Hanaya, Kengo

写真a

Affiliation

Faculty of Pharmacy, Department of Pharmaceutical Sciences 有機薬化学講座 （Shiba-Kyoritsu）

Position

Assistant Professor/Senior Assistant Professor
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Academic Degrees 【 Display / hide 】

  • 博士（薬学）, Tokyo University of Science, Coursework, 2012.03

    Design and Synthesis of Biomedical Tools and Metalloprotease Inhibitors Based on Chemical Properties of 8-Quinolinol and Their Sulfonates

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Papers 【 Display / hide 】

  • Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

    Fujita R., Hanaya K., Sugai T., Higashibayashi S.

    Scientific Reports （Scientific Reports)  11 （ 1 ）  2021.12

    Research paper (scientific journal), Accepted

    　View Summary

    Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.

  • Metal-free thermal organocatalytic pinacol coupling of arylaldehydes using an isonicotinate catalyst with bis(pinacolato)diboron

    Yasui M., Hanaya K., Sugai T., Higashibayashi S.

    RSC Advances （RSC Advances)  11 （ 40 ） 24652 - 24655 2021.07

    Research paper (scientific journal), Accepted

    　View Summary

    The metal-free thermal organocatalytic pinacol coupling of arylaldehydes has been developed. The intermolecular coupling of arylaldehydes catalyzed byt-butyl isonicotinate with bis(pinacolato)diboron as the co-reducing agent afforded 1,2-diphenylethane-1,2-diols. This reaction was also applicable to the intramolecular coupling of 1,1′-biphenyl-2,2′-dicarbaldehydes to afford 9,10-dihydrophenanthrene-9,10-diols. Various functional groups were tolerated under this coupling condition.

  • Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract

    Hashimoto R., Iai H., Fujita R., Hanaya K., Higashibayashi S., Inoue H., Sugai T.

    Bioscience, biotechnology, and biochemistry （Bioscience, biotechnology, and biochemistry)  85 （ 3 ） 476 - 480 2021.02

    Research paper (scientific journal), Accepted

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    Caffeic acid β-phenethyl ester (CAPE), an antioxidative bioactive catechol isolated from propolis, was semisynthesized from chlorogenic acid and related compounds in an extract of raw (unroasted) Robusta coffee (Coffea canephora) beans in 5 steps and a total yield of 31%. Oxidative degradation of the intermediates and target molecule was prevented by alkaline hydrolysis of the chlorogenic acids in the presence of sodium dithionite (Na2S2O4) and deprotection of the catecholic diacetate precursor by Candida antarctica lipase B-mediated transesterification as the final step.

  • Selective capture and non-invasive release of cells using a thermoresponsive polymer brush with affinity peptides

    Nagase K., Shimura M., Shimane R., Hanaya K., Yamada S., Akimoto A.M., Sugai T., Kanazawa H.

    Biomaterials Science （Biomaterials Science)  9 （ 3 ） 663 - 674 2021.02

    Research paper (scientific journal), Accepted,  ISSN  20474830

    　View Summary

    Tissue engineering and cell transplantation therapy have become promising therapies for intractable diseases. These approaches require cell separation technology without cell modification. Accordingly, in this study, we developed a novel cell separation method using a thermoresponsive block copolymer brush with an affinity peptide. A block copolymer brush with bottom poly(2-hydroxyethyl methacrylate [HEMA]-co-propargyl acrylate) and top poly(N-isopropylacrylamide-co-HEMA) segments was prepared through two steps of atom transfer radical polymerization. Then, cell affinity peptides were conjugated to the bottom segment of the copolymer brush through a click reaction. Using cRGD as a cell-Affinity peptide, enhancement of cell adhesion with rapid adhesion on the copolymer brush was observed at 37 °C, whereas the copolymer brush without cRGD did not exhibit cell adhesion. Temperature-modulated cell adhesion and detachment were performed with a relatively long upper segment because the affinity between peptides and cells was modulated by the swelling and shrinking of the upper thermoresponsive segment. Selective endothelial cell adhesion was performed at 37 °C using GGGREDV as an affinity peptide. Smooth muscle cells and fibroblasts did not adhere to the copolymer brush. Adhered human umbilical vein endothelial cells (HUVECs) were successfully recovered by reducing the temperature to 20 °C. Based on the properties of the copolymer brush, HUVECs could be purified using a mixture of cells simply by changing the temperature. These results demonstrated that the prepared copolymer brush with cell affinity peptides could be a useful cell separation tool because the cells could be separated with specificity and without cell modification using a simple procedure.

  • Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

    Sugai T., Hanaya K., Higashibayashi S.

    Bioscience, biotechnology, and biochemistry （Bioscience, biotechnology, and biochemistry)  85 （ 1 ） 143 - 147 2021.01

    Research paper (scientific journal), Accepted

    　View Summary

    Prunetin (4',5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6'-acetoxy-2',4″-dihydroxy-4'-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

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

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Presentations 【 Display / hide 】

  • ヨウ素を酸化剤とする炭素-窒素結合形成反応を利用したトリプトファン化学修飾法の開拓

    渡邉 俊佑, 東林 修平, 須貝威, 花屋 賢悟

    第65回日本薬学会関東支部大会, 

    2021.09
    , 

    Poster presentation

  • 銅(II)を用いたペプチドN末端化学修飾法の開拓

    八本　果歩, 東林　修平, 須貝　威, 花屋　賢悟

    第65回日本薬学会関東支部大会, 

    2021.09
    , 

    Oral presentation (general)

  • 銅(II)イオンを用いたアルドール反応による N末端アミノ酸選択的化学修飾法の開発

    花屋 賢悟, 八本 果歩, 東林 修平, 須貝 威

    第15回バイオ関連化学シンポジウム, 

    2021.09
    , 

    Oral presentation (general)

  • C–X bond formations for selective chemical modification of biopolymers via nickel(II)-mediated coupling reaction

    Kengo Hanaya, Mary K. Miller, Jun Ohata, Alicia E. Mangubat-Medina, Zachary T. Ball

    21th Tetrahedron Symposium, 

    2021.06
    , 

    Poster presentation

  • ボロン酸を活用した生体高分子の化学修飾

    花屋賢悟

    ２０１９年度若手研究者のためのセミナー, 

    2019.08
    , 

    Public lecture, seminar, tutorial, course, or other speech

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

  • 一時的配向基を用いた遷移金属触媒反応によるタンパク質ペプチド結合の化学修飾

    2021.04
    -
    2024.03

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

  • ボロン酸を用いるクロスカップリング反応を基盤としたタンパク質化学修飾法の開発

    2019.04
    -
    2021.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Early-Career Scientists , Principal investigator

  • スルホン酸エステルを母核とした刺激応答性リンカーの開発とプロドラッグへの応用

    2016.04
    -
    2019.03

    JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE, Grant-in-Aid for Scientific Research, KENGO HANAYA, Research grant, No Setting

  • 刺激応答性リンカーの創製に向けたアミノスルホン酸エステルの分子内環化反応の開発

    2016.04
    -
    2017.03

    THE JAPAN SCIENCE SOCIETY, SASAKAWA SCIENTIFIC RESEARCH GRANT, KENGO HANAYA, Research grant, Principal investigator

  • 酵素触媒を活用した不斉誘導体化試薬の創製 （超高感度化と効率的供給法の開発）

    2015.04
    -
    2016.03

    日本私立学校振興・共済事業団, The Science Research Promotion Fund, Kengo Hanaya, Principal investigator

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Courses Taught 【 Display / hide 】

  • STUDY OF MAJOR FIELD: (ORGANIC AND BIOCATALYTIC CHEMISTRY)

    2022

  • SEMINAR: (ORGANIC AND BIOCATALYTIC CHEMISTRY)

    2022

  • RESEARCH FOR BACHELOR'S THESIS 1

    2022

  • RESEARCH APPARATUS LABORATORY COURSE

    2022

  • PHARMACEUTICAL-ENGLISH SEMINAR

    2022

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