Applications of solid phase for photoaffinity labeling

• Project/Area Number: 21510219
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Hokkaido University
• Principal Investigator: HASHIMOTO Makoto 北海道大学, 大学院・農学研究院, 准教授 (90292094)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 光アフィニティーラベル / ジアジリン / アビジン-ビオチン / 固層担体 / 有機化学反応 / アビジンービオチン / 有機反応

Research Abstract

Novel functional analysis of pinteractions between biomolecules and bioactive compounds with photoreactive trifluoromethylphenyldiazirine containing biotin derivative and immobilized monomeric avidin were examined. New findings are listed below.
(1) Synthesis of photoreactive biotinylated compounds
(2) Photoaffinity labeling with photoreactive biotinylated ligands on immobilized monomeric avidin.
(3) Novel synthesis of biotinylated compounds, which was prepared by Friedel-Crafts reactions.

Research Products

• [Journal Article] Chemo-enzymatic synthesis of 1'-photoreactive sucrose derivatives viaether linkage (2012)
  • Author(s): Yuka Tsunekawa, Katsuyoshi Masuda, Miho Muto, Yasuyuki Muto, Yuta Murai, Yasuyuki Hashidoko, Yoshitake Orikasa, Yuji Oda, Yasumaru Hatanaka, Makoto Hashimoto
  • Journal Title: Heterocycles Volume: 84 Pages: 283-290
  • NAID: 120005183186
  • Peer Reviewed
• [Journal Article] Chemo-enzymatic synthesis of 1'-photoreactive sucrose derivatives via ether linkage (2012)
  • Author(s): Yuka Tsunekawa, Katsuyoshi Masuda, Miho Muto, Yasuyuki Muto, Yuta Murai, Yasuyuki Hashidoko, Yoshitake Orikasa, Yuji Oda, Yasumaru Hatanaka, Makoto Hashimoto
  • Journal Title: Heterocycles Volume: 84 Issue: 1 Pages: 283-290
  • DOI: 10.3987/com-11-s(p)19
  • NAID: 120005183186
  • Peer Reviewed
• [Journal Article] Novel synthesis of optically active bishomotyrosine derivatives using the Friedel-Crafts reaction in triflic acid (2011)
  • Author(s): Yuta Murai, Yasuyuki Hashidoko, Makoto Hashimoto
  • Journal Title: Biosci. Biotechnol. Biochem. Volume: 75 Pages: 352-354
  • NAID: 10027898056
  • Peer Reviewed
• [Journal Article] Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid : Effective synthesis of optically active homotyrosines (2011)
  • Author(s): Ryo Murashige, Yuka Hayashi, Syo Ohmori, Ayuko Torii, Yoko Aizu, Yasuyuki Muto, Yuta Murai, Yuji Oda, Makoto Hashimoto
  • Journal Title: Tetrahedron Volume: 67 Pages: 641-649
  • NAID: 120002741676
  • Peer Reviewed
• [Journal Article] Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluorometh anesulfonic acid : Effective synthesis of optically active homotyrosines (2011)
  • Author(s): Ryo Murashige, Yuka Hayashi, Syo Ohmori, Ayuko Torii, Yoko Aizu, Yasuyuki Muto, Yuta Murai, Yuji Oda, Makoto Hashimoto
  • Journal Title: Tetrahedron Volume: 67 Issue: 3 Pages: 641-649
  • DOI: 10.1016/j.tet.2010.11.047
  • NAID: 120002741676
  • Peer Reviewed
• [Journal Article] Novel Synthesis of Optically Active Bishomotyrosine Derivatives Using the Friedel-Crafts Reaction in Triflic Acid (2011)
  • Author(s): Yuta Murai, Yasuyuki Hashidoko, Makoto Hashimoto
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 75 Issue: 2 Pages: 352-354
  • DOI: 10.1271/bbb.100595
  • NAID: 10027898056
  • ISSN: 0916-8451, 1347-6947
  • Peer Reviewed
• [Journal Article] Simple deuterium introduction at α-position of carbonyl in diazirinyl derivatives for photoaffinity labeling (2010)
  • Author(s): Yuta Murai, Miho Takahashi, Yasuyuki Muto, Yasumaru Hatanaka, Makoto Hashimoto
  • Journal Title: Heterocycles Volume: 82 Pages: 909-915
  • NAID: 120002834724
  • Peer Reviewed
• [Journal Article] Synthesis and properties of diazirinylorgano-platinum compounds for manipulations of photoaffinity labeled components (2010)
  • Author(s): Makoto Hashimoto, Keitaro Furukawa, Takenori Tomohiro, Yasumaru Hatanaka
  • Journal Title: Chem. Pharm. Bull. Volume: 58 Pages: 405-407
  • NAID: 130000255923
  • Peer Reviewed
• [Journal Article] Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl D-phenylalanine derivatives (2010)
  • Author(s): Katsuyoshi Masuda, Ayako Koizumi, Takumi Misaka, Yasumaru Hatanaka, Keiko Abe, Takaharu Tanaka, Masaji Ishiguro, Makoto Hashimoto
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: 20 Pages: 1081-1083
  • NAID: 120001875431
  • Peer Reviewed
• [Journal Article] Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl D-phenylalanine derivatives (2010)
  • Author(s): K.Masuda, A.Koizumi, T.Misaka, Y.Hatanaka, K.Abe, T.Tanaka, M.Ishiguro, M.Hashimoto
  • Journal Title: Bioorg.Med.Chem.Lett. Volume: 20 Pages: 1081-1083
  • NAID: 120001875431
  • Peer Reviewed
• [Journal Article] Synthesis and properties of diazirinyl organo-platinum compounds for manipulations of photoaffinity labeled components (2010)
  • Author(s): M.Hashimoto, K.Furukawa, T.Tomohiro, Y.Hatanaka
  • Journal Title: Chem.Pharm.Bull. Volume: 58 Pages: 405-407
  • NAID: 130000255923
  • Peer Reviewed
• [Journal Article] Effective synthesis of opticaly active 3-phenyl-3-(3-trifluoromethyl) diazirinyl bishomophenylalanine derivatives (2009)
  • Author(s): Yuta Murai, Yasumaru Hatanaka, Yuichi Kanaoka, Makoto Hashimoto
  • Journal Title: Heterocycles Volume: 79 Pages: 359-364
  • Peer Reviewed
• [Journal Article] Effective synthesis of optically active trifluoromethyldiazirinyl homophenyl-alanineand aroylalanine derivatives with Friedel-Crafts reactions in triflic acid (2009)
  • Author(s): Ryo Murashige, Yuta Murai, Yasumaru Hatanaka, Makoto Hashimoto
  • Journal Title: Biosci. Biotechnol. Biochem. Volume: 73 Pages: 1377-1380
  • Peer Reviewed
• [Journal Article] Effective synthesis of opticaly active 3-phenyl-3-(3-trifluoromethyl) diazirinyl bishomophenylalanine derivatives (2009)
  • Author(s): Y.Murai, Y.Hatanaka, Y.Kanaoka, M.Hashimoto
  • Journal Title: Heterocycles 79 Pages: 359-364
  • Peer Reviewed
• [Journal Article] Effective synthesis of optically active trifluoromethyldiazirinyl homophenylalanine and aroylalanine derivatives with Friedel-Crafts reactions in triflic acid (2009)
  • Author(s): R.Murashige, Y.Murai, Y.Hatanaka, M.Hashimoto
  • Journal Title: Biosci.Biotechnol.Biochem. 73 Pages: 1377-1380
  • NAID: 10027542555
  • Peer Reviewed
• [Presentation] Triflic acidを用いたFriedel-Crafts反応によるビオチン新規誘導体化の検討 (2012)
  • Author(s): 武藤靖幸、橋床泰之、橋本誠
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都女子大学(京都市)
  • Year and Date: 2012-03-24
• [Presentation] Simple introduction of deuterium at α-position of carbonyl in diazirinyl compounds for photoaffinity labeling (2010)
  • Author(s): Y.Murai, Y.Hashidoko, Y.Hatanaka, M.Hashimoto
  • Organizer: 2010 International Chemical congress of pacific basin societies
  • Place of Presentation: Honolulu, Hawaii, USA.
  • Year and Date: 2010-12-17
• [Presentation] 味覚関連アミノ酸およびペプチド用光アフィニティーラベル試薬合成 (2010)
  • Author(s): 橋本誠、畑中保丸
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 岡山
• [Presentation] 機能性解析を指向した光アフィニティーラベル法の開発 (2009)
  • Author(s): 橋本誠
  • Organizer: 日本農芸化学会北海道支部支部奨励賞受賞講演
  • Place of Presentation: 札幌、北海道大学百年記念館
  • Year and Date: 2009-07-24
• [Presentation] 芳香族アミノ酸側鎖構造活性相関解析用光アフィニティーラベル試薬の立体選択的合成 (2009)
  • Author(s): 橋本誠、村重諒、村井勇太、畑中保丸
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] 機能性解析を指向した光アフィニティーラベル法の開発 (2009)
  • Author(s): 橋本誠
  • Organizer: 日本農芸化学会北海道支部奨励賞受賞講演
  • Place of Presentation: 札幌