Kyushu University Academic Staff Educational and Research Activities Database
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Go Hirai Last modified date:2019.03.26



Graduate School
Undergraduate School


E-Mail
Homepage
http://sekkei.phar.kyushu-u.ac.jp/
Phone
092-642-6603
Fax
092-642-6603
Academic Degree
Ph. D.
Country of degree conferring institution (Overseas)
No
Field of Specialization
Synthetic Organic Chemistry, Natural Products Chemistry、Bioorganic Chemistry
ORCID(Open Researcher and Contributor ID)
0000-0003-3420-555X
Total Priod of education and research career in the foreign country
00years00months
Research
Research Interests
  • Development of nove bioactive molecules based on oxygenated phyto-steroids
    keyword : oxygenated steroids, synthetic organic chemistry, molecular design, inhibition of NF-kB activation, mode-of-action
    2006.04.
  • Development of metabolically stable glyco-conjugates (glycolipids)
    keyword : glyco-conjugates, glycolipids, molecular design, synthetic organic chemistry, evaluation of biological functions
    2005.04.
  • Development of new molecular tools for chemical biology research on natural products or glyco-conjugates
    keyword : molecular design, synthetic organic chemistry, chemical biology
    2010.04.
  • Development of novel bioactive molecules based on natural products
    keyword : natural products, molecular design, synthetic organic chemistry, biochemical or biological evaluation
    2002.04.
Academic Activities
Reports
1. Go Hirai, Mimicking/Extracting Structure and Functions of Natural Products: Synthetic Approaches that Address Unexplored Needs in Chemical Biology, The Chemical Record (Personal Account).
2. Go Hirai, Mikiko Sodeoka, Focused Library with a Core Structure Extracted from Natural Products and Modified: Application to Phosphatase Inhibitors and Several Biochemical Findings, Acc. Chem. Res..
3. Go Hirai, Eisuke Ota, Motonari Sakai, Shigeru Nishiyama, Mikiko Sodeoka, C-Sialosides: Synthesis and Biological Activities(C-シアロシド結合を有する糖鎖アナログ:その合成と利用価値), Trends in glycoscience and glycotechnology (Minireview).
Papers
1. Yu Mikame, Kazuko Yoshida, Daisuke Hashizume, Go Hirai, Kazuo Nagasawa, Hiroyuki Osada, Mikiko Sodeoka, Synthesis of All Stereoisomers of RK460 and Evaluation of Their Activity and Selectivity as Abscisic Acid Receptor Antagonists, Chemistry - A European Journal, 10.1002/chem.201806056, 25, 14, 3496-3500, 2019.03, The PYR/PYL/RCAR protein families have recently emerged as receptors of the phytohormone abscisic acid (ABA, 1), which regulates plant responses to environmental stress. These families have multiple members with different physiological actions, and so selective agonists or antagonists are needed both as tools to elucidate functional differences and as lead compounds for agrochemicals. We previously identified RK460 (rac-3 a) as a PYR1-selective antagonist, and showed that it possesses five stereocenters on a 6,5-cis-bicyclo skeleton. Here, we synthesized all the stereoisomers of RK460 and evaluated their activity towards a panel of receptors. Relative stereochemistry as well as absolute stereochemistry was important for selective action..
2. Eisuke Ota, Kazuteru Usui, Kana Oonuma, Hiroyuki Koshino, Shigeru Nishiyama, Go Hirai, Mikiko Sodeoka, Thienyl-Substituted α-Ketoamide
A Less Hydrophobic Reactive Group for Photo-Affinity Labeling, ACS Chemical Biology, 10.1021/acschembio.7b00988, 13, 4, 876-880, 2018.02, Photoaffinity labeling (PAL) is an important tool in chemical biology research, but application of α-ketoamides for PAL has been hampered by their photoinstability. Here, we show that 2-thienyl-substituted α-ketoamide is a superior photoreactive group for PAL. Studies with a series of synthetic mannose-conjugated α-ketoamides revealed that 2-thienyl substitution of α-ketoamide decreased the electrophilicity of the keto group and reduced the rate of photodegradation. Mannose-conjugated thienyl α-ketoamide showed greater concanavalin A labeling efficiency than other alkyl or phenyl-substituted α-ketoamides. In comparison with representative conventional photoreactive groups, 2-thienyl ketoamide showed reduced labeling of nontarget proteins, probably owing to its lower hydrophobicity..
3. Morita Masaki, Shuntaro Kojima, Megumi Ohkubo, Hiroyuki Koshino, Daisuke Hashizume, Go Hirai, Keiji Maruoka, Mikiko Sodeoka, Synthesis of the Right-Side Structure of Type B Physalins, ISRAEL JOURNAL OF CHEMISTRY, 10.1002/ijch.201600110, 57, 309-318, 2017.04.
4. Qianqian Wang, Yuta Kuramoto, Yozo Okazaki, Eisuke Ota, Masaki Morita, Go Hirai, Kazuki Saito, Mikiko Sodeoka, Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation, Tetrahedron Letters, 10.1016/j.tetlet.2017.06.034, 58, 30, 2915-2918, 2017.01, We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyldiacylglycerol (GlcADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected α-isomer of GlcADG as the major product..
5. Xiaoying Sun, Go Hirai, Masashi Ueki, Hiroshi Hirota, Qianqian Wang, Yayoi Hongo, Takemichi Nakamura, Yuki Hitora, Hidekazu Takahashi, Mikiko Sodeoka, Hiroyuki Osada, Makiko Hamamoto, Minoru Yoshida, Yoko Yashiroda, Identification of novel secreted fatty acids that regulate nitrogen catabolite repression in fission yeast, Scientific Reports, 10.1038/srep20856, 6, 20856, 2016.02.
6. Eisuke Ota, Yu Mikame, Go Hirai, Shigeru Nishiyama, Mikiko Sodeoka, Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C–H Bond Activation, SYNLETT, 10.1055/s-0035-1561098, 27, 1128-1132, 2016.01.
7. Eisuke Ota, Yu Mikame, Go Hirai, Hiroyuki Koshino, Shigeru Nishiyama, Mikiko Sodeoka, Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation, Tetrahedron Lett., 10.1016/j.tetlet.2015.09.038, 56, 5991-5994, 2015.09.
8. Masaaki Ozawa, Masaki Morita, Go Hirai, Satoru Tamura, Masao Kawai, Ayako Tsuchiya, Kana Oonuma, Keiji Maruoka, and Mikiko Sodeoka, Contribution of Cage-Shaped Structure of Physalins to Their Mode of Action in Inhibition of NF-kB Action, ACS Med. Chem. Lett. , 10.1021/ml400144e, 4, 730-735, 2013.06.
9. Ayako Tsuchiya, Miwako Asanuma, Go Hirai, Kana Oonuma, Muhammad Muddassar, Eri Nishizawa, Yusuke Koyama, Yuko Otani, Kam Y. J. Zhang, and Mikiko Sodeoka, CDC25A-inhibitory RE Derivatives Bind to Pocket Adjacent to the Catalytic Site, Mol. BioSyst., 10.1039/C3MB00003F, 9, 1026-1034, 2013.02.
10. Ayako Tsuchiya, Go Hirai, Yusuke Koyama, Kana Oonuma, Yuko Otani, Hiroyuki Osada, and Mikiko Sodeoka, Dual-specificity Protein Phosphatase CDC25A/B Inhibitor Identified from a Focused Library with Non-electrophilic Enamine Core Structure, ACS Med. Chem. Lett. , 10.1021/ml2002778, 3, 264-298, 2012.02.
11. Go Hirai, Ayako Tsuchiya, Yusuke Koyama, Yuko Otani, Kana Oonuma, Kosuke Dodo, Siro Simizu, Hiroyuki Osada, and Mikiko Sodeoka, Development of a Vaccinia H1-Related (VHR) Phosphatase Inhibitor with NonAcidic Phosphate-Mimicking Core Structure, ChemMedChem, 10.1002/cmdc.201100107, 6, 617-622, 2011.03.
12. Megumi Ohkubo, Go Hirai, Mikiko Sodeoka, Synthesis of the DFGH ring system of Type B Physalins: Highly Oxygenated, Cage-Shaped Molecules, Angew. Chem. Int. Ed., 10.1002/anie.200900634, 48, 3862-3866, 2009.04.
13. Isao Fukuda, Akihiro Ito, Go Hirai, Shinichi Nishimura, Hisashi Kawasaki, Hisato Saitoh, Ken-ichi Kimura, Mikiko Sodeoka, Minoru Yoshida, Ginkgolic Acid Inhibits Protein SUMOylation by Blocking Formation of the E1-SUMO Intermediate, Chemistry & Biology, 10.1016/j.chembiol.2009.01.009, 16, 133-140, 2009.02.
14. Toru Watanabe, Go Hirai, Marie Kato, Daisuke Hashizume, Taeko Miyagi, and Mikiko Sodeoka, Synthesis of CH2-Linked α(2,3)Sialylgalactose Analogue: On the Stereoselectivity of the Key Ireland-Claisen Rearrangement, Org. Lett., 10.1021/ol801519j, 10, 4167-4170, 2008.09.
15. Go Hirai, Toru Watanabe, Kazunori Yamaguchi, Taeko Miyagi, and Mikiko Sodeoka, Stereocontrolled and Convergent Entry to CF2-Sialosides: Synthesis of CF2-Linked Ganglioside GM4, J. Am. Chem. Soc., 10.1021/ja075738w, 129, 15420-15421, 2007.11.
16. Masaki Morita, Go Hirai, Meguni Ohkubo Hiroyuki koshino, Daisuke Hashizume, Keiji Maruoka, and Mikiko Sodeoka, Kinetically Controlled One-Pot Formation of DEFGH-Rings of Type B Physalins through Domino-Type Transformations, Org, Lett., 14, 3434-3437.
Presentations
1. 平井 剛, Thienyl-Substituted α-Ketoamide: a Less Hydrophobic Photoreactive Group, The Third A3 Roundtable Meeting on Chemical Probe Research Hub, 2018.11.
2. Go Hirai, Synthesis of Natural Product Compartments for Finding Their Functions, The 3rd HU-TMU-KU Joint Symposium for Pharmaceutical Sciences, 2017.09.
3. Go Hirai, Synthesis of Monomers for Spectomycin B1, A Middle Size SUMOylation Inhibitor Molecule, 7th CCS/CSJ Young Chemist Forum, 2017.03.
4. Go Hirai, Synthesis of Monomers for Spectomycin B1, A Middle Size SUMOylation Inhibitor Molecule, 7th CCS/CSJ Young Chemist Forum(第7回日中若手化学者フォーラム), 2017.03.
Awards
  • Synthesis and Biological Evaluation of DEFGH-ring System of Physalins
Educational
Educational Activities
Synthetic Organic Chemistry and Bioorganic Chemistry for undergraduate or graduate students