Ogura, Akihiro

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry （Yagami）

Position

Assistant Professor/Senior Assistant Professor

Related Websites

External Links
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Profile 【 Display / hide 】

  • 2022~ Senior Assistant Professor, Keio Univ. 2021~ Assistant Professor, Keio Univ. 2016~ Research Associate, Keio Univ. (Prof. Ken-ichi Takao) 2013~ Postdoctoral Fellow, RIKEN (Dr. Katsunori Tanaka) 2013 Ph.D. (Prof. Tohru Fukuyama) 2010~ JSPS Research Fellow, Univ. of Tokyo (Prof. Tohru Fukuyama) 2008~ Graduate School of Pharmaceutical Sciences, Univ. of Tokyo (Prof. Tohru Fukuyama)

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Career 【 Display / hide 】

  • 2010.04
    -
    2013.03

    JSPS, Research Fellow (DC1)

  • 2013.04
    -
    2016.03

    RIKEN, Biofunctional Synthetic Chemistry Laboratory, Postdoctoral Associate

  • 2016.04
    -
    2019.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate

  • 2019.04
    -
    2021.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate

  • 2021.04
    -
    2022.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Assistant Professor

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Academic Background 【 Display / hide 】

  • 2004.04
    -
    2008.03

    The University of Tokyo, Faculty of Pharmaceutical Sciences, Department of Pharmaceutical Sciences

    University, Graduated, Other

  • 2008.04
    -
    2010.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Division of Pharmaceutical Chemistry

    Graduate School, Completed, Master's course

  • 2010.04
    -
    2013.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Division of Pharmaceutical Chemistry

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • 博士（薬学）, The University of Tokyo, Coursework, 2013.03

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Licenses and Qualifications 【 Display / hide 】

  • Drivers License, Non-Professional, 2004.09

  • STEP Eiken, Grade Pre-1, 2005.02

  • Hazardous Materials Engineer's License, Class A, 2005.12

  • The Official Business Skill Test in Book-keeping, 2nd Grade, 2006.06

  • Pharmacist License, 2008.08

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Bio chemistry

  • Life Science / Bioorganic chemistry

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Books 【 Display / hide 】

  • 可視光照射で進行するBirch還元

    小椋　章弘, 化学同人, 2020.12

    Contact page： 60-61 , Accepted

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Papers 【 Display / hide 】

  • Antiproliferative activities through accelerating autophagic flux by basidalin and its analogs in human cancer cells.

    Matagawa T, Sasazawa Y, Agui K, Fujimaki M, Kawano S, Ogura A, Takao KI, Igarashi M, Simizu S

    Bioorganic & medicinal chemistry letters 104   129713 - 129713 2024.03

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  0960-894X

    　View Summary

    Basidalin, isolated from the basidiomycete Leucoagaricus naucina, has previously demonstrated antibacterial and antitumor properties against murine cancer cells in vivo, but its effects on human cancer cells remain unknown. In this study, we found that basidalin possesses antiproliferative activity against human cancer cell lines. To elucidate the antiproliferative mechanism of basidalin, we focused on autophagy. Treatment with basidalin led to an increase in LC3-II expression level, and accelerated autophagic flux through an mTOR-independent pathway. Moreover, according to the structure-activity relationship analysis-including newly synthesized basidalin analogs-the formyl group, not the amino group, contributes to the antiproliferative activities of basidalin against human cancer cells. Additionally, the antiproliferative activity of basidalin analogs was strongly correlated with autophagy-inducing activity, indicating that basidalin exhibits antiproliferative activity through autophagy induction. These data suggest that basidalin, characterized by its ability to upregulate autophagic flux, emerges as a novel anticancer drug.

  • Synthesis of Indoles via Sigmatropic Rearrangements and Olefin Isomerization

    Tomoki Uchida, Ryosuke Saito, Ken‐ichi Takao, Akihiro Ogura

    Advanced Synthesis & Catalysis （Advanced Synthesis and Catalysis)  366 （ 3 ） 465 - 472 2024.02

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  1615-4150

    　View Summary

    Indoles are important heterocycles in pharmaceuticals and agrochemicals, and their atom-economical synthesis is needed. Herein, we describe the synthesis of indoles using sigmatropic rearrangements. The N-allylaniline was oxidized by environmentally benign hydrogen peroxide, and spontaneous [2,3]-Meisenheimer rearrangement gave N-allyloxyaniline. Subsequent treatment with a ruthenium catalyst afforded N-vinyloxyaniline, which underwent [3,3]-sigmatropic rearrangement to give indoles, expelling water as the only byproduct. The whole sequence is free of quantitative salt byproducts, thereby avoiding aqueous work up and cutting off the inorganic waste.

  • Open system synthesis of narrow-bandwidth red-fluorescent carbon quantum dots with a function of multi-metal ion sensing

    Rika Katakami, Kohei Sato, Akihiro Ogura, Ken-ichi Takao, Yoshiki Iso, Tetsuhiko Isobe

    Journal of Materials Chemistry C （Journal of Materials Chemistry C)  11 （ 12 ） 4143 - 4152 2023

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  2050-7526

    　View Summary

    Carbon quantum dots (CQDs) are environmentally friendly phosphors. However, there have been few reports on red-emitting CQDs with narrow-bandwidths, all of which were synthesized via solvothermal methods using autoclaves. Here, red-emitting CQDs were synthesized from 4,6-diaminoresorcinol dihydrochloride (DAR), which is an aromatic compound with electron-donating hydroxy and amino groups. The synthesis involved heating at 180 °C for 6 h in a high-boiling-point 1,2-pentanediol solvent in an open system without using autoclaves and catalysts. The DAR-derived-CQDs in ethanol exhibited red photoluminescence with a 0.14 eV full width at half-maximum that was comparable to that of narrow-bandwidth blue-fluorescent phloroglucinol (PG)-derived-CQDs. The red emission was attributed to a weakened quantum-size effect and electron-donating NH2 groups. The hydroxy groups of PG-derived-CQDs interacted with Al3+ and Fe3+ ions, resulting in fluorescence quenching. DAR-derived-CQDs have hydroxy and amino groups, which facilitate the fluorescence quenching for Al3+, Fe3+, Cu2+, and Pb2+ ions.

  • Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

    Hiroki Yamamoto, Kohei Yamaoka, Ann Shinohara, Kouhei Shibata, Ken-ichi Takao, Akihiro Ogura

    Chemical Science （Chemical Science)  14 （ 40 ） 11243 - 11250 2023

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  2041-6520

    　View Summary

    In organic chemistry, selecting mild conditions for transformations and saving energy are increasingly important for achieving sustainable development goals. Herein, we describe a red-light-mediated Barton decarboxylation using readily available red-light-emitting diodes as the energy source and zinc tetraphenylporphyrin as the catalyst, avoiding explosive or hazardous reagents or external heating. Mechanistic studies suggest that the reaction probably proceeds via Dexter energy transfer between the activated catalyst and the Barton ester. Furthermore, a one-pot wavelength-selective reaction within the visible light range is developed in combination with a blue-light-mediated photoredox reaction, demonstrating the compatibility of two photochemical transformations based on mechanistic differences. This one-pot process expands the limits of the decarboxylative Giese reaction beyond polarity matching.

  • In vivo imaging of fluorescent albumin modified with pyruvylated-human-type complex oligosaccharide reveals sialylation-like biodistribution and kinetics

    Ryoichiro Fukuhara, Akihiro Ogura, Sho Yoshinaga, Takamasa Fukunaga, Takashi Kinoshita, Wataru Sumiyoshi, Yujiro Higuchi, Katsunori Tanaka, Kaoru Takegawa

    Bioorganic & Medicinal Chemistry （Elsevier BV)  70   116943 - 116943 2022.09

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  0968-0896

    　View Summary

    Both pyruvylation and sialylation onto the terminus of oligosaccharides of N-glycoproteins seem to be structurally and functionally similar with a property of conferring negative charge. However, detailed molecular characteristics of pyruvylation and sialylation in vivo were elusive. Here, to investigate an effect of terminal pyruvylation to N-glycan on in vivo biodistribution and kinetics, we prepared human serum albumin (HSA) modified with pyruvylated N-glycan (PvG), conjugated with HiLyte Fluor 750 (FL750-PvGHSA). In vivo imaging by using FL750-PvGHSA revealed that terminally pyruvylated N-glycoalbumin was excreted like sialylated N-glycoalbumin, suggesting that pyruvylation mimics sialylation in in vivo biodistribution and kinetics of N-glycoproteins. Terminal pyruvylation onto N-glycans can be a potential tool for a novel glycoengineering strategy.

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Papers, etc., Registered in KOARA 【 Display / hide 】

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Reviews, Commentaries, etc. 【 Display / hide 】

  • The Stereoselective Construction of All-Carbon Quaternary Stereocenters by Allylations and Its Application to Synthetic Studies of Natural Products

    Akihiro Sakama, Akihiro Ogura, Keisuke Yoshida, Ken-ichi Takao

    Journal of Synthetic Organic Chemistry, Japan (The Society of Synthetic Organic Chemistry, Japan)  78 ( 11 ) 1039 - 1047 2020.11

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0037-9980

  • Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

    Ken-ichi Takao, Akihiro Ogura, Keisuke Yoshida, Siro Simizu

    Synlett (Georg Thieme Verlag {KG})  31 ( 05 ) 421 - 433 2020.02

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0936-5214

    　View Summary

    In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.

    1 Introduction

    2 Total Synthesis of (+)-Pestalotiopsin A

    3 Total Synthesis of (+)-Cytosporolide A

    4 Total Synthesis of (+)-Vibsanin A

    5 Total Syntheses of (+)-Aquatolide and Related Humulanolides

    6 Conclusion

  • Recent Advances in the Total Synthesis of Clavilactones

    Ken-ichi Takao, Akihiro Ogura

    HETEROCYCLES (Japan Institute of Heterocyclic Chemistry)  100 ( 9 ) 1355 - 1355 2020

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0385-5414

  • Next-generation glycocluster for achieving pattern recognition in living system

    Akihiro Ogura, Katsunori Tanaka

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN (SOC SYNTHETIC ORGANIC CHEM JPN)  77 ( 2 ) 163 - 172 2019.02

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Lead author,  ISSN  1883-6526

  • Exploring the glycan interaction in vivo: Future prospects of neo-glycoproteins for diagnostics

    Akihiro Ogura, Almira Kurbangalieva, Katsunori Tanaka

    GLYCOBIOLOGY (OXFORD UNIV PRESS INC)  26 ( 8 ) 804 - 812 2016.08

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0959-6658

    　View Summary

    Herein the biodistributions and in vivo kinetics of chemically prepared neoglycoproteins are reviewed. Chemical methods can be used to conjugate various mono- and oligosaccharides onto a protein surface. The kinetics and organ-specific accumulation profiles of these glycoconjugates, which are introduced through intravenous injections, have been analyzed using conventional dissection studies as well as noninvasive methods such as single photon emission computed tomography, positron emission tomography and fluorescence imaging. These studies suggest that glycan-dependent protein distribution kinetics may be useful for pharmacological and diagnostic applications.

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Presentations 【 Display / hide 】

  • 赤色光照射で駆動する新規ラジカル開始剤の開発

    谷川 麟太郎、篠原 杏、高尾 賢一、小椋 章弘

    2024.03
    , 

    Oral presentation (general)

  • ステルヒルスチンAおよびBの全合成研究

    南 友紀子、野村 亮太、小椋 章弘、高尾 賢一

    日本化学会第104春季年会, 

    2024.03
    , 

    Oral presentation (general)

  • グッチフェロンAの全合成研究

    滝本 美里、七瀧 智俊、小椋 章弘、高尾 賢一

    日本化学会第104春季年会, 

    2024.03
    , 

    Oral presentation (general)

  • ビールショウスキーシンの全合成研究

    寺内 頌、笹田 祥吾、小椋 章弘、高尾 賢一

    第123回有機合成シンポジウム (東京) , 

    2023.11
    , 

    Oral presentation (general)

  • Red-Light-Mediated Radical Reactions and Wavelength-Selective Transformations

    Akihiro Ogura, Ken-ichi Takao

    The 16th Keio LCC-Yonsei CBMH Joint Symposium (横浜) , 

    2023.11
    , 

    Oral presentation (invited, special)

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Research Projects of Competitive Funds, etc. 【 Display / hide 】

  • 水のみを副生成物とするインドール合成による低副作用生体内合成化学治療

    2024.04
    -
    2025.03

    Research grant, Principal investigator

  • High atom-economy low-waste synthesis of heterocycles via [2,3]-sigmatropic rearrangement

    2023.04
    -
    2024.03

    Fujimori Science and Technology Foundation, 2023年度研究助成, Research grant, Principal investigator

  • 可視光の波長制御による複雑骨格のワンポット構築法の開発

    2022.04
    -
    2025.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Principal investigator

    　View Summary

    赤色光は低コストや高エネルギー変換効率、安全性といった明確な利点を有するにもかかわらず、その有機合成化学における利用は見過ごされてきた。本研究では、注目されてこなかったこの未開拓のエネルギー源である赤色光の可能性を最大限引き出し、真に持続可能な社会にふさわしい反応の開発を目指すため、青色光との波長選択的なラジカル反応を実現する。具体的には、赤色光を用いたBarton脱炭酸的官能基化反応の開発、赤色光→青色光の照射によるワンポットでの炭素-炭素結合の自在な生成と切断に取り組み、最終的にはこれらを光フロー反応に展開する。

  • Development of red light-mediated organic reactions

    2019.04
    -
    2021.03

    Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Ogura Akihiro, Grant-in-Aid for Early-Career Scientists, Research grant, Principal investigator

    　View Summary

    We have developed a red light-mediated Barton-McCombie reaction and related reactions. The reaction conditions requires very mild conditions, which can be characterized by a readily available catalyst, ambient temperature and red LED irradiation. Also, we achieved red ligh-mediated decarboxylative Giese reaction to realize carbon-carbon bond cleavage and formation within one operation. Elucidation of reaction mechanism was also conducted.

  • Development of red light-driven organic reactions

    2018.04
    -
    2019.03

    Tobe Maki Foundation, 平成30年度 研究助成, Research grant, Principal investigator

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Courses Taught 【 Display / hide 】

  • ORGANIC CHEMISTRY

    2024

  • LABORATORIES IN BASIC CHEMISTRY

    2024

  • LABORATORIES IN APPLIED CHEMISTRY B

    2024

  • FUNDAMENTAL COMPUTATION IN APPLIED CHEMISTRY

    2024

  • BACHELOR'S THESIS

    2024

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Courses Previously Taught 【 Display / hide 】

  • 現代化学概論

    慶應義塾大学

    2023.10
    , 

    Autumn Semester, Undergraduate (liberal arts), Lecture

  • 応用化学実験B

    Keio University

    2017.04
    -
    Present
    , 

    Spring Semester, Laboratory work/practical work/exercise, Lecturer outside of Keio

  • 基礎化学実験

    Keio University

    2017.04
    -
    Present
    , 

    Autumn Semester, Laboratory work/practical work/exercise, Lecturer outside of Keio

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Academic Activities 【 Display / hide 】

  • 第56回天然物化学談話会　奨励賞受賞講演

    2023.06

    　View Summary

    座長

  • 日本化学会第103春季年会

    2023.03

    　View Summary

    座長

  • 慶應義塾大学国際糖質科学シンポジウム

    2023.02

    　View Summary

    座長

  • 第82回有機合成化学協会関東支部シンポジウム

    2022.05

    　View Summary

    座長

  • 日本化学会第102春季年会

    2022.03

    　View Summary

    座長

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Memberships in Academic Societies 【 Display / hide 】

  • 日本プロセス化学会, 

    2023.06
    -
    Present

  • 日本化学会, 

    2013.11
    -
    Present

  • 日本薬学会, 

    2009.02
    -
    Present

  • 有機合成化学協会, 

    2007.05
    -
    Present
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Committee Experiences 【 Display / hide 】

  • 2023.03
    -
    Present

    将来計画委員, 日本プロセス化学会

  • 2018.12
    -
    2019.05

    第77回関東支部シンポジウム実行委員会, 有機合成化学協会

  • 2017.09
    -
    Present

    世話人, 天然物談話会

  • 2016.11
    -
    Present

    実行委員, 慶應有機化学若手シンポジウム実行委員会

  • 2016.06
    -
    2017.03

    第97春季年会　会場総務委員, 日本化学会

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