Rapid analysis of photoaffinity label components by probes with multiple tag

• Project/Area Number: 17K01940
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Biomolecular chemistry
• Research Institution: Hokkaido University
• Principal Investigator: Hashimoto Makoto 北海道大学, 農学研究院, 准教授 (90292094)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Project Status: Completed (Fiscal Year 2019)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2018: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2017: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: 光アフィニティーラベル / 機能解析 / 生理活性物質 / 生理活性発現 / 構造活性相関 / 機能分子解析 / ジアジリン / 機能解析 /

Outline of Final Research Achievements

The detection tags are essential for photoaffinity labeling, which is one of the most reliable methods to elucidate of ligand biological activities. Post-derivatization for the ligand structure of photoaffinity probes are one of the fashion to detect photo labeled components. But isolations of photo labeled components are not easy due to there is no effect methods to isolate the small amounts of labeled components. We found that alpha-aminoketone structure was utilized to cleave specifically by photo-irradiation with different wavelength from photoaffinity labeling. Irradiations with different wavelength is easy to handle to elucidate the ligand-biomolecules relationship.

Academic Significance and Societal Importance of the Research Achievements

光アフィニティーラベルは「合成した生理活性物質誘導体は光照射まで標的生体高分子に対し元となる生理活性物質とほぼ同様な挙動を示し、通常の生化学的手法により取り扱いができる」事が利点であり幅広く利用されている。その一方「生理活性物質骨格に光反応性基ならびにラベル後解析の目印となるタグを導入する必要があり、生体高分子との親和性に影響を及ぼす可能性がある」事が問題として挙げられる。申請者をはじめ国内外の多くの研究者が、生理活性物質の誘導体化時の構造変化を最小限にとどめ、光照射後に解析用タグを有機化学的手法により導入する方法の確立に成功し、生理活性物質の機能解析の効率化に成功した。

Research Products

• [Journal Article] Hydrogen-Deuterium Exchange of Histidine and Histamine with Deuterated Trifluoromethanesulfonic Acid (2020)
  • Author(s): Hashimoto Makoto、Puteri Tachrim Zetryana、Kurokawa Natsumi、Tokoro Yurika
  • Journal Title: HETEROCYCLES Volume: 101 Issue: 1 Pages: 357-357
  • DOI: 10.3987/com-19-s(f)28
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of chiral N-trifluoroacetyl-methionine derivatives and applying them as acyl donors for Friedel-Crafts acylation (2019)
  • Author(s): Kurokawa Natsumi、Tokoro Yurika、Tachrim Zetryana Puteri、Wakasa Haruna、Sakihama Yasuko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Arkivoc Volume: 2019 Issue: 5 Pages: 42-49
  • DOI: 10.24820/ark.5550190.p010.815
  • NAID: 120006633290
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Deuterated CycloDOPA with Hydrogen/Deuterium Exchange (2019)
  • Author(s): Hashimoto Makoto、Puteri Tachrim Zetryana、Nakagawa Shiori、Nakamura Tadashi、Ohashi Fumina、Kurokawa Natsumi、Wakasa Haruna、Tokoro Yurika、Sakihama Yasuko、Hashidoko Yasuyuki、Suzuki Takeyuki
  • Journal Title: HETEROCYCLES Volume: 99 Issue: 1 Pages: 404-404
  • DOI: 10.3987/com-18-s(f)33
  • Peer Reviewed / Open Access
• [Journal Article] Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor (2019)
  • Author(s): Nakagita T, Ishida A, Matsuya T, Kobayashi T, Narukawa M, Hirokawa T, Hashimoto M, and Misaka T
  • Journal Title: PLoS ONE Volume: 14 Issue: 3 Pages: e0213552-e0213552
  • DOI: 10.1371/journal.pone.0213552
  • NAID: 120007133042
  • Peer Reviewed / Open Access
• [Journal Article] TFA-Protected α-Amino Acid N-Hydroxysuccinimide Ester: Application for Inter- and Intramolecular Acylation (2018)
  • Author(s): Hashimoto Makoto、Puteri Tachrim Zetryana、Oida Kazuhiro、Ohashi Fumina、Wakasa Haruna、Ikemoto Haruka、Kurokawa Natsumi、Sakihama Yasuko、Hashidoko Yasuyuki、Suzuki Takeyuki
  • Journal Title: HETEROCYCLES Volume: 97 Issue: 2 Pages: 877-877
  • DOI: 10.3987/com-18-s(t)65
  • Peer Reviewed
• [Journal Article] Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: Synthesis of 6,6',6''-trihalogenated 1-kestose derivatives (2018)
  • Author(s): Tachrim Zetryana Puteri、Nakamura Tadashi、Sakihama Yasuko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Arkivoc Volume: 2018 Issue: 7 Pages: 341-348
  • DOI: 10.24820/ark.5550190.p010.706
  • NAID: 120006630544
  • Peer Reviewed
• [Journal Article] Optimization of sucrose 1?-position modification with 3-(trifluoromethyl)diazirinyl benzylbromide derivatives for photoaffinity labeling (2018)
  • Author(s): Wang Lei、Tachrim Zetryana Puteri、Kurokawa Natsumi、Ohashi Fumina、Wakasa Haruna、Sakihama Yasuko、Hashidoko Yasuyuki、Suzuki Takeyuki、Hashimoto Makoto
  • Journal Title: Arkivoc Volume: 2018 Issue: 7 Pages: 58-65
  • DOI: 10.24820/ark.5550190.p010.668
  • NAID: 120006630543
• [Journal Article] pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives (2018)
  • Author(s): Nakagawa Shiori、Tachrim Zetryana、Kurokawa Natsumi、Ohashi Fumina、Sakihama Yasuko、Suzuki Takeyuki、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Molecules Volume: 23 Issue: 8 Pages: 1943-1943
  • DOI: 10.3390/molecules23081943
  • NAID: 120006534469
• [Journal Article] Dehydrogenation of the NH?NH Bond Triggered by Potassiumtert-Butoxide in Liquid Ammonia (2017)
  • Author(s): Wang Lei、Ishida Akiko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Angew. Chem. Int. Ed. Volume: 56 Issue: 3 Pages: 870-873
  • DOI: 10.1002/anie.201610371
  • NAID: 120006377487
  • Peer Reviewed
• [Journal Article] Comprehensive Synthesis of Photoreactive Phenylthiourea Derivatives for the Photoaffinity Labeling (2017)
  • Author(s): Ishida Akiko、Wang Lei、Tachrim Zetryana Puteri、Suzuki Takeyuki、Sakihama Yasuko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: ChemistrySelect Volume: 2 Issue: 1 Pages: 160-164
  • DOI: 10.1002/slct.201601675
  • NAID: 120006377484
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Photophore and Fluorophore Modified O-Benzylserine Derivatives (2017)
  • Author(s): Makoto Hashimoto, Takuma Yoshida, Zetryana Puteri Tachrim, YasukoSakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Yuichi Kanaoka
  • Journal Title: Heterocycles Volume: 95 Issue: 1 Pages: 462-473
  • DOI: 10.3987/com-16-s(s)37
  • Peer Reviewed
• [Journal Article] Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling (2017)
  • Author(s): Wang Lei、Tachrim Zetryana Puteri、Kurokawa Natsumi、Ohashi Fumina、Sakihama Yasuko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Molecules Volume: 22 Issue: 8 Pages: 1389-1389
  • DOI: 10.3390/molecules22081389
  • NAID: 120006352224
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel?Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester (2017)
  • Author(s): Tachrim Zetryana、Oida Kazuhiro、Ikemoto Haruka、Ohashi Fumina、Kurokawa Natsumi、Hayashi Kento、Shikanai Mami、Sakihama Yasuko、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Molecules Volume: 22 Issue: 10 Pages: 1748-1748
  • DOI: 10.3390/molecules22101748
  • NAID: 120006373741
  • Peer Reviewed / Open Access
• [Journal Article] Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions (2017)
  • Author(s): Tachrim Zetryana、Wang Lei、Murai Yuta、Yoshida Takuma、Kurokawa Natsumi、Ohashi Fumina、Hashidoko Yasuyuki、Hashimoto Makoto
  • Journal Title: Catalysts Volume: 7 Issue: 2 Pages: 40-40
  • DOI: 10.3390/catal7020040
  • Peer Reviewed / Open Access
• [Presentation] 塩化アルミニウムによるメチオニン誘導体の分子内環化反応の検討 (2019)
  • Author(s): 所 百合花、黒川 菜摘、橋床 泰之、橋本 誠
  • Organizer: 日本農芸化学会２０１９年度大会
• [Presentation] Phenylalkanoic acidの分子内環化反応の検討 (2019)
  • Author(s): 所 百合花，橋本 誠
  • Organizer: 2019年度 日本農芸化学会 北海道支部第2回講演会
• [Presentation] α-アミノ酸N-ヒドロキシスクシンイミドエステルを利用した Friedel-Crafts反応 (2019)
  • Author(s): Zetryana Puteri Tachrim、黒川菜摘、所百合花、 橋本 誠
  • Organizer: 第115回有機合成シンポジウム2019年【春】
• [Presentation] Stereo-controlable α-amino aryl ketone formation: α-Amino N-hydroxysuccinimide ester derivatives as acyl donor for Friedel-Crafts acylation (2018)
  • Author(s): Z. P. Tachrim, Y. Hashidoko, M. Hashimoto
  • Organizer: 日本農芸化学会２０１８年度大会
• [Presentation] 芳香族アミノ酸への光反応性基導入法の検討 (2018)
  • Author(s): M. HASHIMOTO, L. Wang, Y. Hashidoko
  • Organizer: 日本農芸化学会２０１８年度大会
• [Presentation] cycloDOPA誘導体のpH安定性とその抗酸化能 (2018)
  • Author(s): 中川詩織、Zetryana Puteri Tachrim、崎浜靖子、橋床泰之、橋本 誠
  • Organizer: 日本農芸化学会東北・北海道合同支部大会
• [Presentation] 光学活性N-トリフルオロアセチルフェニルグリシンスクシンイミドエステルの合成とペプチド合成への応用 (2018)
  • Author(s): 大橋史奈、橋床泰之、橋本 誠
  • Organizer: 日本農芸化学会東北・北海道合同支部大会
• [Presentation] Friedel-Crafts反応によるα-アミノ芳香族ケトンの合成とその光分解反応の検討 (2017)
  • Author(s): 種田 和洋，橋床 泰之，橋本 誠
  • Organizer: 平成２９年度 公益社団法人 日本農芸化学会 北海道支部第２回講演会
• [Presentation] メチオニンを利用したFriedel-Craftsアシル化反応の検討 (2017)
  • Author(s): 黒川菜摘, 橋床泰之, 橋本 誠
  • Organizer: 新アミノ酸分析研究会第7回学術講演会
• [Presentation] N-アシル-フェニルグリシン-スクシンイミドエステルの立体選択的合成 (2017)
  • Author(s): 大橋史奈, 橋床泰之, 橋本 誠
  • Organizer: 平成２９年度 日本農芸化学会 北海道支部第１回講演会
• [Presentation] スクロース１級水酸基のAppel試薬によるハロゲン化反応の検討 (2017)
  • Author(s): ゼトリアナ プテリ タクリム、武藤美帆、中村 正、 橋床 泰之、 橋本 誠
  • Organizer: 第36回 日本糖質学会年会
• [Book] Photoaffinity Labeling for Structural Probing Within Protein (2017)
  • Author(s): Hatanaka Yasumaru., Hashimoto Makoto 編集
  • Total Pages: 265
  • Publisher: Springer
  • ISBN: 9784431565680
• [Remarks] 北大院農 生態化学生物学 化学生物学G ブログ
  • URL: http://lmec2.blog.fc2.com/