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

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)9772-9779
Number of pages8
JournalJournal of Physical Chemistry B
Volume119
Issue number30
DOIs
Publication statusPublished - 2015 Jul 30
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

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