Pseudo-Interphase of Liposome Promotes 1,3-Dipolar Cycloaddition Reaction of Benzonitrile Oxide and N -Ethylmaleimide in Aqueous Solution

Fumihiko Iwasaki, Keishi Suga, Hiroshi Umakoshi

研究成果: Article査読

18 被引用数 (Scopus)

抄録

The hydrophobic interior of a liposome membrane was used as a platform for the organic synthesis of hydrophobic compounds in water. The 1,3-dipolar cycloaddition of benzonitrile oxide (BNO) and N-ethylmaleimide (EMI) in liposome suspensions was carried out, and an increase in the reaction rate constant was observed depending on the liposome characteristics. While the reaction rate constant in 1,4-dioxane was 1.5 times higher than that in water, the reaction rate constant in an aqueous solution of cationic 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) liposome was 3 times higher than in water. The amount of substrate, BNO, accumulated in the DOTAP liposome was higher than that in 1,2-dipalmitoyl-3-trimethylammonium-propane (DPTAP), indicating that BNO prefers to be distributed in the liposome membrane in the liquid-disordered phase. The membrane polarity, GP340, as monitored by Laurdan, varied with the presence of BNO, while EMI slightly affected the membrane properties of the liposomes. These results suggest that the pseudo-interphase afforded by the liposome membrane can promote the 1,3-dipolar cycloaddition between BNO and EMI in water.

本文言語English
ページ(範囲)9772-9779
ページ数8
ジャーナルJournal of Physical Chemistry B
119
30
DOI
出版ステータスPublished - 2015 7 30
外部発表はい

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 表面、皮膜および薄膜
  • 材料化学

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