Application of liposome membrane as the reaction field: A case study using the Horner–Wadsworth–Emmons reaction

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Abstract

The properties of the liposome membrane as a reaction field were investigated by focusing on the Horner–Wadsworth–Emmons reaction as a case study. Use of the liposomes existing in the gel phase resulted in the enhanced activity of the substrates and furnished the products with same E/Z stereoselectivity as in the liposome-free system. The membrane environment in the gel phase most likely assisted the formation of adducts that induced selective generation of the E-isomer. The possible role of liposomes is to assist the proton removal from the reactant, rather than providing the basic interfacial environment.

Original languageEnglish
JournalJournal of Bioscience and Bioengineering
DOIs
Publication statusPublished - Jan 1 2019

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Liposomes
Membranes
Gels
Stereoselectivity
Isomers
Protons
Substrates

Keywords

  • Horner–Wadsworth–Emmons reaction
  • Liposome
  • Phospholipid
  • Reaction field
  • Stereochemistry

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

Cite this

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title = "Application of liposome membrane as the reaction field: A case study using the Horner–Wadsworth–Emmons reaction",
abstract = "The properties of the liposome membrane as a reaction field were investigated by focusing on the Horner–Wadsworth–Emmons reaction as a case study. Use of the liposomes existing in the gel phase resulted in the enhanced activity of the substrates and furnished the products with same E/Z stereoselectivity as in the liposome-free system. The membrane environment in the gel phase most likely assisted the formation of adducts that induced selective generation of the E-isomer. The possible role of liposomes is to assist the proton removal from the reactant, rather than providing the basic interfacial environment.",
keywords = "Horner–Wadsworth–Emmons reaction, Liposome, Phospholipid, Reaction field, Stereochemistry",
author = "Toshinori Shimanouchi and Yuki Kitagawa and Yukitaka Kimura",
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AB - The properties of the liposome membrane as a reaction field were investigated by focusing on the Horner–Wadsworth–Emmons reaction as a case study. Use of the liposomes existing in the gel phase resulted in the enhanced activity of the substrates and furnished the products with same E/Z stereoselectivity as in the liposome-free system. The membrane environment in the gel phase most likely assisted the formation of adducts that induced selective generation of the E-isomer. The possible role of liposomes is to assist the proton removal from the reactant, rather than providing the basic interfacial environment.

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