Sugai, Takeshi

写真a

Affiliation

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

Position

Professor

Related Websites

External Links
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Career 【 Display / hide 】

  • 1984.04
    -
    1988.03

    東京大学農学部文部教官助手

  • 1988.04
    -
    1993.03

    慶應義塾大学（理工学部）、助手

  • 1991.08
    -
    1992.09

    Research Associate, The Scripps Research Institute

  • 1993.04
    -
    1997.03

    慶應義塾大学（理工学部）、専任講師

  • 1994.10
    -
    1995.03

    茨城大学大学院（生物化学工学特別講義）、非常勤講師

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Academic Background 【 Display / hide 】

  • 1981.03

    The University of Tokyo, Faculty of Agriculture, 農芸化学科

    University, Graduated

  • 1983.03

    The University of Tokyo, Graduate School, Division of Agricultural Science, 農芸化学専門課程

    Graduate School, Completed, Master's course

  • 1984.03

    The University of Tokyo, Graduate School, Division of Agricultural Science, 農芸化学専門課程

    Graduate School, Withdrawal before completion, Doctoral course

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Academic Degrees 【 Display / hide 】

  • 農学　, The University of Tokyo, 1987.06

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Research Areas 【 Display / hide 】

  • Manufacturing Technology (Mechanical Engineering, Electrical and Electronic Engineering, Chemical Engineering) / Catalyst and resource chemical process (Catalyst and Chemical Process)

  • Manufacturing Technology (Mechanical Engineering, Electrical and Electronic Engineering, Chemical Engineering) / Biofunction and bioprocess engineering (Bioengineering)

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Organic Chemistry)

  • Nanotechnology/Materials / Synthetic organic chemistry (Synthetic Chemistry)

  • Life Science / Bioorganic chemistry (Organic Chemistry)

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Books 【 Display / hide 】

  • “Future Directions in Biocatalysis (Second Edition)”

    R. Tsunekawa, K. Hanaya, M. Shoji, T. Sugai, T. Matsuda, ed., Elsevier, 2017.08

    Scope: 279–295

  • “Comprehensive Organic Synthesis II (Second Edition) Volume 2: Additions to C–X Π-Bonds, Part 2”

    T. Sugai, K. Fushuku, P. Knochel, G. A. Molander, eds., Elsevier, 2014.01

    Scope: 512–522

  • Practical Methods for Biocatalysis and Biotransformations

    T. Sugai, A. Fujino, H. Yamaguchi, M. Ikunaka, J. Whittal, P. W. Sutton, eds., Wiley, 2009.12

    Scope: 190-198

  • Glycoscience: Chemistry and Chemical Biology

    T. Sugai, T. Kajimoto, Springer-Verlag GmbH, Berlin Heidelberg New York (B. O. Fraser-Reid, K. Tatsuta, J. Thiem eds.), 2001.12

    Scope: 907-1021

    　View Summary

    単糖類の化学・酵素合成における最近の進歩について解説した。

  • Enzymes in Nonaqueous Solvents; Methods and Protocols, Methods in Biotechnology

    Springer, 2001.10

    Scope: 401-416

    　View Summary

    界面バイオリアクターを用いる、微生物物質変換反応について著者らの成果を中心に解説した。

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Papers 【 Display / hide 】

  • Isorhamnetin promotes 53BP1 recruitment through the enhancement of ATM phosphorylation and protects mice from radiation gastrointestinal syndrome

    Nishiyama Y., Morita A., Tatsuta S., Kanamaru M., Sakaue M., Ueda K., Shono M., Fujita R., Wang B., Hosoi Y., Aoki S., Sugai T.

    Genes （Genes)  12 （ 10 ）  2021.10

    　View Summary

    Flavonoids are a subclass of polyphenols which are attractive, due to possessing various physiological activities, including a radioprotective effect. Tumor suppressor p53 is a primary reg-ulator in the radiation response and is involved in the pathogenesis of radiation injuries. In this study, we revealed that isorhamnetin inhibited radiation cell death, and investigated its action mechanism focusing on DNA damage response. Although isorhamnetin moderated p53 activity, it promoted phosphorylation of ataxia telangiectasia mutated (ATM) and enhanced 53BP1 recruitment in irradiated cells. The radioprotective effect of isorhamnetin was not observed in the presence of ATM inhibitor, indicating that its protective effect was dependent on ATM. Furthermore, iso-rhamnetin-treated mice survived gastrointestinal death caused by a lethal dose of abdominal irra-diation. These findings suggested that isorhamnetin enhances the ATM-dependent DNA repair pro-cess, which is presumably associated with the suppressive effect against GI syndrome.

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

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

    RSC Advanced （RSC Advances)  2021 （ 11 ） 24652 - 24655 2021.08

    Accepted

    　View Summary

    The metal-free thermal organocatalytic pinacol coupling of arylaldehydes has been developed. The intermolecular coupling of arylaldehydes catalyzed by t-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 1,10-biphenyl-2,20-dicarbaldehydes to afford 9,10-dihydrophenanthrene-9,10-diols. Various functional groups were tolerated under this coupling condition.

  • A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum

    Yamasaki N., Iwasaki I., Sakumi K., Hokari R., Ishiyama A., Iwatsuki M., Nakahara M., Higashibayashi S., Sugai T., Imagawa H., Kubo M., Fukuyama Y., Ōmura S., Yamamoto H.

    Chemistry - A European Journal （Chemistry - A European Journal)  27 （ 17 ） 5555 - 5563 2021.03

    Accepted,  ISSN  09476539

    　View Summary

    The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5-dichloro-2H-1,4-oxazin-2-one with 14 a as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine-resistant Plasmodium falciparum.

  • Chemo-enzymatic Semisynthesis of Caffeic Acid β-Phenethyl Ester, an Antioxidative Component in Propolis, from Raw Coffee Beans Extract

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

    Bioscience, Biotechnology and Biochemistry 85   476 - 480 2021.03

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  09168451

  • Nickel(II)-Mediated C−S Cross-Coupling Between Thiols and ortho-Substituted Arylboronic Acid

    Hanaya K., Ohtsu H., Kawano M., Higashibayashi S., Sugai T.

    Asian Journal of Organic Chemistry （Asian Journal of Organic Chemistry)  10 （ 3 ） 582 - 587 2021.03

    Accepted,  ISSN  21935807

    　View Summary

    Herein, we report a C−S cross-coupling reaction between alkyl thiols or aryl thiols and ortho-substituted arylboronic acids that proceeds in the presence of an inexpensive and ligand-free NiCl2 ⋅ 6H2O salt and N-methylmorpholine, a weak base, at 25 °C in air. The presence of coordinating and electron-withdrawing groups at the ortho-position of the arylboronic acids played a crucial role in determining the efficiency of the reaction. X-ray crystallographic analysis revealed that the [NiCl2(DMF)2(H2O)2] complex was formed in-situ. The complex is an excellent precursor of the active nickel species. The reaction offers an extremely mild and operationally convenient method to access a wide variety of alkyl aryl sulfides and diaryl sulfides without using expensive transition metals, such as palladium, gold, and rhodium, and specialized and expensive ligands.

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

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Presentations 【 Display / hide 】

  • Enzyme-assisted syntheses of bioactive compounds, originated from Scripps days

    T. Sugai

    2019 Scripps Korea Society Symposium (Yonsei University, Seoul, Korea) , 

    2019.08
    , 

    Oral presentation (invited, special)

  • New Entries for Transformation of Carbohydrates towards the Synthesis of Bioactive Compounds

    T. Sugai

    2018 Frontiers in Chemical Biology (Hotel Royal Chiao Hsi, Yilan County, Taiwan) , 

    2018.08
    , 

    Oral presentation (invited, special)

  • Enzyme-catalyzed Asymmetric Reduction of Cyclic Ketoesters and Application to Natural Product Synthesis

    T. Sugai, K. Kuwata, R. Tsunekawa, R. Fujita

    The 13th Yonsei CBMH-Keio LCC Joint Symposium (Yonsei University, Seoul, Korea) , 

    2017.10
    , 

    Oral presentation (invited, special)

  • The Complementary and Integrated Chemo-enzymatic Processes for Fine Chemical Syntheses (Invited Lecture)

    T. Sugai, Y. Yamashita, Y. Niitsu, M. Hamada, C. Hiraoka, T. Higashi, M. Shoji

    The 14th Asia Pacific Confederation of Chemical Engineering (Singapore, Singapore) , 

    2012.02
    , 

    Oral presentation (invited, special)

    　View Summary

    カルバ糖およびDHMEQを題材に、リパーゼによる位置および立体選択的変換について最新の成果を報告した。

  • Chemo-enzymatic approaches towards both enatiomers of dehydroxymethylepoxy-quinomicin (DHMEQ) (Selected Oral Presentation)

    T. Sugai, C. Hiraoka, M. Hamada, Y. Niitsu, R. Kobayashi, K. Nakagawara, T. Seki, M. Suzuki, Y. Yamashita, T. Higashi, M. Shoji, K. Umezawa

    10th International Symposium on Biocatalysis and Biotransformations (Giardini Naxos, Italy) , 

    2011.10
    , 

    Oral presentation (general)

    　View Summary

    DHMEQを題材に、リパーゼによる位置および立体選択的変換について最新の成果を報告した。

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

  • 位置・立体選択的反応を鍵段階とする生物活性物質の合成研究

    2019.04
    -
    2022.03

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

  • Efficient organic synthesis utilizing microbial enzyme catalysts

    2014.04
    -
    2017.03

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

    　View Summary

    Complementary and synergistic utilization of enzyme-catalyzed reactions and chemical transformation was studied, toward the efficient synthesis of complex target molecules involving valuable natural and unnatural products. The achievements are shown below. Lipase-catalyzed transesterification proceeded with specific site-selectivity contrasting to chemical transformations, and the syntheses of selinone and astringin, artepillin C became successful. It was revealed that the transesterification under non-aqueous conditions was advantageous for the substrates which are labile to water and/or prone to protonation under aqueous conditions. The preparation of highly enantiomerically pure (R)-3-hydroxy-N-methylpiperidine by the lipase-catalyzed kinetic resolution of corresponding racemate was established. The synthesis of enantiomers of NMB carboxylic acid was also successful, by discriminating he stereochemistry of remote chiral center in a primary acetate, as the key step.

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Awards 【 Display / hide 】

  • 化学教育賞

    須貝 威, 2021.03, 日本化学会, 高校生から大学生までを惹きつける生物有機化学と実験

    Type of Award： Award from Japanese society, conference, symposium, etc.

  • 有機合成化学協会賞

    須貝 威, 2020.02, 有機合成化学協会, 酵素触媒の選択性を活用した有用物質合成法の開拓

    Type of Award： Award from Japanese society, conference, symposium, etc.

  • Presidential 2000 Green Chemistry Challenge Award, as a co-recipient of the honoring C.-H. Wong

    Takeshi Sugai, 2000.06, Department of Environmental Protection, USA,, Enzymes in Large-scale Organic Synthesis

    Type of Award： Other

  • 農芸化学奨励賞

    須貝 威, 1994.04, 日本農芸化学会, 生体触媒を利用する不斉合成と物質生産への応用

    Type of Award： Award from Japanese society, conference, symposium, etc.

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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

  • PHARMACEUTICAL-ENGLISH SEMINAR

    2022

  • PHARMACEUTICAL CHEMISTRY AND MATERIALS

    2022

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Social Activities 【 Display / hide 】

  • 化学情報協会

    2001.04
    -
    2002.03
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Memberships in Academic Societies 【 Display / hide 】

  • Current Organic Synthesis, 

    2003.01
    -
    Present

  • Mini-Reviews in Organic Chemistry, 

    2003.01
    -
    Present

  • 日本化学会, 

    2004.04
    -
    Present

  • 日本農芸化学会, 

    2001.03
    -
    Present

  • 日本糖質学会, 

    1999.04
    -
    Present

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Committee Experiences 【 Display / hide 】

  • 2003.01
    -
    Present

    Editorial Advisory Board, Current Organic Synthesis

  • 2003.01
    -
    Present

    Editorial Advisory Board, Mini-Reviews in Organic Chemistry

  • 2004.04
    -
    Present

    化学教育協議会大学入試21WG委員, 日本化学会

  • 2001.03
    -
    Present

    日本農芸化学会誌編集幹事, 日本農芸化学会

  • 1999.04
    -
    Present

    評議員, 日本糖質学会

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