Liposome Membrane as a Platform for the l -Pro-Catalyzed Michael Addition of trans-β-Nitrostyrene and Acetone

Masanori Hirose, Takaaki Ishigami, Keishi Suga, Hiroshi Umakoshi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Herein, we show that the l-proline (l-Pro)-catalyzed Michael addition of trans-β-nitrostyrene and acetone can proceed in "water" using liposome membranes and that the membrane fluidity and polarity are major controlling factors for this reaction. The highest conversion and rate constant of the reaction within the liposomes was achieved with the 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC)/1,2-dipalmitoyl-3-trimethylammoniumpropane (DPTAP) system. The catalytic activity of l-Pro in the liposome suspension was found to be comparable to that in a DMSO system. The reaction rate constant was found to be controlled by both the phase state of the liposome membrane and the surface charge on the membrane. Greater enantioselectivity was achieved in the presence of the liposomes than in DMSO solution, with corresponding enantiomeric excess values of 97.6% for the DOPC/DPTAP liposome system and 10% in DMSO. The hydrophobic region of the liposome membrane, which is a relatively stable self-organizing system, can serve as an effective "platform" for molecular recognition and selective conversion in aqueous media.

Original languageEnglish
Pages (from-to)12968-12974
Number of pages7
JournalLangmuir
Volume31
Issue number47
DOIs
Publication statusPublished - 2015 Nov 8
Externally publishedYes

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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