 57 Pages: 1501-1504
  • DOI: 10.1002/anie.201710122
  • Peer Reviewed
• [Journal Article] Mechanistic Study on Aryl Exchange Reaction of Diaryl-λ3-iodane with Aryl Iodide (2018)
  • Author(s): Masumoto Yui、Miyamoto Kazunori、Iuchi Takuto、Ochiai Masahito、Hirano Keiichi、Saito Tatsuo、Wang Chao、Uchiyama Masanobu
  • Journal Title: The Journal of Organic Chemistry Volume: 83 Pages: 289-295
  • DOI: 10.1021/acs.joc.7b02701
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Radical Multicomponent Carboamination of [1.1.1]Propellane (2017)
  • Author(s): Kanazawa Junichiro、Maeda Katsuya、Uchiyama Masanobu
  • Journal Title: J. Am. Chem. Soc. Volume: 139 Pages: 17791-17794
  • DOI: 10.1021/jacs.7b11865
  • Peer Reviewed
• [Journal Article] Transition Metal-Free trans-Selective Alkynylboration of Alkynes (2017)
  • Author(s): Nogami Marina、Hirano Keiichi、Kanai Misae、Wang Chao、Saito Tatsuo、Miyamoto Kazunori、Muranaka Atsuya、Uchiyama Masanobu
  • Journal Title: Journal of the American Chemical Society Volume: 139 Pages: 12358-12361
  • DOI: 10.1021/jacs.7b06212
  • Peer Reviewed
• [Journal Article] Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition (2017)
  • Author(s): Sohtome Yoshihiro、Nakamura Genta、Muranaka Atsuya、Hashizume Daisuke、Lectard Sylvain、Tsuchimoto Teruhisa、Uchiyama Masanobu、Sodeoka Mikiko
  • Journal Title: Nat. Commun. Volume: 8 Pages: 14875-14875
  • DOI: 10.1038/ncomms14875
  • Peer Reviewed / Open Access
• [Journal Article] Discovery and mechanistic characterization of selective inhibitors of H2S-producing enzyme:: 3-mercaptopyruvate sulfurtransferase (3MST) targeting active-site cysteine persulfide. (2017)
  • Author(s): K. Hanaoka, K. Sasakura, Y. Suwanai, S. Toma-Fukai, K. Shimamoto, Y. Takano, N. Shibuya, T. Terai, T. Komatsu, T. Ueno, Y. Ogasawara, Y. Tsuchiya, Y. Watanabe, H. Kimura, C. Wang, M. Uchiyama, H. Kojima, T. Okabe, Y. Urano, T. Shimizu, T. Nagano
  • Journal Title: Sci. Rep Volume: 7 Pages: 40227-40227
  • DOI: 10.1038/srep40227
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] One-step Conversion of Levulinic Acid to Succinic Acid Using I2 / t-BuOK System: The Iodoform Reaction Revisited (2017)
  • Author(s): Kawasumi Ryosuke、Narita Shodai、Miyamoto Kazunori、Tominaga Ken-ichi、Takita Ryo、Uchiyama Masanobu
  • Journal Title: Sci. Rep. Volume: 7 Pages: 17967-17967
  • DOI: 10.1038/s41598-017-17116-4
  • Peer Reviewed / Open Access
• [Journal Article] Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite (2017)
  • Author(s): Kaga Atsushi、Hayashi Hirohito、Hakamata Hiroyuki、Oi Miku、Uchiyama Masanobu、Takita Ryo、Chiba Shunsuke
  • Journal Title: Angewandte Chemie International Edition Volume: 56 Pages: 11807-11811
  • DOI: 10.1002/anie.201705916
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Effects of N-Oxidation on Heteroaromatic Macrocycles: Synthesis, Electronic Structures, Spectral Properties, and Reactivities of Tetraazaporphyrin meso-N-Oxides (2017)
  • Author(s): Toriumi Naoyuki、Yanagi Shunsuke、Muranaka Atsuya、Hashizume Daisuke、Uchiyama Masanobu
  • Journal Title: Chemistry A European Journal Volume: 23 Pages: 8309-8314
  • DOI: 10.1002/chem.201701300
  • Peer Reviewed
• [Journal Article] Organozinc-Mediated Direct C?C Bond Formation via C?N Bond Cleavage of Ammonium Salts (2017)
  • Author(s): Wang Dong-Yu、Morimoto Koki、Yang Ze-Kun、Wang Chao、Uchiyama Masanobu
  • Journal Title: Chem. Asian J. Volume: 12 Pages: 2554-2557
  • DOI: 10.1002/asia.201701132
  • Peer Reviewed
• [Journal Article] “Naked” Lithium Cation: Strongly Activated Metal Cations Facilitated by Carborane Anions (2017)
  • Author(s): Yu Kitazawa, Ryo Takita, Kengo Yoshida, Atsuya Muranaka, Seijiro Matsubara, Masanobu Uchuyama
  • Journal Title: J. Org. Chem. Volume: 82 Pages: 1931-1935
  • DOI: 10.1021/acs.joc.6b02677
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products (2017)
  • Author(s): Narita, K., Sato, H., Minami, A., Kudo, K., Gao, L., Liu, C., Ozaki, T., Kodama, M.., Lei, X., Taniguchi, T., Monde, K., Yamazaki, M., Uchiyama, M., Oikawa, H.
  • Journal Title: Org. Lett. Volume: 19 Pages: 6696-6699
  • DOI: 10.1021/acs.orglett.7b03418
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea (2017)
  • Author(s): Otaka Junnosuke、Hashizume Daisuke、Masumoto Yui、Muranaka Atsuya、Uchiyama Masanobu、Koshino Hiroyuki、Futamura Yushi、Osada Hiroyuki
  • Journal Title: Org Lett Volume: 19 Pages: 4030-4033
  • DOI: 10.1021/acs.orglett.7b01784
  • Peer Reviewed
• [Journal Article] Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C?H Nitration of Arenes with Removable Auxiliaries (2017)
  • Author(s): Fan Zhoulong、Li Jie、Lu Heng、Wang Dong-Yu、Wang Chao、Uchiyama Masanobu、Zhang Ao
  • Journal Title: Org. Lett. Volume: 19 Pages: 3199-3202
  • DOI: 10.1021/acs.orglett.7b01297
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Revisitation of Organoaluminum Reagents Affords a Versatile Protocol for C?X (X = N, O, F) Bond-Cleavage Cross-Coupling: A Systematic Study (2017)
  • Author(s): Ogawa Hiroyuki、Yang Ze-Kun、Minami Hiroki、Kojima Kumiko、Saito Tatsuo、Wang Chao、Uchiyama Masanobu
  • Journal Title: ACS Catal. Volume: 7 Pages: 3988-3994
  • DOI: 10.1021/acscatal.7b01058
  • Peer Reviewed
• [Journal Article] Quasi-Phase Diagrams at Air/Oil Interfaces and Bulk Oil Phases for Crystallization of Small-Molecular Semiconductors by Adjusting Gibbs Adsorption (2017)
  • Author(s): Watanabe Satoshi、Ohta Takahisa、Urata Ryota、Sato Tetsuya、Takaishi Kazuto、Uchiyama Masanobu、Aoyama Tetsuya、Kunitake Masashi
  • Journal Title: Langmuir Volume: 33 Pages: 8906-8913
  • DOI: 10.1021/acs.langmuir.7b01603
  • Peer Reviewed
• [Journal Article] Iodoarene-catalyzed Oxidative Transformations Using Molecular Oxygen (2017)
  • Author(s): Miyamoto K.、Yamashita J.、Narita S.、Sakai Y.、Hirano K.、Saito T.、Wang C.、Ochiai M.、Uchiyama M.
  • Journal Title: Chemical Communications Volume: 53 Pages: 9781-9784
  • DOI: 10.1039/c7cc05160c
  • Peer Reviewed
• [Journal Article] Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives (2017)
  • Author(s): Matsumura Mio、Yamada Mizuki、Muranaka Atsuya、Kanai Misae、Kakusawa Naoki、Hashizume Daisuke、Uchiyama Masanobu、Yasuike Shuji
  • Journal Title: Beilstein J. Org. Chem. Volume: 13 Pages: 2304-2309
  • DOI: 10.3762/bjoc.13.226
  • Peer Reviewed
• [Journal Article] Water-tunable dual fluorescence based on solvatochromism and nanoaggregation: A highly sensitive visualization and quantification of water (2017)
  • Author(s): Masaru Tanioka, Shinichiro Kamino, Atsuya Muranaka, Yoshinao Shirasaki, Yousuke Ooyama, Masashi Ueda, Masanobu Uchiyama, Shuichi Enomoto, and Daisuke Sawada
  • Journal Title: Phys. Chem. Phys. Chem. Volume: 19 Pages: 1209-1216
  • DOI: 10.1039/c6cp06808a
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Ethereal C–O Bond Cleavage Mediated by Ni(0)-Ate Complex: A DFT Study (2017)
  • Author(s): Kumiko Kojima、Ze-Kun Yang、Chao Wang,、Masanobu Uchiyama
  • Journal Title: CHEMICAL & PHARMACEUTICAL BULLETIN Volume: 65 Issue: 9 Pages: 862-868
  • DOI: 10.1248/cpb.c17-00487
  • NAID: 130006038328
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] Unexpected formation of benziphthalocyanine dimer: An easily synthesizable dimer of phthalocyanine analogue (2017)
  • Author(s): Toriumi Naoyuki、Muranaka Atsuya、Hashizume Daisuke、Uchiyama Masanobu
  • Journal Title: Tetrahedron Letters Volume: 58 Pages: 2267-2271
  • DOI: 10.1016/j.tetlet.2017.04.089
  • Peer Reviewed
• [Book] 薬学研究 (2017)
  • Author(s): 内山 真伸
  • Total Pages: 170
  • Publisher: 東京化学同人
  • ISBN: 9784807917228
• [Remarks] 東京大学大学院薬学系研究科 基礎有機化学教室 HP
  • URL: http://www.f.u-tokyo.ac.jp/~kisoyuki/publication.html