Development of a novel type of carbohydrate probes

• Project/Area Number: 15K12760
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Chemical biology
• Research Institution: Kyushu University (2016-2017); Institute of Physical and Chemical Research (2015)
• Principal Investigator: Hirai Go 九州大学, 薬学研究院, 教授 (50359551)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000); Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
• Keywords: 複合糖質 / シアリダーゼ / 酵素反応 / 分子プローブ / シアル酸 / 代謝 / 有機合成 / プローブ / 有機化学 / 糖鎖 / 生体分子

Outline of Final Research Achievements

Carbohydrates (glycoconjugates) have important functions. Degradation of carbohydrates that play a role of "turning off" functions of original carbohydrates, is also important process in cells. However, it is not possible to monitor when or which enzymes degradate a specific glycoconjugate in cells. This time, a new molecular tool that can do this was successfully developed with our own idea.

Research Products

• [Journal Article] Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling (2018)
  • Author(s): Ota Eisuke、Usui Kazuteru、Oonuma Kana、Koshino Hiroyuki、Nishiyama Shigeru、Hirai Go、Sodeoka Mikiko
  • Journal Title: ACS Chemical Biology Volume: 13 Issue: 4 Pages: 876-880
  • DOI: 10.1021/acschembio.7b00988
  • Peer Reviewed
• [Journal Article] Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation (2017)
  • Author(s): Wang Qianqian、Kuramoto Yuta、Okazaki Yozo、Ota Eisuke、Morita Masaki、Hirai Go、Saito Kazuki、Sodeoka Mikiko
  • Journal Title: Tetrahedron Letters Volume: 58 Issue: 30 Pages: 2915-2918
  • DOI: 10.1016/j.tetlet.2017.06.034
  • Peer Reviewed
• [Journal Article] Synthesis of the Right-Side Structure of Type B Physalins (2017)
  • Author(s): Morita Masaki、Kojima Shuntaro、Ohkubo Megumi、Koshino Hiroyuki、Hashizume Daisuke、Hirai Go、Maruoka Keiji、Sodeoka Mikiko
  • Journal Title: Israel Journal of Chemistry Volume: 57 Issue: 3-4 Pages: 309-318
  • DOI: 10.1002/ijch.201600110
  • Peer Reviewed / Open Access
• [Journal Article] Photochemical and Additive-free Coupling Reaction of α-Cumyl α-Ketoesters via Intermolecular C-H Bond Activation (2016)
  • Author(s): Eisuke Ota, Yu Mikame, Go Hirai, Shigeru Nishiyama, Mikiko Sodeoka
  • Journal Title: Synlett Volume: 27 Issue: 07 Pages: 1128-1132
  • DOI: 10.1055/s-0035-1561098
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A new carbamidemethyl-linked lanthanide chelating tag for PCS NMR spectroscopy of proteins in living HeLa cells. (2016)
  • Author(s): Yuya Hikone, Go Hirai, Masaki Mishima, Kohsuke Inomata, Teppei Ikeya, Souichiro Arai, Masahiro Shirakawa, Mikiko Sodeoka, and Yutaka Ito
  • Journal Title: Journal of Biomolecular NMR Volume: 66 Issue: 2 Pages: 99-110
  • DOI: 10.1007/s10858-016-0059-4
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Rational Design and Synthesis of [5]Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions (2016)
  • Author(s): Kosuke Yamamoto, Takashi Shimizu, Kazunobu Igawa, Katsuhiko Tomooka, Go Hirai, Hiroshi Suemune, and Kazuteru Usui
  • Journal Title: Scientific Reports Volume: 6 Issue: 1 Pages: 36211-36211
  • DOI: 10.1038/srep36211
  • Peer Reviewed / Open Access
• [Journal Article] Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation (2016)
  • Author(s): Takayuki Ohyoshi, Yuki Tamura, Ichiro Hayakawa, Go Hirai, Yamato Miyazawa, Shota Funakubo, Mikiko Sodeoka, and Hideo Kigoshi
  • Journal Title: Org. Biomol. Chem. Volume: 14 Issue: 48 Pages: 11426-11437
  • DOI: 10.1039/c6ob02268e
  • NAID: 120007135231
  • Peer Reviewed
• [Journal Article] Comparative Characterization of the Leaf Tissue of Physalis alkekengi and Physalis peruviana Using RNA-seq and Metabolite Profiling (2016)
  • Author(s): Atsushi Fukushima, Michimi Nakamura, Hideyuki Suzuki, Mami Yamazaki, Eva Knoch, Tetsuya Mori, Naoyuki Umemoto, Masaki Morita, Go Hirai, Mikiko Sodeoka, and Kazuki Saito
  • Journal Title: Frontiers in Plant Science Volume: 7 Pages: 1883-1883
  • DOI: 10.3389/fpls.2016.01883
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Identification of novel secreted fatty acids that regulate nitrogen catabolite repression in fission yeast. (2016)
  • Author(s): Sun X, Hirai G, Ueki M, Hirota H, Wang Q, Hongo Y, Nakamura T, Hitora Y, Takahashi H, Sodeoka M, Osada H, Hamamoto M, Yoshida M, Yashiroda Y.
  • Journal Title: Scientific Reports Volume: 6 Issue: 1 Pages: 20856-20856
  • DOI: 10.1038/srep20856
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Reactions of Carbonyl Compounds with Phosphorus Ylide Generated from Tribromofluoromethane and Tris(dimethylamino)phosphine (2015)
  • Author(s): Go Hirai, Eri Nishizawa, Daiki Kakumoto, Masaki Morita, Mitsuaki Okada, Daisuke Hashizume, Sayoko Nagashima, Mikiko Sodeoka
  • Journal Title: Chem. Lett Volume: 44 Issue: 10 Pages: 1389-1391
  • DOI: 10.1246/cl.150523
  • NAID: 130005101456
  • Peer Reviewed
• [Journal Article] Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation (2015)
  • Author(s): Eisuke Ota, Yu Mikame, Go Hirai, Hiroyuki Koshino, Shigeru Nishiyama, Mikiko Sodeoka
  • Journal Title: Tetrahedron Lett. Volume: 56 Issue: 44 Pages: 5991-5994
  • DOI: 10.1016/j.tetlet.2015.09.038
  • Peer Reviewed
• [Journal Article] Focused Library with a Core Structure Extracted from Natural Products and Modified: Application to Phosphatase Inhibitors and Several Biochemical Findings (2015)
  • Author(s): Go Hirai and Mikiko Sodeoka
  • Journal Title: Acc. Chem. Res. Volume: 48 Issue: 5 Pages: 1464-1473
  • DOI: 10.1021/acs.accounts.5b00048
  • Peer Reviewed
• [Presentation] 代謝に着目した中分子糖鎖分子の設計と機能 (2017)
  • Author(s): 平井剛
  • Organizer: 日本薬学会第137年会一般シンポジウム「中分子創薬研究のフロンティア－反応集積化が導く中分子戦略：高次生物機能分子の創製－
  • Place of Presentation: 仙台国際センター
  • Year and Date: 2017-03-27
  • Invited
• [Presentation] Development of the Disaccharide-Type Activity-Based Probe for Sialidase (2017)
  • Author(s): 深澤亮、大沼可奈、加藤麻理依、平井剛、袖岡幹子
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2017-03-17
• [Presentation] 人工糖鎖を備えて未来の疾患と戦う (2017)
  • Author(s): 平井剛
  • Organizer: 第7回CSJ化学フェスタ2017「10年後にはどんな分子ができる？有機合成化学者の「革命分子」への挑戦」 (2017.10.18)
  • Invited
• [Presentation] 非天然型複合糖質を創る (2017)
  • Author(s): 平井剛
  • Organizer: 糸状菌分子生物学研究会 第5回若手の会 WS in SAGA
  • Invited
• [Presentation] α-ケトアミドを基盤とする新しい光親和性標識実験用プローブの開発 (2017)
  • Author(s): 平井剛、太田英介、臼井一晃、大沼可奈、袖岡幹子
  • Organizer: 日本ケミカルバイオロジー学会 第12回年会
• [Presentation] シアリダーゼに対する新規activity-based probeの開発 (2017)
  • Author(s): 平井剛、深澤亮、大沼可奈、森田昌樹、加藤麻理依、袖岡幹子
  • Organizer: 第35回メディシナルケミストリーシンポジウム
• [Presentation] 高機能性複合糖質の創製 (2016)
  • Author(s): 平井剛
  • Organizer: 日本化学会中国四国支部地区化学講演会「「有機化学者による生命科学へのアプローチ」
  • Place of Presentation: 岡山大学理学部
  • Year and Date: 2016-12-10
  • Invited
• [Presentation] シアリダーゼの機能解析を志向した3位修飾型シアル酸誘導体の合成と活性評価 (2016)
  • Author(s): 深澤亮、平井剛、加藤麻理依、大沼可奈、越野広雪、袖岡幹子
  • Organizer: 第58回天然有機化合物討論会
  • Place of Presentation: 東北大萩ホール
  • Year and Date: 2016-09-15
• [Presentation] 生物活性分子創製研究と有機合成研究の融合 (2016)
  • Author(s): 平井剛
  • Organizer: 熊本大学理学部化学特別講義C講演会
  • Place of Presentation: 熊本大学理学部
  • Year and Date: 2016-05-24
  • Invited
• [Presentation] ケミカルバイオロジーに役立つものづくりを目指して (2016)
  • Author(s): 平井剛
  • Organizer: 特別企画: 有機合成化学を起点とするものづくり戦略 (日本化学会第96回春季年会)
  • Place of Presentation: 同志社大学京田辺キャンパス（京都府京田辺市）
  • Year and Date: 2016-03-24
  • Invited
• [Presentation] Fluorine containing C-linked gangliosides GM3 analogs: Synthesis, conformational analysis, and biological activities (2015)
  • Author(s): Go Hirai, Marie Kato, Kana Oonuma, Eri Nishizawa, Hiroyuki Koshino, Mikiko Sodeoka
  • Organizer: Molecular Function of Natural Products: Advances towards Chemical Biology, PacifiChem 2015
  • Place of Presentation: Honolulu (USA)
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Spectomycin A1全異性体の合成とSUMO化阻害活性 (2015)
  • Author(s): 平井剛、野村勇作、Frederic Thuaud、前田里子、伊藤昭博、吉田稔、市川聡、松田彰、袖岡幹子
  • Organizer: 日本ケミカルバイオロジー学会 第10回年会
  • Place of Presentation: 東北大学川内萩ホール（宮城県仙台市）
  • Year and Date: 2015-06-10
• [Book] 天然有機化合物の全合成 (2018)
  • Author(s): 日本化学会
  • Total Pages: 208
  • Publisher: 化学同人
  • ISBN: 9784759813876
• [Remarks] 光親和性標識法の新たな分子ツールの開発－疎水性が低くコンパクトな光 反応性基－
  • URL: https://www.kyushu-u.ac.jp/f/32524/18_02_22_3.pdf
• [Patent(Industrial Property Rights)] シアル酸誘導体 (2016)
  • Inventor(s): 平井剛、深澤亮、袖岡幹子
  • Industrial Property Rights Holder: 平井剛、深澤亮、袖岡幹子
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2016-147705
  • Filing Date: 2016-07-27