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Preparation of oligopeptides with lipophilic ionpairs and control of solubility in organic solvents

Research Project

Project/Area Number 26620091
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionHokkaido University

Principal Investigator

SADA KAZUKI  北海道大学, 理学(系)研究科(研究院), 教授 (80225911)

Co-Investigator(Kenkyū-buntansha) KOKADO KENTA  北海道大学, 大学院理学研究院, 助教 (40600226)
Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsイオン対 / オリゴペプチド / 生体機能利用 / 分子認識 / イオン解離 / 可溶化 / 超分子化学 / 親油性イオン対
Outline of Final Research Achievements

In this research project, we investigated incorporation of tetraalkylammonium tetraphenylborate as a lipophilic ionpair into some lipophilic oligopeptide chains and enhancement of solubility in less polar media by introducing the ionpair. FMOC solid-state synthesis provided oligopeptides with 5-13 amino acid with one or two acetylenic residues. Then, click reaction between these oligopeptides and azide-modified tetraalkylammonium tetraphenylborate gave the oligopeptides. ESI-mass spectrometry clearly indicated introduction of tetraphenylborate tetraalkylaamonium ionpair. They were soluble in 1,2-dicholroethane and solubility of the oligopeptides with this ionpair increased compared to that of the unmodified oligopeptides. Therefore, incorporation of the lipophilic ionpair should contribute to solubility due to electrostatic repulsion and osmotic pressure.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (5 results)

All 2016 2015

All Presentation (5 results) (of which Int'l Joint Research: 1 results)

  • [Presentation] 親油性電解質を有するオリゴペプチドの合成2016

    • Author(s)
      福島寛太・須永総玄・南部貴則・小門憲太・佐田和己
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] イオン対を疎水部とする両親媒性分子の分子集合体形成2016

    • Author(s)
      山田泰平・小門憲太・佐田和己
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Reverse amphiphiles having a lipophilic ion pair as the hydrophobic part2015

    • Author(s)
      Yamada, Taihei; Kokado,Kenta; Sada, Kazuki
    • Organizer
      Pacifichem2015
    • Place of Presentation
      ハワイコンベンションセンター(1801 Kalakaua Ave, Honolulu, USA)
    • Year and Date
      2015-12-12
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 非極性溶媒中での静電相互作用による両親媒性糖誘導体の分子集合体制御2015

    • Author(s)
      山田泰平・小門憲太・佐田和己
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市青葉区川内27-1)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] イオン対を疎水部とする両親媒性分子の合成と分子集合体形成2015

    • Author(s)
      山田泰平・小門憲太・佐田和己
    • Organizer
      第66回コロイドおよび界面化学討論会
    • Place of Presentation
      鹿児島大学郡元キャンパス(鹿児島県鹿児島市郡元1丁目21-24)
    • Year and Date
      2015-09-10
    • Related Report
      2015 Annual Research Report

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Published: 2014-04-04   Modified: 2017-05-10  

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