Updated on 2025/07/07

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写真a

 
Raku Irie
 
Organization
School of Science Department of Science Assistant Professor
Title
Assistant Professor
Profile
主に海洋生物由来の生物活性物質を対象とし、その化学構造と作用機序について研究を行っています。
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Degree

  • 修士 (理学) ( 東京大学 )

  • Ph. D. ( The University of Tokyo )

Research Interests

  • Natural Products Chemistry

Research Areas

  • Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules

  • Life Science / Aquatic life science

Education

  • The University of Tokyo (Prof. Shigeki Matsunaga)   Graduate School of Agricultural and Life Sciences   Department of Aquatic Bioscience

    - 2018

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  • The University of Tokyo (Prof. Kazuo Tachibana)   Graduate School of Science   Department of Chemistry

    - 2015

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  • The University of Tokyo   School of Science   Department of Chemistry

    - 2013

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Research History

  • Yokohama City University   Institute of Natural Science, Association of International Arts and Sciences   Assistant Professor

    2018.9

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  • Japan Society for the Promotion of Science   Research Fellowship for Young Scientists (PD)

    2018.4 - 2018.8

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  • Japan Society for the Promotion of Science   Research Fellowship for Young Scientists (DC2)

    2017.4 - 2018.3

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Professional Memberships

  • THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN

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  • THE CHEMICAL SOCIETY OF JAPAN

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  • THE JAPANESE SOCIETY OF FISHERIES SCIENCE

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Papers

  • Fragmentation Analysis of α-Pinene Oxidation Products Using High-Resolution Collision-Induced Dissociation Mass Spectrometry for Application to Functional Group Prediction in Monoterpene Oxidation Products without Chromatography Reviewed

    Daisuke Fukuyama, Raku Irie, Kanako Sekimoto

    Journal of the American Society for Mass Spectrometry   2025.6

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jasms.5c00059

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  • 1,6-Digalloyl glucose in <i>Emblica officinalis</i> increases the proliferation of human keratinocytes and fibroblasts with upregulated expression of periostin Reviewed

    Yoshimi Yamakami, Kyoko Morino, Robert A Kanaly, Raku Irie, Masato Oikawa, Yuki Takauji, Kensuke Miki, Mohammad Nazir Hossain, Dai Ayusawa, Michihiko Fujii

    Bioscience, Biotechnology, and Biochemistry   2025.5

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    Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    Keratinocytes and fibroblasts are the major cell types in the epidermis and the dermis, respectively. Since both cells play important roles in wound healing, compounds that regulate their proliferation are expected to be beneficial to epidermal health. We have previously shown that the extract of Emblica officinalis, which is a well-known herb in Ayurvedic traditional medicine, increases the proliferation of keratinocytes. Here we purified a compound that increased cell proliferation from E. officinalis extract. Through liquid chromatography electrospray ionization tandem mass spectrometry and NMR techniques, the compound was determined to be 1,6-digalloyl glucose. Consistent with this, tannic acid, a type of polygalloyl glucose, also increased cell proliferation. We further found that E. officinalis extract increased the proliferation of fibroblasts as well and showed that it increased cell proliferation at least partly through upregulating the expression of periostin. These findings revealed the mechanism by which E. officinalis extract regulates cell proliferation.

    DOI: 10.1093/bbb/zbaf068

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  • A practical and versatile synthetic strategy for homogeneous polymers of 1,3-propanediamine Reviewed

    Taiga Ohnishi, Raku Irie, Makoto Inai, Toshiyuki Kan, Masato Oikawa

    Bulletin of the Chemical Society of Japan   98 ( 3 )   uoae014   2025.3

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    Authorship:Corresponding author   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/bulcsj/uoaf014

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  • Synthetic Studies on Poecillastrin C: Synthesis of the C14–C35 Segment of the Macrolide Ring Model Reviewed

    Hugh Clark, Yuzuki Takahashi, Tadashi Yoneyama, Yu Suyama, Raku Irie, Masato Oikawa, Seijiro Hosokawa

    The Journal of Organic Chemistry   90 ( 6 )   2362 - 2371   2025.2

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.4c02885

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  • A One‐Pot Conversion of <i>N</i>‐Ns to <i>N</i>‐Boc Group in Polyamine Synthesis Reviewed

    Ryoya Wakabayashi, Taiga Ohnishi, Raku Irie, Masato Oikawa

    ChemistrySelect   10 ( 4 )   e202406118   2025.1

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    Abstract

    We report herein an efficient synthesis of fully Boc‐protected, up to 13‐meric polymer of 1,3‐propanediamine. The synthesis was facilitated by one‐pot conversion of (up to six) N‐Ns groups to N‐Boc groups under conditions of 1) PhSH and Cs<sub>2</sub>CO<sub>3</sub> for deprotection of the Ns group, followed by 2) Boc<sub>2</sub>O for Boc protection. The average yield per Ns group was extremely high, especially for substrates with four to six Ns groups (94.6%–96.6%).

    DOI: 10.1002/slct.202406118

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  • Stereochemical Assignment of the 36-Membered Macrolide Ring Portion of Poecillastrin C Reviewed

    Raku Irie, Yuki Hitora, Ryuichi Watanabe, Hugh Clark, Yu Suyama, Shinji Sekiya, Toshiyuki Suzuki, Kentaro Takada, Shigeki Matsunaga, Seijiro Hosokawa, Masato Oikawa

    Organic Letters   26 ( 25 )   5290 - 5294   2024.6

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.4c01632

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  • Total synthesis of lycoperdic acid and stereoisomers (part 1): Double asymmetric hydrogenation of a racemic enamide Reviewed

    Kenji Morokuma, Kento Tanaka, Raku Irie, Masato Oikawa

    Tetrahedron   146   133622   2023.10

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.tet.2023.133622

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  • Total synthesis of lycoperdic acid and stereoisomers (part 2): Completion of the synthesis and biological evaluation Reviewed

    Kenji Morokuma, Hiromi Watari, Maika Mori, Ryuichi Sakai, Raku Irie, Masato Oikawa

    Tetrahedron   145   133623   2023.9

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.tet.2023.133623

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  • Synthesis of a fully protected long-chain polyamine subunit of aculeine B using the photoremovable NPEC group Reviewed

    Masayoshi Miyahara, Ryoya Wakabayashi, Raku Irie, Masato Oikawa

    Organic & Biomolecular Chemistry   21 ( 17 )   3636 - 3643   2023

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    A protected dodecameric polymer of 1,3-propanediamine was synthesized by the Ns strategy. Versatility of the NPEC protecting group is also reported.

    DOI: 10.1039/d3ob00369h

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  • Synthetic Studies on the Initially Proposed Structure of Protoaculeine B: Discovery of Neuronally Active Heterotricyclic Amino Acids Reviewed

    Kazunori Otsuka, Masayoshi Miyahara, Sara Takaki, Ryoya Wakabayashi, Kei Miyako, Raku Irie, Satoshi Takamizawa, Ryuichi Sakai, Masato Oikawa

    European Journal of Organic Chemistry   2022 ( 36 )   e202200669   2022.9

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ejoc.202200669

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202200669

  • Oxa-Michael-based divergent synthesis of artificial glutamate analogs Reviewed

    Shuntaro Tsukamoto, Oriel Hlokoane, Kei Miyako, Raku Irie, Ryuichi Sakai, Masato Oikawa

    RSC Advances   12 ( 34 )   22175 - 22179   2022

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    By interchanging the order of reactions, two types of skeletons were created and a neuroactive artificial glutamate analog was developed.

    DOI: 10.1039/D2RA03744K

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  • Stereoselective Formation of cis-Trisubstituted 1,3-Dioxanes Reviewed

    Oriel Hlokoane, Shuntaro Tsukamoto, Raku Irie, Masato Oikawa

    Chemistry Letters   50 ( 8 )   1464 - 1466   2021.8

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.210241

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  • Structure Revision of Protoaculeine B, a Post-translationally Modified N-Terminal Residue in the Peptide Toxin Aculeine B Reviewed International journal

    Raku Irie, Kei Miyako, Satoko Matsunaga, Ryuichi Sakai, Masato Oikawa

    Journal of Natural Products   84 ( 4 )   1203 - 1209   2021.3

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    The structure of protoaculeine B, the N-terminal residue of the marine peptide toxin aculeine B, is revised to the cis-1,3-disubstituted tetrahydro-β-carboline framework. We prepared two truncated model compounds that lack a long-chain polyamine using the one-step Pictet-Spengler reaction of tryptophan and compared their NMR, mass spectra, and chemical reactivity with those of the natural protoaculeine B. The synthetic models reproduced the profiles of the natural product well, which confirmed the appropriateness of the structure revision.

    DOI: 10.1021/acs.jnatprod.0c01280

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  • Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs Reviewed

    Kenji Morokuma, Shuntaro Tsukamoto, Kyosuke Mori, Kei Miyako, Ryuichi Sakai, Raku Irie, Masato Oikawa

    Beilstein Journal of Organic Chemistry   17   540 - 550   2021.2

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    Publishing type:Research paper (scientific journal)   Publisher:Beilstein Institut  

    Herein, we report the enantiospecific synthesis of two artificial glutamate analogs designed based on IKM-159, an antagonist selective to the AMPA-type ionotropic glutamate receptor. The synthesis features the chiral resolution of the carboxylic acid intermediate by the esterification with ʟ-menthol, followed by a configurational analysis by NMR, conformational calculation, and X-ray crystallography. A mice in vivo assay showed that (2<italic>R</italic>)-MC-27, with a six-membered oxacycle, is neuroactive, whereas the (2<italic>S</italic>)-counterpart is inactive. It was also found that TKM-38, with an eight-membered azacycle, is neuronally inactive, showing that the activity is controlled by the ring C.

    DOI: 10.3762/bjoc.17.48

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    Other Link: https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-48.pdf

  • Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata Reviewed

    Masayuki Satake, Raku Irie, Patrick T. Holland, D Tim Harwood, Feng Shi, Yoshiyuki Itoh, Fumiaki Hayashi, Huiping Zhang

    Toxins   13 ( 2 )   82 - 82   2021.1

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    Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    Two different types of polycyclic ether toxins, namely brevisulcenals (KBTs) and brevisulcatic acids (BSXs), produced by the red tide dinoflagellate Karenia brevisulcata, were the cause of a toxic incident that occurred in New Zealand in 1998. Four major components, KBT-F, -G, -H, and -I, shown to be cytotoxic and lethal in mice, were isolated from cultured K. brevisulcata cells, and their structures were elucidated by spectroscopic analyses. New analogues, brevisulcenal-A1 (KBT-A1) and brevisulcenal-A2 (KBT-A2), toxins of higher polarity than that of known KBTs, were isolated from neutral lipophilic extracts of bulk dinoflagellate culture extracts. The structures of KBT-A1 and KBT-A2 were elucidated as sulfated analogues of KBT-F and KBT-G, respectively, by NMR and matrix-assisted laser desorption/ionization tandem mass spectrometry (MALDI TOF/TOF), and by comparison with the spectra of KBT-F and KBT-G. The cytotoxicities of the sulfate analogues were lower than those of KBT-F and KBT-G.

    DOI: 10.3390/toxins13020082

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  • Total Synthesis of the Proposed Structure for Protoaculeine B, a Polycationic Marine Sponge Metabolite, with a Homogeneous Long-Chain Polyamine Reviewed International journal

    Raku Irie, Masayoshi Miyahara, Shota Nakamura, Akito Honda, Ryuichi Sakai, Masato Oikawa

    Journal of Natural Products   83 ( 9 )   2769 - 2775   2020.9

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    By establishing the procedures for sequential deprotections, reaction monitoring, purification, and handling, for the first time, we achieved the total synthesis of the proposed structure for protoaculeine B (2), which is a highly hydrophilic and polycationic amino acid. The NMR and mass spectra and chemical reactivity of the synthetic sample differed from those of natural protoaculeine B, which indicates the necessity for revision of the originally reported structure.

    DOI: 10.1021/acs.jnatprod.0c00761

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  • Hybrid Strategy of sp<sup>3</sup>-Rich Scaffolds for Neuroactive Agents Reviewed

    Masato Oikawa, Shuntaro Tsukamoto, Kenji Morokuma, Raku Irie, Minoru Ikoma

    Journal of Synthetic Organic Chemistry, Japan   78 ( 4 )   292 - 303   2020.4

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:The Society of Synthetic Organic Chemistry, Japan  

    DOI: 10.5059/yukigoseikyokaishi.78.292

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  • Four Stereoisomers of 2-Aminomethyl-1-cyclopropanecarboxylic Acid: Synthesis and Biological Evaluation Reviewed

    Masato Oikawa, Yuka Sugeno, Hideyuki Tukada, Yuichi Takasaki, Satoshi Takamizawa, Raku Irie

    Bulletin of the Chemical Society of Japan   92 ( 11 )   1816 - 1823   2019.11

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20190168

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  • An Empirical Model for Stereochemical Control in the Cyclization of Cyclopropanetricarboxylic Acid Esters Reviewed

    Kento Tanaka, Hitomi Manabe, Raku Irie, Masato Oikawa

    Bulletin of the Chemical Society of Japan   92 ( 8 )   1314 - 1323   2019.8

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20190096

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  • Total synthesis of lycoperdic acid and its C4-epimer Reviewed

    Kenji Morokuma, Raku Irie, Masato Oikawa

    Tetrahedron Letters   60 ( 31 )   2067 - 2069   2019.8

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2019.06.067

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  • Poecillastrin H, a Chondropsin-Type Macrolide with a Conjugated Pentaene Moiety, from a Characella sp. Marine Sponge Reviewed International journal

    Rei Suo, Kentaro Takada, Raku Irie, Ryuichi Watanabe, Toshiyuki Suzuki, Yuji Ise, Susumu Ohtsuka, Shigeru Okada, Shigeki Matsunaga

    Journal of Natural Products   81 ( 5 )   1295 - 1299   2018.5

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.8b00180

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  • Poecillastrin E, F, and G, cytotoxic chondropsin-type macrolides from a marine sponge Poecillastra sp. Reviewed

    Raku Irie, Yuki Hitora, Yuji Ise, Shigeru Okada, Kentaro Takada, Shigeki Matsunaga

    Tetrahedron   74 ( 13 )   1430 - 1434   2018.3

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    Authorship:Lead author   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2018.01.037

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  • Brevisulcenal-G, -H, and –I, Polycyclic Ether Marine Toxins from the Dinoflagellate Karenia brevisulcata Reviewed

    Masayuki Satake, Raku Irie, Yuka Hamamoto, Kazuo Tachibana, Patrick T. Holland, D. Tim Harwood, Feng Shi, Veronica Beuzenberg, Yoshiyuki Itoh, Fumiaki Hayashi, Huiping Zhang

    HETEROCYCLES   96 ( 12 )   2096 - 2096   2018

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/com-18-14014

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  • Resolution of the Confusion in the Assignments of Configuration for the Ciliatamides, Acylated Dipeptides from Marine Sponges Reviewed

    Kentaro Takada, Raku Irie, Rei Suo, Shigeki Matsunaga

    Journal of Natural Products   80 ( 10 )   2845 - 2849   2017.10

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.7b00684

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  • Structure Revision of Poecillastrin C and the Absolute Configuration of the β-Hydroxyaspartic Acid Residue Reviewed

    Raku Irie, Kentaro Takada, Yuji Ise, Susumu Ohtsuka, Shigeru Okada, Kirk R. Gustafson, Shigeki Matsunaga

    Organic Letters   19 ( 19 )   5395 - 5397   2017.9

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    DOI: 10.1021/acs.orglett.7b02835

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  • Brevisulcatic Acids from a Marine Microalgal Species Implicated in a Toxic Event in New Zealand Reviewed

    Raku Irie, Rina Suzuki, Kazuo Tachibana, Patrick T. Holland, D. Tim Harwood, Feng Shi, Paul McNabb, Veronica Beuzenberg, Fumiaki Hayashi, Huiping Zhang, Masayuki Satake

    HETEROCYCLES   92 ( 1 )   45 - 45   2016

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    Authorship:Lead author   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/com-15-13332

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  • Brevisulcatic Acids, Marine Ladder-Frame Polyethers from the Red Tide Dinoflagellate <i>Karenia brevisulcata</i> in New Zealand Reviewed

    Rina Suzuki, Raku Irie, Yanit Harntaweesup, Kazuo Tachibana, Patrick T. Holland, D. Tim Harwood, Feng Shi, Veronica Beuzenberg, Yoshiyuki Itoh, Steven Pascal, Patrick J. B. Edwards, Masayuki Satake

    Organic Letters   16 ( 22 )   5850 - 5853   2014.10

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol502700h

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  • Interaction analysis of a ladder-shaped polycyclic ether and model transmembrane peptides in lipid bilayers by using Förster resonance energy transfer and polarized attenuated total reflection infrared spectroscopy Reviewed

    Kazuya Yamada, Haruki Kuriyama, Toshiaki Hara, Michio Murata, Raku Irie, Yanit Harntaweesup, Masayuki Satake, Seketsu Fukuzawa, Kazuo Tachibana

    Bioorganic & Medicinal Chemistry   22 ( 14 )   3773 - 3780   2014.7

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.bmc.2014.04.044

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MISC

  • Cys間のジスルフィド結合—ペプチドの古くて新しい環化戦略

    入江 樂, 及川 雅人

    化学   79 ( 2 )   68 - 69   2024.2

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    Publisher:化学同人  

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  • Olefin Metathesis

    Journal of Synthetic Organic Chemistry, Japan   78 ( 4 )   365 - 365   2020.4

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    Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (scientific journal)  

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Presentations

  • 長鎖ポリアミンの蛍光標識化と細胞膜透過能の定量的評価

    大西 大河, 入江 樂, 谷 知恵, 稲井 誠, 大内 仁志, 菅 敏幸, 及川 雅人

    第126回有機合成シンポジウム  2025.6  有機合成化学協会

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    Event date: 2025.6

    Presentation type:Poster presentation  

    Venue:京都大学 医薬系総合研究棟 藤多記念ホール  

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  • 多様な鎖長を有する蛍光標識化ポリアミンの合成研究

    大西 大河, 入江 樂, 谷 知恵, 稲井 誠, 大内 仁志, 菅 敏幸, 及川 雅人

    日本化学会第105春季年会  2025.3  日本化学会

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    Event date: 2025.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:関西大学 千里山キャンパス  

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  • 海洋天然物aculeine Aの推定構造に着想を得た、ペプチドのN末端トリプトファン選択的な二重修飾の試み

    向井 崇晃, 入江 樂, 及川 雅人

    日本化学会第105春季年会  2025.3  日本化学会

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    Event date: 2025.3

    Language:Japanese   Presentation type:Poster presentation  

    Venue:関西大学 千里山キャンパス  

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  • 海産毒aculeine Bのペプチド部分AcuPepの構造解析

    入江 樂, 入江 由美, 鈴木 陽茉梨, 小沼 剛, 松永 智子, 酒井 隆一, 池上 貴久, 入江 一浩, 及川 雅人

    第66回天然有機化合物討論会  2024.9 

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    Event date: 2024.9

    Language:Japanese   Presentation type:Poster presentation  

    Venue:同志社大学室町キャンパス 寒梅館  

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  • Aculeine類のペプチド部分AcuPepの構造解析

    入江 樂, 入江 由美, 松永 智子, 酒井 隆一, 入江 一浩, 及川 雅人

    日本化学会第104春季年会  2024.3  日本化学会

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学理工学部 船橋キャンパス  

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  • Multicomponent Synthesis of 4-Iminoimidazolidines and their Bioactivities

    Komoreng Oriel Hlokoane, Raku Irie, Masato Oikawa

    日本化学会第104春季年会  2024.3  日本化学会

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    Event date: 2024.3

    Language:English   Presentation type:Poster presentation  

    Venue:日本大学理工学部 船橋キャンパス  

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  • 蛍光標識化が可能なポリアミン類縁体の効率合成

    大西 大河, 入江 樂, 及川 雅人

    日本化学会第104春季年会  2024.3  日本化学会

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    Event date: 2024.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:日本大学理工学部 船橋キャンパス  

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  • Poecillastrin類の構造解析に向けた分解反応の試み

    入江 樂, 韓 子安, 及川 雅人

    日本化学会第104春季年会  2024.3  日本化学会

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    Event date: 2024.3

    Language:Japanese   Presentation type:Poster presentation  

    Venue:日本大学理工学部 船橋キャンパス  

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  • Lewis Acid-Catalyzed Three-Component Reaction of isocyanides, amines, and aldehydes for the Synthesis of Iminoimidazolidines

    Oriel Hlokoane, Raku Irie, Masato Oikawa

    2023.10 

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    Event date: 2023.10

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  • カイメン共生真菌Fusarium属から単離された新規ポリケチド化合物の構造決定

    赤間 悠哉, 石丸 悠太, 浅野 真希, 入江 樂, 及川 雅人, 周防 玲, 糸井 史朗

    令和5年度日本水産学会春季大会  2023.3  日本水産学会

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Protoaculeine Bおよびaculeine類の固相全合成による構造の確定

    入江 樂, 高木 紗羅, 若林 稜也, 谷 知恵, 松永 智子, 稲井 誠, 大内 仁志, 酒井 隆一, 菅 敏幸, 及川 雅人

    日本化学会第103春季年会  2023.3  日本化学会

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学 野田キャンパス  

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  • クリックケミストリーを基盤としたaculeine人工類縁体の迅速合成と活性評価

    高木 紗羅, 入江 樂, 若林 稜也, 入江 由美, 辺 浩美, 谷 知恵, 松永 智子, 稲井 誠, 大内 仁志, 菅 敏幸, 酒井 隆一, 入江 一浩, 及川 雅人

    日本化学会第103春季年会  2023.3  日本化学会

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学 野田キャンパス  

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  • 海産毒aculeine 類の構造をモチーフとするポリアミン–ペプチド複合体の合成と活性評価

    高木 紗羅, 入江 樂, 若林 稜也, 谷 知恵, 松永 智子, 入江 由美, 稲井 誠, 大内 仁志, 入江 一浩, 酒井 隆一, 菅 敏幸, 及川 雅人

    第83回有機合成化学協会関東支部シンポジウム  2022.11  有機合成化学協会関東支部

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    Event date: 2022.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:新潟薬科大学新津駅東キャンパス  

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  • オキサマイケル反応を用いた人工グルタミン酸類縁体の多様性指向型合成

    塚本 俊太郎, Oriel Hlokoane, 入江 樂, 及川 雅人

    第83回有機合成化学協会関東支部シンポジウム  2022.11  有機合成化学協会関東支部

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    Event date: 2022.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:新潟薬科大学新津駅東キャンパス  

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  • Synthetic studies on aculeines, peptide toxins post-translationally modified by long-chain polyamines Invited International conference

    Raku Irie, Sara Takaki, Ryoya Wakabayashi, Chisato Tani, Hitoshi Ouchi, Makoto Inai, Toshiyuki Kan, Masato Oikawa

    International Congress on Pure & Applied Chemistry Kota Kinabalu (ICPAC Kota Kinabalu 2022)  2022.11 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Country:Malaysia  

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  • 長鎖ポリアミンにより翻訳後修飾を受けたペプチド毒aculeine類の合成研究

    入江 樂, 宮原 正義, 高木 紗羅, 若林 稜也, 谷 知恵, 松永 智子, 入江 由美, 稲井 誠, 大内 仁志, 入江 一浩, 酒井 隆一, 菅 敏幸, 及川 雅人

    第64回天然有機化合物討論会  2022.9 

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    Event date: 2022.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:静岡市清水文化会館マリナート  

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  • Stereochemical analysis of poecillastrin C, a cytotoxic macrolide lactam from marine sponges International conference

    Raku Irie, Yuki Hitora, Ryuichi Watanabe, Shinji Sekiya, Yu Suyama, Hugh Clark, Toshiyuki Suzuki, Kentaro Takada, Seijiro Hosokawa, Masato Oikawa, Shigeki Matsunaga

    The International Chemical Congress of Pacific Basin Societies 2021 (Pacifichem 2021)  2021.12 

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    Event date: 2021.12

    Language:English   Presentation type:Poster presentation  

    Venue:オンライン  

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  • ペプチド-ポリアミン複合型海産毒aculeine類の固相合成研究

    高木 紗羅, 板東 佳努, 入江 樂, 及川 雅人

    第11回 CSJ化学フェスタ2021  2021.10  日本化学会

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    Event date: 2021.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:オンライン  

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  • メンチルエステル化/PGMEアミド化によるキラルなグルタミン酸類縁体の合成研究

    入江 樂, 森 京介, 塚本 俊太郎, 及川 雅人

    日本化学会第101春季年会  2021.3  日本化学会

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    Event date: 2021.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:オンライン  

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  • 翻訳後修飾アミノ酸protoaculeine Bの構造訂正

    入江 樂, 宮古 圭, 松永 智子, 酒井 隆一, 及川 雅人

    日本化学会第101春季年会  2021.3  日本化学会

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    Event date: 2021.3

    Language:Japanese  

    Venue:オンライン  

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  • Pictet-Spengler反応を用いたペプチド-ポリアミン複合型天然物の合成簡略化の試み

    中村 翔太, 入江 樂, 及川 雅人

    第10回 CSJ化学フェスタ2020  2020.10  日本化学会

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    Event date: 2020.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:オンライン  

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  • Divergent Syntheses and Biological Evaluations of New Artificial Glutamate Analogs

    Shuntaro Tsukamoto, Raku Irie, Masato Oikawa

    2020.3 

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    Event date: 2020.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

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  • Studies on N–acyl–β–aminoalcohol-selective deacylation using imidazole chemistry

    Raku Irie, Masato Oikawa

    2020.3 

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    Country:Japan  

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  • Synthetic studies on aculeine B, a peptide–polyamine hybrid marine toxin

    Masayoshi Miyahara, Raku Irie, Ryuichi Sakai, Yumi Irie, Kazuhiro Irie, Masato Oikawa

    2020.3 

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    Event date: 2020.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

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  • 海産ポリアミンprotoaculeine Bの合成研究

    及川 雅人, 宮原 正義, 入江 樂

    反応と合成の進歩シンポジウム  2019.10  日本薬学会 化学系薬学部会

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    Event date: 2019.10

    Language:Japanese   Presentation type:Poster presentation  

    Venue:倉敷市芸文館   Country:Japan  

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  • Search for Marine Natural Products Using Morphology-guided Cell-based Assay

    ○Rei Suo, Kentaro Takada, Hisanori Kohtsuka, Yuji Ise, Raku Irie, Ryuichi Watanabe, Toshiyuki Suzuki, Susumu Ohtsuka, Shigeru Okada, Shigeki Matsunaga

    60th Symposium on the Chemistry of Natural Products  2018.9 

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  • Structure Analysis of Poecillastrins, Cytotoxic Macrolide Lactams from Marine Sponges International conference

    Raku Irie, Kentaro Takada, Yuki Hitora, Yuji Ise, Susumu Ohtsuka, Shigeru Okada, Kirk R. Gustafson, Shigeki Matsunaga

    Gordon Research Conferences (Marine Natural Products)  2018.3 

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  • カイメン由来のリポペプチドciliatamide Aの全合成および立体化学の確定

    高田健太郎, 入江樂, 岡田茂, 松永茂樹

    平成29年度日本水産学会春季大会  2017.3 

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  • Structure Analysis of Poecillastrin Analogs International conference

    Raku Irie, Kentaro Takada, Shigeru Okada, Shigeki Matsunaga

    Gordon Research Conference (Marine Natural Products)  2016.3 

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  • 大島新曽根産カイメン由来 新規poecillastrin類縁体の単離と構造解析

    入江樂, 高田健太郎, 岡田茂, 松永茂樹

    平成28年度日本水産学会春季大会  2016.3 

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  • Structural Elucidation of Ladder-Shaped Polyethers from a Red Tide Dinoflagellate in New Zealand

    ○Irie Raku, Suzuki Rina, Satake Masayuki, Tachibana Kazuo, Harwood Tim, Holland Patrick, Itoh Yoshiyuki

    56th Symposium on the Chemistry of Natural Products  2014.10 

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  • Poecillastra属カイメン由来新規poecillastrin類縁体の単離と構造決定

    周防玲, 高田健太郎, 入江樂, 渡邊龍一, 鈴木敏之, 大塚攻, 岡田茂, 松永茂樹

    平成30年度日本水産学会春季大会  2018.3 

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  • カイメン由来の細胞毒性マクロライドpoecillastrin類の構造訂正

    入江樂, 高田健太郎, 岡田茂, 松永茂樹, 伊勢優史, 大塚攻, GUSTAFSON Kirk R

    平成30年度日本水産学会春季大会  2018.3 

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  • カイメン由来の抗腫瘍性物質poecillastrin類の構造研究

    入江樂, 人羅勇気, 高田健太郎, 岡田茂, 松永茂樹

    第35回メディシナルケミストリーシンポジウム  2017.10 

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  • Structure investigation of poecillastrins International conference

    IRIE Raku, TAKADA Kentaro, OKADA Shigeru, MATSUNAGA Shigeki

    International Symposium “Fisheries Science for Future Generations”  2017.9 

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  • protoaculeine B の合成研究

    宮原 正義, 塩﨑 宏樹, 石川 裕一, 入江 樂, 及川 雅人

    第76回有機合成化学協会関東支部シンポジウム -新潟 (長岡) シンポジウム-  2018.12 

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  • ペプチドーポリアミン複合型海洋天然物の合成研究と生物機能

    宮原 正義, 入江 樂, 及川 雅人

    日本化学会第99春季年会  2019.3 

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  • 人工グルタミン酸類縁体の合成と活性評価

    塚本 俊太郎, 入江 樂, 及川 雅人

    日本化学会第99春季年会  2019.3 

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  • Collective synthesis of cis-fused heterobicycles by oxa-Michael reactions from cis-2-vinylcycloalkan-1-ol

    HLOKOANE Oriel, 入江 樂, 及川 雅人

    日本化学会第99春季年会  2019.3 

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  • 人工iGluRリガンドの不斉合成と構造活性相関

    塚本 俊太郎, 諸熊 賢治, 入江 樂, 及川 雅人

    第76回有機合成化学協会関東支部シンポジウム -新潟 (長岡) シンポジウム-  2018.12 

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  • 天然物の構造解析を志向したN-アシル-β-アミノアルコール選択的な誘導体化の試み

    入江 樂, 及川 雅人

    日本化学会第99春季年会  2019.3 

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  • ペプチドの新奇な翻訳後修飾として見出されたN末端トリプトファン選択的な二重修飾反応

    向井 崇晃, 入江 樂, 及川 雅人

    第88回有機合成化学協会関東支部シンポジウム  2025.5  有機合成化学協会関東支部

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    Venue:工学院大学 新宿キャンパス  

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  • 蛍光標識ポリアミンを用いた細胞膜透過能の鎖長依存性評価

    大西 大河, 入江 樂, 辺 浩美, 谷 知恵, 稲井 誠, 大内 仁志, 菅 敏幸, 酒井 隆一, 及川 雅人

    第88回有機合成化学協会関東支部シンポジウム  2025.5  有機合成化学協会関東支部

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    Venue:工学院大学 新宿キャンパス  

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  • 長鎖ポリアミンにより修飾を受けた海産ペプチドaculeine類の固相合成研究

    高木 紗羅, 入江 樂, 若林 稜也, 谷 知恵, 稲井 誠, 大内 仁志, 松永 智子, 酒井 隆一, 菅 敏幸, 及川 雅人

    第82回有機合成化学協会関東支部シンポジウム  2022.5  有機合成化学協会関東支部

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    Venue:横浜国立大学常盤台キャンパス  

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  • 長鎖ポリアミンの反復合成法の確立と蛍光標識化

    大西 大河, 入江 樂, 及川 雅人

    第86回有機合成化学協会関東支部シンポジウム  2024.5  有機合成化学協会関東支部

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    Venue:東京理科大学野田キャンパス  

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  • Protoaculeine Bの合成研究(1)提唱構造の全合成

    入江 樂, 宮原 正義, 酒井 隆一, 及川 雅人

    第80回有機合成化学協会関東支部シンポジウム  2020.12 

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    Venue:オンライン  

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  • 天然物の構造解析から学んだ有機合成 Invited

    入江 樂

    2021年度若手研究者のためのセミナー  2021.8  有機合成化学協会関東支部

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    Venue:オンライン  

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  • Protoaculeine Bの合成研究(2)簡略化体の合成による構造の訂正

    入江 樂, 宮古 圭, 松永 智子, 酒井 隆一, 及川 雅人

    第80回有機合成化学協会関東支部シンポジウム  2020.12 

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    Venue:オンライン  

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  • 長鎖ポリアミンにより修飾を受けたトリプトファンprotoaculeine Bの全合成

    若林 稜也, 高木 紗羅, 入江 樂, 及川 雅人

    第82回有機合成化学協会関東支部シンポジウム  2022.5  有機合成化学協会関東支部

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    Venue:横浜国立大学常盤台キャンパス  

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  • 固相上でのPictet-Spengler反応を鍵とするaculeine類の合成研究

    高木 紗羅, 若林 稜也, 入江 樂, 及川 雅人

    第81回有機合成化学協会関東支部シンポジウム  2021.11  有機合成化学協会関東支部

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    Venue:オンライン  

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  • 梯子状ポリエーテルと膜貫通ペプチド認識機構の解明

    福沢 世傑, 山田 和哉, 栗山 晴樹, 原 利明, 村田 道雄, 入江 樂, Yanit Harntaweesup, 佐竹 真幸, 橘 和夫

    新規素材探索研究会第13回セミナー  2014.6 

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  • ニュージーランドの赤潮有毒渦鞭毛藻が生産する新規水溶性化合物の単離と構造解析

    入江 樂, 鈴木 里菜, 佐竹 真幸, 橘 和夫, Tim Harwood, Patrick Holland

    新規素材探索研究会第13回セミナー  2014.6 

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  • ニュージーランドの赤潮有毒渦鞭毛藻が生産するポリ環状エーテルの単離と構造解析

    ○IRIE, Raku, SATAKE, Masayuki, TACHIBANA, Kazuo, HARWOOD, Tim, HOLLAND, Patrick

    日本化学会第94春季年会  2014.3 

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Research Projects

  • ポリアミン-ペプチド複合型海産毒の化学合成と膜透過メカニズムの解明

    2025.6 - 2026.3

    蛋白質研究奨励会  金子・成田研究奨励金 

    入江 樂

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\800000 ( Direct Cost: \720000 、 Indirect Cost:\80000 )

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  • 化学合成で紐解くポリアミン-ペプチド複合型海産毒の修飾様式と活性中核構造

    Grant number:23K13849  2023.4 - 2026.3

    日本学術振興会  科学研究費助成事業 若手研究  若手研究

    入江 樂

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    Grant amount:\4550000 ( Direct Cost: \3500000 、 Indirect Cost:\1050000 )

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  • 細胞膜で多彩に機能する有機化合物の合成化学的開発

    Grant number:23K23478  2022.4 - 2026.3

    日本学術振興会  科学研究費助成事業  基盤研究(B)

    及川 雅人, 酒井 隆一, 池上 貴久, 入江 樂, 松永 智子, 塚野 千尋, 入江 一浩

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    Grant amount:\17420000 ( Direct Cost: \13400000 、 Indirect Cost:\4020000 )

    膜透過性化合物を利用した細胞内送達技術は、新しい薬物送達の開発につながる。しかし現存の膜透過性化合物には、透過後の挙動制御や細胞毒性などに問題があり、透過効率やin vivoでの適用に限界がある。
    申請者らは、細胞を致死させることなく高分子を細胞内に送達し得る天然の細胞透過ペプチドaculeine (ACU)を見出した。ACUは、カチオン性の長鎖ポリアミンと中分子ペプチドを持ち、それらが生体膜をかく乱するなどして、近傍の高分子を細胞内に送達する。本研究では、有機合成化学と細胞生物学の手法を用いてACUならびに類縁体を人為的に合成し、「活性構造」を明らかにするとともに細胞内の挙動を解析することにより、生体膜や受容体との新奇な相互作用の機構を紐解くための化学的研究を進めている。これにより、細胞に外部から働きかけて化合物を細胞内に送達する低毒性の新しいドラッグデリバリー素子や、シナプス受容体のモジュレーターの創製につなげる。
    本年度は、pACU-B (LCPA-W') の液相および固相合成に成功した。液相では13量体、固相では12量体LCPAである。また、ACU-D (LCPA-W'-TFPP) の固相合成にも取り組んでいる。現在はモノマーアナログの精製を行っているところである。ACU-B (LCPA-W'-AcuPep) については、クリックケミストリーによるLCPAとAcuPepのコンジュゲート化を進めている。このケースでは、clickable AcuPepを調製し、S-S結合の異性体を分離する。一方で、ACU-B-likeライブラリーを調製するため、複数のclickable LCPAの合成を行っている。

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  • Development of an identification method of functionality from alpha-pinene oxidation using an accurate corona discharge ionization collision-induced dissociation mass spectrometry

    Grant number:21K12223  2021.4 - 2024.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

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    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

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  • 化学反応を駆使した多官能基性天然物の構造と作用機序研究

    Grant number:19K15706  2019.4 - 2023.3

    Japan Society for the Promotion of Science  Grant-in-Aid for Early-Career Scientists 

    IRIE Raku

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    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

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  • 創薬シーズとして有望な天然有機化合物の新規構造決定法の開発

    2019.4 - 2020.3

    YOKOHAMA ACADEMIC FOUNDATION  ACADEMIC GRANT 

    IRIE Raku

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  • 抗腫瘍性物質ポエシラストリン類の構造研究からV-ATPase阻害機構の解明へ

    Grant number:17J08775  2017.4 - 2019.3

    Japan Society for the Promotion of Science  Grant-in-Aid for JSPS Research Fellow 

    IRIE Raku

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    Grant amount:\2100000 ( Direct Cost: \2100000 )

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Teaching Experience

  • 先端科学演習a/先端科学実習a

    2021.10 Institution:横浜市立大学

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  • 課題提案型演習Ba

    2021.4 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 課題提案型演習Aa

    2021.1 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 自然科学実験Ia

    2020.9 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 卒業研究/卒業論文

    2020.4 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 自然科学実験IIa

    2019.4 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 物質計測実験

    2018.10 Institution:横浜市立大学

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    Level:Undergraduate (specialized) 

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  • 基礎化学実験

    2018.10 Institution:横浜市立大学

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    Level:Undergraduate (liberal arts) 

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